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[ CAS No. 29079-00-3 ] {[proInfo.proName]}

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Chemical Structure| 29079-00-3
Chemical Structure| 29079-00-3
Structure of 29079-00-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 29079-00-3 ]

CAS No. :29079-00-3 MDL No. :MFCD00102191
Formula : C14H10 Boiling Point : -
Linear Structure Formula :- InChI Key :BPBNKCIVWFCMJY-UHFFFAOYSA-N
M.W : 178.23 Pubchem ID :34464
Synonyms :

Calculated chemistry of [ 29079-00-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.81
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 4.51
Log Po/w (WLOGP) : 3.41
Log Po/w (MLOGP) : 5.24
Log Po/w (SILICOS-IT) : 4.24
Consensus Log Po/w : 4.02

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.35
Solubility : 0.00788 mg/ml ; 0.0000442 mol/l
Class : Moderately soluble
Log S (Ali) : -4.23
Solubility : 0.0105 mg/ml ; 0.0000587 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.99
Solubility : 0.00181 mg/ml ; 0.0000101 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.08

Safety of [ 29079-00-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29079-00-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 29079-00-3 ]

[ 29079-00-3 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 29079-00-3 ]
  • [ 29079-15-0 ]
YieldReaction ConditionsOperation in experiment
100% With 4-(4-bromophenyl)bromobenzene; triethylamine at 59.85℃; for 18h;
98% With piperidine In toluene at 60℃; for 24h; General procedure for the aerobic oxidative homocoupling of terminal alkynes: General procedure: A mixture ofcatalyst (PS-TEDETA-CuSO4, 0.05 mmol of Cu), terminal alkyne (0.5 mmol) and piperidine (0.5mmol) in toluene (1.0 mL) was stirred at 60 oC for 24-48 h under air. After cooling, the mixture wasfiltered, and the residue was washed by dichloromethane (2 mL x3). The combined organic phaseswere concentrated in vacuo and the crude products were purified by column chromatography(hexane/AcOEt) to give the corresponding 1,3-diynes.
97% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; diisopropylamine In tetrahydrofuran at 50℃; for 0.5h;
96% With piperidine; copper(l) chloride In toluene at 60℃; for 5h;
95% With copper(l) iodide; oxygen; triethylamine; palladium dichloride; 3-(diphenylphosphino)propionic acid In N,N-dimethyl-formamide at 20℃; for 24h;
94% With 1,10-Phenanthroline; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 18h;
89% With oxygen In dimethyl sulfoxide at 80℃; for 1h; Green chemistry; General procedure for alkyne homocoupling General procedure: To a solution of terminal alkyne (0.3 mmol) in DMSO (3 mL) was added 5 mol% Cu(II)-clay in a two-neck round bottom flask. A condenser was attached to one neck of this flask, whereas the other neck was closed with a rubber septum. Oxygen was bubbled through a needle inserted through the septum. The resulting mixture was refluxed for the required duration. The reaction was cooled at room temperature and the products were extracted with dichloromethane. The combined organic layers were dried with anhydrous MgSO4, filtered off, and concentrated in vacuo to obtain the crude products, which were purified by silica-gel chromatography to afford the corresponding product.
83% With copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 25℃; 1. General procedure for Copper Catalyzed Homocoupling General procedure: To a 5 mL acetone solution of alkyne (1a: 1 mmol, 0.10 g; 1b: 1 mmol, 0.18 g; 1c: 1 mmol, 0.14g; 1d: 1 mmol, 0.14 g; 1e: 1 mmol, 0.14 g; 1f: 1 mmol, 0.12 g; 1g: 1 mmol, 0.12 g; 1h: 1 mmol,0.12 g; 1i: 1 mmol, 0.12 g; 1j: 1 mmol, 0.13 g; 1k: 1 mmol, 0.13 g; 1l: 1 mmol, 0.18 g; 1m: 1mmol, 0.23 g; 1n: 1 mmol, 0.13 g ), DBU (1 mmol, 0.15 g) and Cu(OTf)2 (5 mmol %, 18 mg) were added and allowed to stir 3-5 hours at rt. When TLC showed full consumption of the starting material, the crude mixture was purified by flash column chromatography on silica gel 60 to obtain the pure product 2.
54% With C38H28O4P2Pd; silver nitrate; triethylamine In tetrahydrofuran; water at 60℃; for 10h; Typical experimental procedure for the homocoupling reactions of terminal alkynes. General procedure: All homocoupling reactions of aromatic terminal alkyneswere carried out under air. A mixture of aromatic terminal alkyne (1.0 mmol), NEt3 (1.0 mmol) and P-O coordinatedcyclopalladated complex 1 (0.005 mmol)/AgNO3 (0.5 mmol) inTHF:H2O (in 4:1 proportion, 2.5 mL) was allowed to react at60°C. The reaction progress was analyzed by GLC. The mixturewas added brine (4 mL) and extracted three times with ethylacetate (3 × 15 mL), dried over Na2SO4, concentrated in vacuoand purifed by thin layer chromatography. The purifed products were identifed by 1H-NMR and 13C-NMR spectroscopy.The Supplemental Materials presents sample 1H and 13C NMRspectra of the diyne products (Figures S1-S24).
33% With pyridine; 1,1’-bis(trimethylsilylethynyl)ferrocene; copper diacetate; potassium carbonate In methanol; chloroform at 50℃; for 10h;
(i) Cu(OAc)2*H2O, Py, MeOH, (ii) aq. H2SO4; Multistep reaction;
With pyridine; copper diacetate

Reference: [1]Constable, Edwin C.; Gusmeroli, Deborah; Housecraft, Catherine E.; Neuburger, Markus; Schaffner, Silvia [Acta Crystallographica, Section C: Crystal Structure Communications, 2006, vol. 62, # 8, p. o505-o509]
[2]Yan, Shuo; Pan, Shiguang; Osako, Takao; Uozumi, Yasuhiro [Synlett, 2016, vol. 27, # 8, p. 1232 - 1236]
[3]Aggarwal, A. Vikas; Jester, Stefan-S.; Taheri, Sara Mehdizadeh; Foerster, Stephan; Hoeger, Sigurd [Chemistry - A European Journal, 2013, vol. 19, # 14, p. 4480 - 4495]
[4]Location in patent: experimental part Zheng, Qingwei; Hua, Ruimao; Wan, Youzhi [Applied Organometallic Chemistry, 2010, vol. 24, # 4, p. 314 - 316]
[5]Liu, Yashuai; Gu, Ningning; Liu, Ping; Xie, Jianwei; Ma, Xiaowei; Liu, Yan; Dai, Bin [Applied Organometallic Chemistry, 2015, vol. 29, # 11, p. 736 - 738]
[6]Vilhanová, Beáta; Václavík, Jiří; Artiglia, Luca; Ranocchiari, Marco; Togni, Antonio; Van Bokhoven, Jeroen A. [ACS Catalysis, 2017, vol. 7, p. 3414 - 3418]
[7]Dar, Bashir Ahmad; Vyas, Dushyant; Shrivastava, Varsha; Farooq, Saleem; Sharma, Amit; Sharma, Sadhana; Sharma, Parduman R.; Sharma, Meena; Singh, Baldev [Comptes Rendus Chimie, 2014, vol. 17, # 4, p. 316 - 323]
[8]Holganza, Maria Katrina; Trigoura, Leslie; Elfarra, Suzanne; Seo, Yoona; Oiler, Jeremy; Xing, Yalan [Tetrahedron Letters, 2019, vol. 60, # 17, p. 1179 - 1181]
[9]Chen, Bo; Guo, Mengping; Wen, Yongju; Shen, Xiuli; Zhou, Xiuling; Lv, Meiyun [Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 3, p. 259 - 263]
[10]Location in patent: experimental part Yoshino, Junro; Shimizu, Rumi; Hayashi, Naoto; Higuchi, Hiroyuki [Bulletin of the Chemical Society of Japan, 2011, vol. 84, # 1, p. 110 - 118]
[11]Ried,W.; Saxena,V.B. [Justus Liebigs Annalen der Chemie, 1970, vol. 739, p. 159 - 165]
[12]Tani,H. et al. [Bulletin of the Chemical Society of Japan, 1963, vol. 36, p. 391 - 396] Nakasuji,K. et al. [Bulletin of the Chemical Society of Japan, 1972, vol. 45, p. 883 - 891]
  • 2
  • [ 29079-00-3 ]
  • [ 77502-93-3 ]
YieldReaction ConditionsOperation in experiment
99% With water-d2 In toluene at 20℃; for 12h;
99% Stage #1: 4-ethynyl-1,1'-biphenyl With potassium carbonate In acetonitrile for 0.5h; Inert atmosphere; Glovebox; Stage #2: With water-d2 In acetonitrile at 20℃; for 12h; Inert atmosphere; Glovebox;
95% With water-d2; di-n-propylamine In 1,4-dioxane at 20℃; for 12h;
With n-butyllithium; water-d2 1.) THF, -78 deg C; 0 deg C, 1 h; Yield given. Multistep reaction;
Stage #1: 4-ethynyl-1,1'-biphenyl With potassium carbonate In acetonitrile for 0.5h; Inert atmosphere; Stage #2: With water-d2 In acetonitrile for 3h; Synthesis of 4-(ethynyl-d)-1,1'-biphenyl 4-ethynyl-1,1'-biphenyl (178 mg, 1 mmol), Potassium carbonate (276 mg, 2 mmol) were added into a flame dried schlenk tube. Schlenk tube was filled with N2 gas, acetonitrile (4 mL) was added into schlenk tube. This was allowed to stir under N2 for 30 minutes. Then D2O (1.5 mL) was added. After 3 hours, the resulting crude reaction mixture was diluted with DCM (10 mL) and transferred to a separating funnel. The organic layer was separated and dried with MgSO4. Further filtration and evaporation of solvent afforded the desired deuterated alkyne.
Stage #1: 4-ethynyl-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Schlenk technique; Stage #2: With water-d2 at -78 - 20℃; for 0.333333h; Schlenk technique;
Stage #1: 4-ethynyl-1,1'-biphenyl With C4H6Zn*LiCl*2MgBr2 In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Glovebox; Stage #2: With water-d2 In tetrahydrofuran

  • 3
  • [ 75867-42-4 ]
  • [ 29079-00-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In methanol; diethyl ether at 20℃; for 0.166667h;
94% With potassium hydroxide In methanol for 1h; Ambient temperature;
92% With potassium carbonate In methanol; diethyl ether for 0.75h; Ambient temperature;
92% With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 2h;
92% With anhydrous potassium trimethylsilanolate In dimethyl sulfoxide at 60℃; for 6h; Sealed tube; 25 4-[(trimethylsilyl)ethynyl]biphenyl (1 mmol), inorganic base potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) (0.05 mmol) , 2 mL of DMA or DMSO solvent was added in turn to a 10 mL sealed tube, heated and stirred in a 60° C. oil bath for 6 hours, and the progress of the reaction was followed according to TLC. The reaction was completed and an equivalent of mesitylene or n-undecane was added as a crude product. Internal standard to determine the exact yield of the product by GC and GC-MS. According to GC and GC-MS, when DMSO is used as a reaction solvent, inorganic base potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) is used as a catalyst, and the yields of the products are as follows: : 71%, 72%, 75%, 71%, 92%, 89%. When DMA was used as the reaction solvent, the inorganic potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) was used as the catalyst. The yield of the product was: 59%, 61%, respectively. 63%, 61%, 73%, 79%.
90% With sodium hydroxide In methanol; diethyl ether at 20℃; for 0.5h;
90% With potassium carbonate In tetrahydrofuran; methanol at 20℃; Synthesis of acetylene derivatives 4e-h General procedure: In a two neck rbf containing THF (100 ml) and MeOH (100 ml)was added compound 3e (7.55 g, 34.43 mmol) at rt. The mixturewas stirred for 5 min followed by addition of K2CO3 (28.55 g,206.58 mmol). The resulting mixture was stirred for 1 h at thesame temperature. The reaction mixture was filtered to removeK2CO3 and then extracted with EtOAc/water. The organic layerwas washed with brine and dried over anhydrous MgSO4. The solventwas evaporated and dried in vacuum to give desired compound4e as a brown solid
57% With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
With potassium carbonate In methanol
With potassium carbonate In tetrahydrofuran; methanol
750 mg With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 0 - 20℃; for 0.5h;
With potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere;
With potassium carbonate In methanol at 20℃; for 2h;
1.22 g With potassium carbonate In methanol at 20℃; for 7.5h;
With potassium carbonate
237 mg With sodium hydroxide In methanol; dichloromethane; lithium hydroxide monohydrate at 20℃; for 2h;
1.44 g With methanol; potassium carbonate In tetrahydrofuran at 20℃; for 2h; 1-Chloro-4-ethynylbenzene (1b) General procedure: According to the reported method, 1 the title compound 1b was prepared from 1-bromo-4-chlorobenzene by the Sonogashira coupling and subsequent desilylation as follows. Under an argon atmosphere, TMSA (2.58 g, 26.2 mmol) was added to a stirred mixture of 1-bromo-4-chlorobenzene (3.83 g, 20.0 mmol), PdCl2(PPh3)2 (350 mg, 0.499 mmol) and CuI (95.2 mg, 0.500 mmol) in Et3N (40 mL). The mixture was heated to 80 °C and stirred for 19 h. The resultant mixture was cooled to room temperature and passed through a short silica gel-activated carbon column. Evaporation of the filtrate under reduced pressure gave a light yellow solid (4.40 g). The crude product was dissolved in MeOH (40 mL) and treated with anhydrous K2CO3 (4.37 g, 31.6 mmol) at room temperature for 15h. The reaction mixture was quenched by dropwise addition of HCl (2 M in H2O, 10 mL) and extracted with CH2Cl2 (3 × 10 mL). The combined organic layer was washed with brine, dried overNa2SO4, and evaporated under reduced pressure. Purification of the residue by silica gel column chromatography (hexane) gave 1b as pale yellow solid (1.23 g, 9.22 mmol, 46%).
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere; Schlenk technique;

Reference: [1]Li; Petersen; Wang [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7804 - 7810]
[2]Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. [Synthesis, 1980, # 8, p. 627 - 630]
[3]John, Jens A.; Tour, James M. [Tetrahedron, 1997, vol. 53, # 45, p. 15515 - 15534]
[4]Aggarwal, A. Vikas; Jester, Stefan-S.; Taheri, Sara Mehdizadeh; Foerster, Stephan; Hoeger, Sigurd [Chemistry - A European Journal, 2013, vol. 19, # 14, p. 4480 - 4495]
[5]Current Patent Assignee: TAIZHOU UNIVERSITY - CN107459438, 2017, A Location in patent: Paragraph 0064; 0065
[6]Feng, Yi-Si; Xie, Chuan-Qi; Qiao, Wen-Long; Xu, Hua-Jian [Organic Letters, 2013, vol. 15, # 4, p. 936 - 939]
[7]Singh, Sarbjit; Goo, Ja-Il; Noh, Hyojin; Lee, Sung Jae; Kim, Myoung Woo; Park, Hyejun; Jalani, Hitesh B.; Lee, Kyeong; Kim, Chunsook; Kim, Won-Ki; Ju, Chung; Choi, Yongseok [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 4, p. 1394 - 1405]
[8]Okugawa, Yuto; Hirano, Koji; Miura, Masahiro [Angewandte Chemie - International Edition, 2016, vol. 55, # 43, p. 13558 - 13561][Angew. Chem., 2016, vol. 128, # 43, p. 13756 - 13759]
[9]Ghazala, Safaa Ibn; Paul, Frederic; Toupet, Loic; Roisnel, Thierry; Hapiot, Philippe; Lapinte, Claude [Journal of the American Chemical Society, 2006, vol. 128, # 7, p. 2463 - 2476]
[10]Chan, Carrie Y. K.; Tseng, Nai-Wen; Lam, Jacky W. Y.; Liu, Jianzhao; Kwok, Ryan T. K.; Tang, Ben Zhong [Macromolecules, 2013, vol. 46, # 9, p. 3246 - 3256]
[11]Handa, Sachin; Fennewald, James C.; Lipshutz, Bruce H. [Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3432 - 3435][Angew. Chem., 2014, vol. 126, # 13, p. 3500 - 3503,4]
[12]Lin, Yuanguang; Song, Qiuling [European Journal of Organic Chemistry, 2016, vol. 2016, # 18, p. 3056 - 3059]
[13]Bai, Yu-Bin; Luo, Zaigang; Wang, Yuguang; Gao, Jin-Ming; Zhang, Liming [Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5860 - 5865]
[14]Zhang, Xingjie; Xie, Xin; Liu, Yuanhong [Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7385 - 7389]
[15]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN110437277, 2019, A Location in patent: Paragraph 0023
[16]Bédard, Sandrine; Cavallo, Luigi; Falivene, Laura; Gauthier, Raphaël; Nolan, Steven P.; Paquin, Jean-François; Saab, Marina; Tzouras, Nikolaos V.; Van Hecke, Kristof; Zhang, Ziyun [Chemistry - A European Journal, 2022, vol. 28, # 4]
[17]Kumaki, Wataru; Kinoshita, Hidenori; Miura, Katsukiyo [Tetrahedron, 2022, vol. 110]
[18]Pan, Shitao; Xie, Qiqiang; Wang, Xiu; Wang, Qian; Ni, Chuanfa; Hu, Jinbo [Chemical Communications, 2022, vol. 58, # 33, p. 5156 - 5159]
  • 4
  • [ 29079-00-3 ]
  • [ 121-69-7 ]
  • N-(3-([1,1'-biphenyl]-4-yl)prop-2-yn-1-yl)-N-methylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylhydroperoxide In 1,2-dichloro-ethane at 70℃; for 4h; General procedure for the CDC reaction General procedure: At room temperature, Cu(II)-AOFs (Cu(II): 4.41 mol%,0.0764 g) was added to a solution of terminal alkynes 2 (1.3mmol), N,N-dimethylanilines 1 (1 mmol) and TBHP (1 mmol)in DCE (2 mL). The resulting mixture was vigorously stirredin an oil bath at 70 °C for 4 h. After cooling to room temperature,the Cu(II)-AOFs catalyst was separated by filtration, andthen washed with ethyl acetate and distilled water. Finally, thewashed catalyst was dried for half an hour at 50 °C and reusedin the next experiment. The reaction mixture was extractedthree times with ethyl acetate and the combined organicswashed with distilled water. The organic layers were driedover anhydrous magnesium sulfate and concentrated by rotaryevaporation to remove the solvent. The residue was purifiedby the silica gel column chromatography (eluent:petroleumether/ethyl acetate = 50:1) to afford the final coupling product.As for known coupling products, only 1H NMR and 13CNMR spectra were confirmed with previously reported literature,and the new compounds were characterized by 1H NMR,13C NMR spectra, IR, and mass spectra.
68% With tert.-butylhydroperoxide; copper(I) bromide In decane at 100℃; for 3.25h; Inert atmosphere;
60% With tert.-butylhydroperoxide; copper(I) bromide In decane at 100℃; for 3h;
  • 5
  • [ 201230-82-2 ]
  • [ 29079-00-3 ]
  • [ 278603-80-8 ]
  • 7-biphenyl-4-yl-6-hydroxy-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: carbon monoxide; 4-ethynyl-1,1'-biphenyl; 1-(2-methoxyethoxy)-1-vinylcyclopropane With di(rhodium)tetracarbonyl dichloride In toluene at 60℃; for 30h; Stage #2: With silica gel In dichloromethane
  • 6
  • [ 591-50-4 ]
  • [ 29079-00-3 ]
  • [ 15784-39-1 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In ethanol at 80℃; for 6h;
95% With (diphenylphosphin)ferrocene; gold(I) iodide; potassium carbonate In toluene at 130℃; for 24h;
94% With potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 8h;
93% With potassium carbonate In ethanol at 80℃; for 6h;
181 mg With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In 1,4-dioxane at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere;

  • 7
  • [ 90965-06-3 ]
  • [ 3218-36-8 ]
  • [ 29079-00-3 ]
YieldReaction ConditionsOperation in experiment
82% With potassium <i>tert</i>-butylate In methanol at 100℃; for 0.5h;
33 mg With potassium carbonate In tetrahydrofuran; methanol at 20℃;
With potassium carbonate In methanol at 60℃; for 0.75h; Microwave irradiation;
  • 8
  • [ 14243-64-2 ]
  • [ 29079-00-3 ]
  • 4-phenylphenylethynyl(triphenylphosphine)gold [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium ethanolate; In ethanol; for 1.5h;Heating / reflux; Under an argon atmosphere, Au(PPh3)Cl (1.0 g, 2.02 mmol), 4-phenylphenylethyne (540 mg, 3.03 mmol) and ethanol (35 ml) were added to a 20 ml Schlenk tube, and then sodium ethoxide (0.83 ml, 2.12 mmol: 2.55 mol/l (liter) in ethanol solution) was added dropwise thereto and the mixture was heated under reflux for 1.5 hours. The reaction mixture was cooled to room temperature and the resulting white precipitate was filtered and successively washed with ethanol (20 ml×three times), water (20 ml×three times) and ethanol (20 ml×three times), followed by drying under vacuum to give 1.26 g of the desired compound as a white powder (yield: 98%). 1H-NMR (400 MHz, CDCl3) δ: 7.60-7.40 (m, 23H), 7.34-7.29 (m, 1H) (FAB-MS) (M/Z): 637 (M+H)+ Elemental analysis: Found C: 59.96, H: 3.86 Theoretical C: 60.39, H: 3.80
  • 9
  • [ 29079-00-3 ]
  • [ 90-02-8 ]
  • [ 42327-62-8 ]
YieldReaction ConditionsOperation in experiment
63% With tributylphosphine In toluene at 150℃; for 36h;
26.2% With gold(I) cyanide; tributylphosphine In toluene at 150℃; for 36h; 5.1.1.1. Method A (Thermal Process) General procedure: To a 5-mL micro reaction vial equipped with a stirring bar was added AuCN (0.03 mmol, 0.03 equiv, 6.6 mg), Bu3P(0.75 mmol, 0.75 equiv, 185.1 μL), aldehyde (1 mmol, 1 equiv), alkyne (3 mmol, 3 equiv) and 4 mL of freshly distilled toluene. The reaction mixture was stirred at 150 °C for 36 h. After cooling down to room temperature, the crude mixture was loaded directly on silica gel and was purified by Medium Performance Liquid Chromatography, eluding with an ethyl acetate/hexanes gradient to afford the desired products.
  • 10
  • [ 29079-00-3 ]
  • [ 15796-82-4 ]
  • C35H36O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In DMF (N,N-dimethyl-formamide) at -10 - 20℃; for 2.58333h; 2 Preparation of the propargyl alcohol, PA-2: Under a nitrogen atmosphere, 4-biphenylacetylene (32.76 g of 97%, 178.31 mMole), was dissolved in dimethylformamide (DMF) (750 mL), stirred with a mechanical stirrer and the solution cool to -10° C. to OC. Powdered potassium t-butoxide (KButO) (25 g of 95%, 213.97 mMole), was added over a 10-minute period and the mixture stirred well for approximately 15 minutes at -10° C. to 0° C. To this mixture was then added 4,4'-di-tert-butylbenzophenone (50 g, 169.81 mMole) all at once. Stirring was continued at -10° C. to 0° C. for approximately 1 hour and then allowed to come to room temperature over a 1-hour period. At the end of this time the solution was cooled to 0° C. and the reaction treated with saturated sodium chloride (100 mL), keeping the temperature below 10° C. The mixture was then diluted with ethyl acetate, washed with 2N-HCl (3×100 mL), dried over MgSO4, treated with decolorizing charcoal (×2), filtered and concentrated under reduced pressure. The crude product was triturated with ether (200 mL) and heptane (500 mL) to give the product as an off-white solid. Yield of propagyl alcohol PA-2, 72 g. Preparation of Naphthacene Compound, YD-2: Propargyl alcohol PA-2, (5.0 g, 10 mMole) was dissolved in toluene (70 mL), with slight heating to get complete dissolution, cooled and stirred at 0° C. under a nitrogen atmosphere. To this solution was added triethylamine (NEt3), (1.41 g, 1.81 mL, 14 mMole) and then treated drop-by-drop with methanesulfonyl chloride (CH3SO2Cl), (1.79 g, 1.21 mL 14 mMole), keeping the temperature of the reaction below 10° C. After the addition, the solution was stirred at 0° C. for 15 minutes and then at room temperature for 15 minutes. To the reaction mixture was then added finely powered anhydrous Na2CO3 (2.11 g, 20 mMole) and then heated, with good stirring, to 110° C. for 4 hours. After this period, the reaction was cooled, diluted with ethyl acetate (100 mL) and carefully washed with 2N-HCl until acidic. On standing, the product crystallized out. It was filtered off, washed well with methanol and dried. Yield, YD-2, 6.0 g.
With potassium <i>tert</i>-butylate In DMF (N,N-dimethyl-formamide) at -10 - 20℃; for 2.58333h; 2 Preparation of the propargyl alcohol, PA-2: Under a nitrogen atmosphere, 4-biphenylacetylene (32.76 g of 97%, 178.31 mMole), was dissolved in dimethylformamide (DMF) (750 mL), stirred with a mechanical stirrer and the solution cool to -10° C. to 0° C. Powdered potassium t-butoxide (KButO) (25 g of 95%, 213.97 mMole), was added over a 10-minute period and the mixture stirred well for approximately 15 minutes at -10° C. to 0° C. To this mixture was then added 4,4'-di-tert-butylbenzophenone (50 g, 169.81 mMole) all at once. Stirring was continued at -10° C. to 0° C. for approximately 1 hour and then allowed to come to room temperature over a 1-hour period. At the end of this time the solution was cooled to 0° C. and the reaction treated with saturated sodium chloride (100 mL), keeping the temperature below 10° C. The mixture was then diluted with ethyl acetate, washed with 2N-HCl (3×100 mL), dried over MgSO4, treated with decolorizing charcoal (×2), filtered and concentrated under reduced pressure. The crude product was triturated with ether (200 mL) and heptane (500 mL) to give the product as an off-white solid. Yield of propagyl alcohol PA-2, 72 g. Preparation of Naphthacene Compound, YD-2: Propargyl alcohol PA-2, (5.0 g, 10 mMole) was dissolved in toluene (70 mL), with slight heating to get complete dissolution, cooled and stirred at 0° C. under a nitrogen atmosphere. To this solution was added triethylamine (NEt3), (1.41 g, 1.8 l mL, 14 mMole) and then treated drop-by-drop with methanesulfonyl chloride (CH3SO2Cl), (1.79 g, 1.21 mL 14 mMole), keeping the temperature of the reaction below 1° C. After the addition, the solution was stirred at 0° C. for 15 minutes and then at room temperature for 15 minutes. To the reaction mixture was then added finely powered anhydrous Na2CO3 (2.11 g, 20 mMole) and then heated, with good stirring, to 110° C. for 4 hours. After this period, the reaction was cooled, diluted with ethyl acetate (100 mL) and carefully washed with 2N-HCl until acidic. On standing, the product crystallized out. It was filtered off, washed well with methanol and dried. Yield, YD-2, 6.0 g.
With potassium <i>tert</i>-butylate In DMF (N,N-dimethylformamide) at -10 - 20℃; for 2.41667h; 2 Under a nitrogen atmosphere, 4-biphenylacetylene (32.76 g of 97%, 178.31 mMole), was dissolved in dimethylformamide (DMF) (750 mL), stirred with a mechanical stirrer and the solution cool to -10° C. to 0° C. Powdered potassium t-butoxide (KButO) (25 g of 95%, 213.97 mMole), was added over a 10-minute period and the mixture stirred well for approximately 15 minutes at -10° C. to 0° C. To this mixture was then added 4,4'-di-tert-butylbenzophenone (50 g, 169.81 mMole) all at once. Stirring was continued at -10° C. to 0° C. for approximately 1 hour and then allowed to come to room temperature over a 1-hour period. At the end of this time the solution was cooled to 0° C. and the reaction treated with saturated sodium chloride (100 mL), keeping the temperature below 10° C. The mixture was then diluted with ethyl acetate, washed with 2N-HCl (3×100 mL), dried over MgSO4, treated with decolorizing charcoal (x2), filtered and concentrated under reduced pressure. The crude product was triturated with ether (200 mL) and heptane (500 mL) to give the product as an off-white solid. Yield of propargyl alcohol PA-2, 72 g.
Stage #1: 4-ethynyl-1,1'-biphenyl With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -10 - 0℃; for 0.416667h; Stage #2: 4,4'-di-tert-butylbenzophenone In N,N-dimethyl-formamide at -10 - 20℃; for 2h; 1 Preparation of the propargyl alcohol, Int-1: Under a nitrogen atmosphere, 4-biphenylacetylene (32.76 g of 97%, 178.3 lmMole), was dissolved in dimethylformamide (DMF) (750mL), stirred with a mechanical stirrer and the solution cool to -10° C. to 0° C. Powdered potassium t-butoxide (KButO) (25 g of 95%, 213.97 mMole), was added over a 10-minute period and the mixture stirred well for approximately 15 minutes at -10+ C. to 0° C. To this mixture was then added 4,4'-di-tert-butylbenzophenone (50 g, 169.81 mMole) all at once. Stirring was continued at -10° C. to 0° C. for approximately 1 hour and then allowed to come to room temperature over a 1-hour period. At the end of this time the solution was cooled to 0° C. and the reaction treated with saturated sodium chloride (100 mL), keeping the temperature below 10° C. The mixture was then diluted with ethyl acetate, washed with 2N-HCl (3×100 mL), dried over MgSO4, treated with decolorizing charcoal (×2), filtered and concentrated under reduced pressure. The crude product was triturated with ether (200 mL) and heptane (500 mL) to give the product as an off-white solid. Yield of propagyl alcohol Int-1, 72 g.

  • 11
  • [ 1041180-31-7 ]
  • [ 29079-00-3 ]
  • [ 1041180-37-3 ]
YieldReaction ConditionsOperation in experiment
87% With silver hexafluoroantimonate In water at 75℃; for 26h;
  • 12
  • [ 29079-00-3 ]
  • [ 60169-72-4 ]
  • [ 1133437-58-7 ]
YieldReaction ConditionsOperation in experiment
80% With N,N,N,N,-tetramethylethylenediamine; di-tert-butyl peroxide; copper(I) bromide In toluene at 110℃; Inert atmosphere;
70% With N,N,N,N,-tetramethylethylenediamine; di-tert-butyl peroxide; copper(I) bromide In toluene at 110℃; for 12h; Inert atmosphere; Schlenk technique;
  • 13
  • [ 124-38-9 ]
  • [ 29079-00-3 ]
  • [ 32340-38-8 ]
YieldReaction ConditionsOperation in experiment
92% General procedure: The terminal alkyne (1.0 mmol) was added to a mixtureof HSi(OEt)2Me (5.0 mmol) and KOtBu (1.5 mmol) in a10 mL Schlenk tube with a magnetic stirrer. The Schlenktube was evacuated and back-filled with CO2 for 3 times.After a CO2 ballon was connected, the reactor was moved toa water bath of 40 C. After being stirred for 2 h, the reactionmixture was diluted with water (30 mL), and was extractedwith CH2Cl2 (3×10 mL). The aqueous layer was acidifiedwith aqueous HCl (6 M) and then extracted with diethylether (5×20 mL). The combined organic extracts were driedover Na2SO4 and concentrated under vacuum to give the purepropiolic acid (such as compound 3-phenylpropiolic acid(3a): 98%).
88% Sequentially adding a catalyst in the reaction bottle (14.0 mg, 0.025 millimole, 5mol %), cesium carbonate (32.6 mg, 1.0 mmol), 4-ethynyl biphenyl (89.1 mg, 0.5 mmol),N,N-dimethylformamide(3 ml), into the carbon dioxide, in the 65 C, reaction under normal pressure 18 hours. Reaction cooling to room temperature, diluted with water, acidified with hydrochloric acid, diethyl ether extraction, washing with saturated sodium chloride for ether level, dry anhydrous sodium sulfate, obtained product is vacuum to remove the solvent, the yield is 88%.
86% With caesium carbonate; In dimethyl sulfoxide; at 60℃; for 24h;Sealed tube; Inert atmosphere; Under sealed conditions without water and oxygen, argon protection,0.6516 g of Cs2CO3 (2 mmol, 2 equiv.) was weighed into the reaction flask.A small syringe was charged with 0.1782 g (1 mmol, 1 equiv.) of 4-ethynylbiphenyl.The syringe was added with 5 mL of DMSO, and the CO 2 gas was used to displace the air in the reaction system.The reaction was carried out at 60 C for 24 h. After the reaction, the mixture was exposed to air, cooled slightly at room temperature, and then cooled in an ice water bath.Add 10 mL of deionized water, and add 20 mL of 6 mol/L HCl solution to fully acidify.The organic phase was combined and the organic phase was washed with brine brine.The organic phase is separated and dried with anhydrous Na2SO4.The solvent is removed under reduced pressure to obtain the desired product.The isolated yield was 86%.
83% With caesium carbonate; In dimethyl sulfoxide; at 60℃; under 760.051 Torr; for 24h; Add 4 ml of dimethyl sulfoxide, 1 mmol of 4-ethynylbiphenyl, 2 mmol of cesium carbonate into the reaction tube,The reaction tube was pumped and ventilated 3 times, and filled with CO2. After the CO2 was filled, the gas pressure of the reaction tube was 1 atm. The reaction tube was stirred for 24 hours under the conditions of carbon dioxide atmosphere and 60C. The stirring rate is 800 rpm, stop stirring, and cool to room temperature.Add water to the reaction solution, extract 4 times with ethyl acetate, separate the layers, take the aqueous layer, acidify the aqueous layer with 2 moles of hydrochloric acid per liter to pH=1, then extract with ethyl acetate, take the organic layer, and wash the organic layer with saturated brine It was dried over magnesium sulfate, the filtrate was filtered, and concentrated under reduced pressure to obtain the target product with a yield of 83%.

  • 14
  • [ 29079-00-3 ]
  • [ 622-79-7 ]
  • [ 1188337-88-3 ]
YieldReaction ConditionsOperation in experiment
99% With copper(I) complex of phenanthroline-modified chitosan In ethanol at 70℃; for 14h;
99% With Cu(OAc)2-anchored mesoporous SBA-15 catalyst (CuSBA-15-PTAA) In water at 50℃; for 8h;
92% With [(1-phenylisoquinoline)2Ir(acetylacetonate)] In dichloromethane at 20℃; Irradiation; regioselective reaction;
92.4% With Cu8I8*2C60H52N4O8S4 In water; acetonitrile at 20℃; for 8h; Irradiation;
73% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) iodide; triethylamine In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;
With ethylene diamine functionalized cellulose on SiO2 composite-supported Cu(0)-Fe3O4 nanoparticle catalyst In water at 20℃; for 5h; Green chemistry; 2.7 General Procedure for the Cu(0)-Fe3O4SiO2/NH2cel Catalyzed One-Pot Synthesis of 1,4-Disubstituted-1,2,3-triazoles General procedure: To a round bottomed flask maintained at 0-5 °C, aryl amine (2 mmol), and conc. HCl: H2O (1.5 mL, 1:1) were added, and the reaction mixture was stirred for 5 min. Then, solution of NaNO2 (2.5 mmol in 1 mL water) was added dropwise to the reaction mixture over a period of 5 min while maintaining the temperature of round bottomed flask at 0-5 °C. After stirring for another 5 min, sodium azide (3 mmol) was added, and the reaction mixture was further stirred for 10 min. Finally, aryl alkyne (1.5 mmol) and Cu(0)-Fe3O4-SiO2/EDAcel (0.05 g, 0.25 mol% Cu) were added to the reaction mixture followed by stirring at room temperature for the appropriate time (Scheme 2). After completion of the reaction (monitored by TLC), the catalyst was separated using an external magnet and the reaction mixture was diluted with ethyl acetate and filtered. The organic layer was washed with water and dried over anhyd. Na2SO4. Finally, the solvent was removed under pressure and the residue was crystallized from EtOAc-pet. ether to get the product. The recovered catalyst was washed with EtOAc (2 x 10 mL) followed by double distilled water (2 x 10 mL). It was dried and then reused for subsequent reactions.

  • 15
  • [ 875-30-9 ]
  • [ 29079-00-3 ]
  • [ 1235886-00-6 ]
YieldReaction ConditionsOperation in experiment
72% With potassium tetrachloropalladate(II); oxygen; caesium carbonate; Trimethylacetic acid In dimethyl sulfoxide at 80℃; for 24h;
  • 16
  • [ 29079-00-3 ]
  • [ 28179-30-8 ]
YieldReaction ConditionsOperation in experiment
92% With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.333333h; typical procedure for preparation of a,a-dichloroketons and a,a-dibromoketones General procedure: 1-Ethynyl-4-methylbenzene 1b (0.5 g, 4.3 mmol), KBr (1.0 g, 8.6 mmol),oxone (5.3 g, 8.6 mmol), and acetonitrile (10 mL) were taken into a 100 mL round bottomed flask and stirred at room temperature.Next, water (5 mL) was added dropwise to the mixture. With the addition of water,exothermicreaction was observed and temperature of the reaction mixture increased to 50 C. After completion of the reaction (TLC), reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3 15 mL). The combinedorganic layers were washed with brine, dried over anhyd. Na2SO4, andconcentrated under reduced pressure. Purification of the crude product bynormal column chromatography (silica gel 60-120 mesh, n-hexane) furnished2,2-dibromo-1-p-tolylethanone 3b (1.22 g, 97%) as a pale yellow solid
84% With N-Bromosuccinimide In water; acetone at 20℃; for 0.666667h; Green chemistry; regioselective reaction; General procedure for synthesis of α,α-dibromoketone using Sol Gel Polymer P1 General procedure: To a solution of alkyne (0.5 mmol), NXS (2.00 mmol), acetone (3 mL), H2O (2.5 mmol)and Sol Gel polymer (15% wt.). The reaction solution was stirring 40 min at room temperature.When TLC showed full consumption of starting material, reaction was placed in a centrifugedtube. Supernatant was separated from the Sol Gel polymer and filtered. Filtrate was collected andsolvent was removed using the rotary evaporator. The mixture was purified by flashchromatography on Silica Gel 60 to give pure product
72% With sodium hydrogensulfate monohydrate; water; sodium bromide In acetonitrile at 20℃; for 8h; Schlenk technique;
71% With water; hydrogen bromide; oxygen In acetonitrile for 10h; Irradiation;

  • 17
  • [ 29079-00-3 ]
  • methyl 2-amino-3-iodobenzoate [ No CAS ]
  • [ 1248542-23-5 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine In tetrahydrofuran at 20℃; 61.5 Step 5: 2-Biphenyl-4-yl-1H-indole-7-carboxylic acid; To a solution of 2-amino-3-iodo-benzoic acid methyl ester (500 mg, 1.8 mmol), 4- ethynyl-biphenyl (416 mg, 2.3 mmol) in THF (20 ml_), CuI (17 mg, 0.09 mmol), bis- (triphenylphosphine)-palladium (ll)-chloride (64 mg, 0.09 mmol) and TEA (0.75 ml_, 5.4 mmol) were added. This mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion, the reaction mass was filtered through celite, and the collected filtrate was diluted with ethyl acetate (30 ml_), washed with water (2x20 ml.) and the combined organic layer was separated and dried over sodium sulphate and concentrated under reduced pressure to obtain brown mass which was purified by column chromatography using 5% ethyl acetate in hexane as an eluent to obtain 450 mg of 2-amino-3-biphenyl-4-ylethynyl-benzoic acid methyl ester as a pale yellow coloured solid (76%).1H NMR (300 MHz, CDCI3): δ (ppm) = 7.81 (dd, 1 H, J1=S-I Hz, J2=8.1 Hz), 7.57-7.18(m, 10H), 6.56(t, 1 H, J=7.5Hz), 6.44(br.s, 2H), 3.81 (s, 3H).To a cold solution of 2-amino-3-biphenyl-4-ylethynyl-benzoic acid methyl ester (300 mg, 0.91 mmol) in NMP (5 ml.) was added dropwise a solution of potassium t-butoxide (205 mg, 1 .83 mmol) in N MP (5 ml_). This reaction mixture was allowed to stir at room temperature for 5 h. After the reaction is completed it was poured into water and pH was adjusted to 2. The resulting precipitate was collected by filtration and was washed with water. Finally it was dried in a vacuum oven to get the 145 mg of 2-biphenyl-4-yl-1 H- indole-7-carboxylic acid as a pale yellow coloured solid. 1H NMR (300 MHz, DMSOd6): δ (ppm) = 13.05(s, 1 H) 10.75(s, 1 H) 8.00(d, 2H, J=8.4 Hz), 7.86-7.73(m, 5H) 7.50(t, 2H, J=7.28 Hz), 7.41-7.36(m, 1 H), 7.15(t, 1 H, J=7.8Hz), 7.09(d, 1 H, J=2.4Hz). HPLC purity: 84.78%
  • 18
  • [ 592-35-8 ]
  • [ 29079-00-3 ]
  • [ 100-52-7 ]
  • [ 1261030-52-7 ]
  • 19
  • [ 100125-12-0 ]
  • [ 29079-00-3 ]
  • [ 1256157-71-7 ]
  • 20
  • [ 29079-00-3 ]
  • [ 1189797-63-4 ]
  • [ 1189797-97-4 ]
YieldReaction ConditionsOperation in experiment
69% With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 18h; Sealed tube; Inert atmosphere; 5.27. 2-(4-Methylphenyl)-9-phenylethynyl-2,6-dihydro[1,2,4]triazolo[4,3-c]-quinazoline-3,5-dione (13) General procedure: To a stirred solution of phenylacetylene (15.0 μL, 0.137 mmol) and 8a (25.3 mg, 0.0682 mmol) in a mixture of 2 mL of DMF and 1 mL of NEt3, was added Pd(OAc)2 (1.53 mg, 6.82 μmol) and triphenylphosphine (3.57 mg, 13.6 μmol) in a seal tube. The tube was sealed under argon and the mixture was stirred at 100 °C for 18 h. The mixture was cooled and concentrated to dryness in vacuo and the crude product was purified by chromatography on a silica gel column. Elution with n-heptane/EtOAc (2:1) as eluent yielded 13 as a white solid (14 mg, 70%).
  • 21
  • [ 29079-00-3 ]
  • [ 244138-64-5 ]
  • [ 1300698-52-5 ]
YieldReaction ConditionsOperation in experiment
70% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; 6.1.12. General procedure for synthesis of compounds 13a-13i General procedure: A mixture of 12a (201.8 mg, 0.3 mmol), Pd(PPh3)4 (17.3 mg, 0.015 mmol), Et3N (0.22 mL, 1.5 mmol), CuI (5.7 mg, 0.03 mmol) and monosubstituted alkynes 13a-13i (0.9 mmol) in DMF (6.0 mL) was stirred at 80 °C for 3 h under argon atmosphere. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was cooled to room temperature, diluted with Et2O (25 mL), washed with a saturated aqueous NH4Cl solution (3 × 10 mL), dried over Na2SO4, filtered and concentrated in vacuum. The crude product was purified by silica gel column chromatography to give the pure product.
  • 22
  • [ 29079-00-3 ]
  • [ 166392-81-0 ]
  • [ 1313271-89-4 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 4-ethynyl-1,1'-biphenyl; methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate With Rh2(S-PTAD)4 In dichloromethane at 0℃; for 2.5h; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In dichloromethane at 23℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction; 4.3. General procedure for Rh(II)-catalyzed decompositions of siloxyvinyldiazoacetate 5 in the presence of acetylenes General procedure: A mixture of alkyne 6 (0.5 mmol) and Rh2(S-PTAD)4 (0.01 mmol) was dissolved in 1 mL of dichloromethane and stirred at -45 °C under an atmosphere of argon. Siloxyvinyldiazoacetate 5 (1.0 mmol) in 10 mL dichloromethane was then added to the reaction mixture via syringe pump over 2 h. After the complete addition, the reaction mixture was stirred for additional 20 min followed by addition of TBAF (1.0 mmol) in one portion. The reaction mixture was further stirred at 23 °C followed by aqueous work-up. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified on silica using 10:1 hexane/diethyl ether followed by 1:1 hexane/EtOAc as eluents to afford the desired cyclopropenyl ketones.
  • 23
  • [ 29079-00-3 ]
  • [ 1321929-32-1 ]
YieldReaction ConditionsOperation in experiment
55% With N-Bromosuccinimide; silver nitrate; In acetone; at 20℃; for 2h; General procedure: Phenylacetylene (1.86 g, 2 mL, 18.2 mmol) was dissolved in acetone (91 mL). NBS (1.1 eq.,3.56 g, 20 mmol) and AgNO3 (0.1 eq., 309 mg, 1.82 mmol) were added to the solution and themixture was stirred at room temperature for 2 hours. After the complete consumption of thestarting material (TLC 100% petroleum ether), the reaction was concentrated under vacuum,diluted with hexane and then filtered on a pad of silica gel and washed with hexane. The filtratewas evaporated under vacuum to give (2-bromoethynyl)benzene 11a (2.71 g, 15 mmol, 82%)as a colorless oil.
With N-Bromosuccinimide; silver nitrate; In acetone; at 20℃; for 3h; General procedure: To the mixture of terminal alkyne (1 mmol), NBS (1.2 mmol) and 10 mL acetone, AgNO3 (5 mol %) was added and the mixture was stirred at room temperature for three hours. After the reaction completion, the solvent was evaporated and extracted with 10 mL petroleum ether (30-60C), then evaporated the solvent and the residue was the title product.
  • 24
  • [ 29079-00-3 ]
  • (E)-4-phenylstyrylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With benzo[1,3,2]dioxaborole at 70℃; for 1h; Inert atmosphere; General Procedure for Generation of Vinylboronic acids (5n-p) from Hydroboration/Hydrolysis General Procedure for Generation of Vinylboronic acids (5n-p) from Hydroboration/Hydrolysis. To a dried (120oC, overnight) 10 mL round bottom flask charged with stir bar the appropriate aryl ethynyl starting material was added and degassed under Ar for 30 min. 3.0 equivalents of catecholborane neat was added and the resulting mixture was submerged in a heated oil bath (40oC). The mixture was heated to 70oC and stirred for 1 hr. The solution was allowed to cool to room temperature at which point H2O (10 mL) was added. The resulting solution was transferred to an Erlenmeyer flask, more H2O (~50 mL) was added and the solution was mixed for 1 hr at 25 oC. The resulting solid was vacuum filtered and recrystallized with boiling H2O (E)-2-(Biphenyl-4-yl)vinylboronic acid (5n). ; 4-ethynylbiphenyl (Aldrich) (178.2 mg, 1.0 mmol) reacted with catecholborane neat (0.32 mL, 3.0 mmol) to afford 115 mg of a creamy orange solid 5n [2] after recrystallization (51%). mp 117-130 oC. 1H NMR (d6-acetone, 300 MHz): δ 6.23 (d, J = 18.6 Hz, 1H, vinyl-H), 7.36 (t, J = 6.3 Hz, 1H, H8), 7.39-7.46 (m,d, 4H, H2, H7), 7.59-7.70 (m, 4H, H3, H6). 13C NMR (d6-acetone, 75.4 MHz): δ 146.33 (ethenyl-C2), 141.14 (C5), 140.59 (C4), 137.40 (C1), 129.12 (C7), 127.60 (C8), 127.59 (C6), 127.28 (C3), 126.93 (C2).
Multi-step reaction with 2 steps 1: tetrahydrofuran / 70 °C 2: water
Multi-step reaction with 2 steps 1.1: copper; sodium methylate / ethanol; 1,4-dioxane / 0.5 h / Inert atmosphere; Schlenk technique 1.2: 12 h / 60 °C / Inert atmosphere; Schlenk technique 2.1: sodium periodate / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere 2.2: 17 h / 20 °C / Inert atmosphere
  • 25
  • [ 29079-00-3 ]
  • [ 2350-89-2 ]
YieldReaction ConditionsOperation in experiment
75% With palladium diacetate; (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane; In ethanol; acetonitrile; at 80℃; for 24h;Inert atmosphere; Under the protection of N2, 4-ethynylbiphenyl (0.20 mmol) and Pd(OAc) 2 (0.02 mmol, were added to a 15 ml pressure-resistant tube.4.48 mg), R, R-DIPAMP (0.2 mmol, 18.32 mg), 95% EtOH (10 mmol, 595 L) and CH3CN (1.5 mL), 80The reaction was stirred at C for 24 hours.After completion of the reaction, the mixture was cooled to room temperature, and ethyl acetate (10 mL) was evaporated. The crude product was separated and purified by column chromatography to obtain 4-vinylbiphenyl, a colorless liquid, 15.8 mg, yield 75%.
  • 26
  • [ 16029-98-4 ]
  • [ 29079-00-3 ]
  • [ 75867-42-4 ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine In toluene at 80℃; Inert atmosphere; 22 Example 21A reactor with a capacity of 40 mL, equipped with a magnetic stirrer was filled, under argon atmosphere, with 0.0085 g (0.015 mmol) of [{Ir^-Cl)(CO)2}2], and then with 8 mL of anhydrous and deoxidized toluene and 0.7g (5.4 mmol) of NEt(z-Pr)2. The whole mixture was stirred until the starting iridium(I) complex was dissolved, and then 0.535g (3mmol) of 4- ethynylbiphenyl and 0.96 g (4.8 mmol) of ISiMe3 were added to the resulting mixture. The reaction was carried out at a temperature of 80°C until complete conversion of 4- ethynylbiphenyl. After the reaction was completed, in order to remove the catalyst from the reaction mixture the solvent was evaporated at a reduced pressure along with any residual unreacted substrates. The silylation product was extracted by means of pentane using a cannula system. The solvent was initially evaporated from the extract, and then raw product was purified on a Si02-packed column (modified with a 15%> hexane solution of Et3N), using hexane as eluent. The product was 0.706 g of 4-(trimethylsilylethynyl)biphenyl, obtained with a yield of 94%.Example 22Following the procedure used in Example 21, a reaction was carried out between:- 1.07 g (6 mmol) of 4-ethynylbiphenyl- 1.92 g (9.6 mmol) of ISiMe3 in the presence of- 0.017 g (0.03 mmol) of the complex [{Ir^-Cl)(CO)2}2] - 1.40 g (10.8 mmol) of NEt(z-Pr)2 The product was 1.44g of 4-(trimethylsilylethynyl)biphenyl, obtained with a yield of 96%.
96% With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine In toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere; 2.Synthesis of (arylethynyl)trisubstituted silanes General procedure: Synthesis of 4-(trimethylsilylethynyl)biphenyl(3) A reactor with a capacity of 40 mL, equippedwith a magnetic stirrer was charged, under argon atmosphere, with 0.0085 g(0.015 mmol) of [{Ir(µ-Cl)(CO)2}2],and then with 20 mL of anhydrous and deoxidized toluene and 0.7g (5.4 mmol) ofNEt(i-Pr)2.The whole mixture was stirred until the starting iridium(I) complex wasdissolved, and then 0.535g (3mmol) of 4-ethynylbiphenyl and0.96 g (4.8 mmol) of ISiMe3were added to the resulting mixture. The reaction was carried out at a temperature of 80oC untilcomplete conversion of 4-ethynylbiphenyl. After the reaction was completed, in order to remove the catalyst from the reaction mixture thesolvent and unreacted substrates were evaporated at a reduced pressure. The silylation product was extracted bymeans of pentane using a cannula system. The solvent was initially evaporated from the extract, and then the raw product waspurified on a SiO2-packedcolumn (modified with a 15% hexane solution of Et3N), using hexaneas eluent. The product was 0.721 g of4-(trimethylsilylethynyl)biphenyl, obtained with a yield of 96%.Analysiscalculated for C17H18Si C 81.54; H 7.25; found C 81.58; H7.27; 1H NMR (300 MHz, CDCl3,300 K) d(ppm) = 7.60 (d); 7.59(d); 7.57(m); 7.55 (s); 7.45(t); 7.37 (qt) ( 9H, Ph-C6H4-); 0.28(s, 9H, -SiMe3);13C NMR (75.46 MHz, C6D6,300 K) d(ppm) = 141.11; 140.25; 132.25;128.81; 127.61; 127.98; 126.83; 121.94; 104.93 (-C≡C-SiMe3);94.82 (-C≡C-SiMe3); -0.02 (-SiMe3).
94% With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine In toluene at 80℃; Inert atmosphere; 18 A reactor with a capacity of 40 mL, equipped with a magnetic stirrer was filled, under argon atmosphere, with 0.0085 g (0.015 mmol) of [{Ir(jt-Cl)(CO)2}2], and then with8 mL of anhydrous and deoxidized toluene and 0.7 g (5.4 mmol) of NEt(i-Pr)2. The whole mixture was stirred until the starting iridium(I) complex was dissolved, and then 0.535 g (3 mmol) of 4-ethynylbiphenyl and 0.96 g (4.8 mmol) of ISiMe3 were added to the resulting mixture. The reaction was carried out at a temperature of 80° C. until complete conversion of 4-ethynylbiphenyl. After the reaction was completed, in order to remove the catalyst from the reaction mixture the solvent was evaporated at a reduced pressure along with any residual unreacted substrates. The silylation product was extracted by means of pentane using a cannula system. The solvent was initially evaporated from the extract, and then raw product was purified on a Si02-packed column (modified with a 15% hexane solution of Et3N), using hexane as eluent. The product was 0.706 g of 4-(trimethylsilylethynyl)biphe- nyl, obtained with a yield of 94%.
  • 27
  • [ 29079-00-3 ]
  • [ 139215-43-3 ]
  • [ 1384868-80-7 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 60℃; for 6.16667h; Inert atmosphere;
  • 28
  • [ 29079-00-3 ]
  • [ 1359973-18-4 ]
  • [ 1397718-34-1 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 4-ethynyl-1,1'-biphenyl; 3-cyclopentyl-2-iodo-3H-imidazo[4,5-b]pyridine With tetrabutylammonium acetate In 1-methyl-pyrrolidin-2-one at 20℃; for 0.15h; Inert atmosphere; Stage #2: With (bis(tricyclohexyl)phosphine)palladium(II) dichloride In 1-methyl-pyrrolidin-2-one at 110℃; Inert atmosphere; Microwave irradiation; General procedure for coupling of 2-haloimidazo[4,5-b]pyridine derivative with different terminal acetylenes. (Sonogashira coupling) General procedure: To a solution of 3-substituted-2-haloimidazo[4,5-b]pyridine derivative (1 equiv) in NMP, were added terminal acetylene (1.5 equiv) and tetrabutyl ammonium acetate (1.5 equiv). The solution was purged with nitrogen and stirred at room temperature for 0.15 h, at that time PdCl2(PCy3)2 was added. The reaction solution was purged again with nitrogen and then placed in the microwave and heated for 10 to 30 min at 110 °C (for iodide and bromide intermediates). When chloro intermediate was used, the reaction contents were heated at 150 °C. When TLC and LCMS showed full consumption of starting materials, the reaction mixture was diluted with ethyl acetate, separated the ethyl acetate layer, given water wash, brine wash and was dried over anhydrous sodium sulphate and concentrated to get the crude material. The crude product was directly purified by column chromatography (0-15% hexane/EtOAc) to isolate the 3-alkyl-2-akynyl imidao[4,5-b]pyridine derivatives.
  • 29
  • [ 29079-00-3 ]
  • [ 1397718-38-5 ]
  • [ 1397718-34-1 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 4-ethynyl-1,1'-biphenyl; 2-chloro-3-cyclopentyl-3H-imidazo[4,5-b]pyridine With tetrabutylammonium acetate In 1-methyl-pyrrolidin-2-one at 20℃; for 0.15h; Inert atmosphere; Stage #2: With (bis(tricyclohexyl)phosphine)palladium(II) dichloride In 1-methyl-pyrrolidin-2-one at 150℃; Inert atmosphere; Microwave irradiation; General procedure for coupling of 2-haloimidazo[4,5-b]pyridine derivative with different terminal acetylenes. (Sonogashira coupling) General procedure: To a solution of 3-substituted-2-haloimidazo[4,5-b]pyridine derivative (1 equiv) in NMP, were added terminal acetylene (1.5 equiv) and tetrabutyl ammonium acetate (1.5 equiv). The solution was purged with nitrogen and stirred at room temperature for 0.15 h, at that time PdCl2(PCy3)2 was added. The reaction solution was purged again with nitrogen and then placed in the microwave and heated for 10 to 30 min at 110 °C (for iodide and bromide intermediates). When chloro intermediate was used, the reaction contents were heated at 150 °C. When TLC and LCMS showed full consumption of starting materials, the reaction mixture was diluted with ethyl acetate, separated the ethyl acetate layer, given water wash, brine wash and was dried over anhydrous sodium sulphate and concentrated to get the crude material. The crude product was directly purified by column chromatography (0-15% hexane/EtOAc) to isolate the 3-alkyl-2-akynyl imidao[4,5-b]pyridine derivatives.
  • 30
  • [ 69907-27-3 ]
  • [ 29079-00-3 ]
  • [ 1404454-62-1 ]
YieldReaction ConditionsOperation in experiment
84% With bis-triphenylphosphine-palladium(II) chloride; sodium acetate; lithium chloride In dimethyl amine at 120℃; for 25h; Inert atmosphere; regioselective reaction;
  • 31
  • 1,1,2,2-tetramethyl-1,2-bis(diphenylthiomethyl)disilane [ No CAS ]
  • [ 29079-00-3 ]
  • [ 1421425-87-7 ]
YieldReaction ConditionsOperation in experiment
64% With 1,1,3,3-tetramethylbutane isonitrile; palladium diacetate In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; 4.2 General procedure for the synthesis of bis(silylated) compounds 2 and 3 General procedure: To a toluene solution (10 mL) containing 1 (181 mg, 0.50 mmol), ethynylferrocene or 4-ethynylbiphenyl (0.70 mmol) and palladium acetate (2 mg, 0.01 mmol) was added 1,1,3,3-tetramethylbutylisocyanide (27.8 mg, 0.2 mmol). The yellow mixture quickly turned dark red after heating to 100 °C. Stirring was continued for 1 d, and then all volatiles were removed under reduced pressure. The residue was purified by column chromatography with CH2Cl2/n-hexane (1:9) as eluent affording 2 or 3 in 67 and 64% yield, respectively.
  • 32
  • [ 29079-00-3 ]
  • [ 92-92-2 ]
YieldReaction ConditionsOperation in experiment
87% With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry; Benzoic Acid (3a); Typical Procedure from Acetophenone or Phenylacetylene General procedure: To a mixture of acetophenone (100 mg, 1 equiv) or phenylacetylene (1 equiv) in dioxane (5 mL), Oxone (2 equiv) and TFA (2 equiv) were added. The mixture was then heated to reflux for 10 h and then cooled to r.t. H2O (10 mL) was added and the mixture was extracted with EtOAc (2 × 20 mL). The combined organic layers were treated with sat. NaHCO3 solution and the aqueous layer was poured onto crushed ice and treated with 2 M HCl; a colorless solid precipitated out. The precipitate was filtered off and dried in vacuo to give benzoic acid (3a) after column chromatography (silica gel; EtOAc-hexane, 1:9) as a white crystalline solid; yield: 0.096 g (95%) from 1a; mp 122-123 °C.
62% With carbon tetrabromide; water; oxygen In ethyl acetate for 40h; Irradiation;
  • 33
  • [ 29079-00-3 ]
  • [ 95-54-5 ]
  • [ 17286-67-8 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 4-ethynyl-1,1'-biphenyl With N-Bromosuccinimide In acetic acid for 2h; Inert atmosphere; Reflux; Stage #2: 1,2-diamino-benzene In acetic acid at 120℃; for 2h; Inert atmosphere; Quinoxalines 5 and 7; General Procedure General procedure: NBS (214 mg, 1.2 mmol) was added to a solution of the appropriate alkyne 4 (1.0 mmol) in AcOH (8 mL) at r.t. The reaction mixture was stirred at reflux for 2 h, then the respective diamine 2 (1.1 mmol) was added to the reaction mixture directly. The mixture was stirred at 120 °C for 2 h continuously, cooled to r.t., and the solvent was concentrated.The residue was diluted with aq NaHCO3 (95%, 10 mL) and the mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford the crude product. Purification on silica gel (hexanes/EtOAc: 10:1to 6:1) afforded quinoxaline 5 or 7.
79% With silver hexafluoroantimonate; 6-methoxyquinoline N-oxide; (triphenylphosphine)gold(I) chloride; bis(trifluoromethanesulfonyl)amide In toluene at 70℃; Sealed tube;
  • 34
  • [ 29079-00-3 ]
  • [ 92-91-1 ]
YieldReaction ConditionsOperation in experiment
97% With cobalt(III)((CH2NCHC6H4(O))2)(OAc); sulfuric acid In methanol; water at 80℃; for 20h; Schlenk technique;
97% With sulfuric acid; C18H15CoN2O10S2(2-)*2Na(1+); water In methanol at 80℃; for 20h; Schlenk technique; 2.2. General procedure for hydration of terminal alkynes General procedure: The 10 mL schlenk tube was charged with phenylacetylene (0.5 mmol, 51 mg), methanol (0.625 mL), catalyst (10 μmol, 2.0%), and then H2SO4 (10 μmol, 2.0%) dissolved in H2O (2.2mmol, 0.04 mL). The mixture was heated to 80 °C and at it for 20 h in a closed tube with a magnetic stirring bar. The progres sof the reaction was monitored using TLC and GC-MS. After the reaction, the mixture was cooled to room temperature, and CH2Cl2 (5 mL) and water (5 mL) were added to the mixture.The aqueous and organic layers were separated, and the aqueous phase was extracted with CH2Cl2 (5 mL 3). The combined organic extracts were washed with a saturated NaCl solution,dried over Na2SO4, and concentrated under reduced pressure. Then the product acetophenone was obtained.
95% With water at 60℃; for 20h; Sealed tube;
94% With silver tetrafluoroborate; water In acetic acid at 110℃; for 10h; regioselective reaction; 5 4.2. General procedure for the synthesis of methyl ketones (2a-x). 4.2.5. 1-([1,1'-Biphenyl]-4-yl)ethanone (2e) General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 mol%) was added. The mixture was stirred at 110°C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3×8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample. 4.2.5. 1-([1,1'-Biphenyl]-4-yl)ethanone (2e). 1H NMR (400 MHz, CDCl3): δ=8.02-8.05 (m, 2H), 7.67-7.70 (m, 2H), 7.61-7.64 (m, 2H), 7.45-7.49 (m, 2H), 7.38-7.42 (m, 1H), 2.64 (s, 3H). 13C NMR (100 MHz, CDCl3): δ=197.8, 145.7, 139.8, 135.8, 128.9, 128.9, 128.2, 127.2, 127.2, 26.6. MS (EI) m/z: 196, 181, 152, 76, 43.
93% With water at 80℃; for 15h;
90% With 3,4,5-trihydroxybenzoic acid; water at 60℃; for 6h; Sealed tube; Green chemistry;
86% With hydrogenchloride; water; copper(l) chloride In methanol at 20℃; for 6h; Irradiation; Inert atmosphere; Preparation of phenylacetylene General procedure: A 10 mL reaction vessel with a magnetic stirring bar was equipped with phenylacetylene (1 mmol), CuCl (1 mol%), HCl (0.2 mL, 37 wt %) and methanol (2 mL). The mixture was irradiated with a blue LED (5 W) and stirred under at r.t. in an air atmosphere for 6 h. The distance of the reaction vial from the light is about 2 centimeter. After the reaction, the solvent was removed under reduced pressure. Purification of the crude product was achieved by flash column chromatography using petrol ether/ethyl acetate (6:1~10:1) as eluent.
84% With formic acid; water; CoH6Mo6O24(3-)*3H3N*3H(1+)*7H2O at 60℃; for 1h; Green chemistry; chemoselective reaction;

  • 35
  • [ 29079-00-3 ]
  • [ 59612-56-5 ]
YieldReaction ConditionsOperation in experiment
90% With Oxone; potassium chloride In water; acetonitrile at 20℃; for 0.333333h;
88% With trichloroisocyanuric acid; p-methylphenylthiourea; water at 20℃; for 0.333333h; Sealed tube; Sonication; Green chemistry; chemoselective reaction; 4.1.1. General procedure for the synthesis of 2 General procedure: Procedure for 2: To a solution of alkyne (0.3 mmol) in water(1.5 mL) in sealed tube was added TXCA (0.3 mmol) and p-tolylthiourea (0.075 mmol, 12 mg), the reaction mixture was ultrasonic at room temperature under and the reaction was monitored by TLC. The reaction typically took 20 min. Upon completion, the mixturewas concentrated under reduced pressure.The residue was purified by column chromatography on silica gel(eluent: hexanes/ethyl acetate) to afford 2a - 2aa.
75% With sodium hydrogensulfate monohydrate; water; lithium chloride In acetonitrile at 20℃; for 24h; Schlenk technique;
  • 36
  • [ 29079-00-3 ]
  • [ 2920-38-9 ]
YieldReaction ConditionsOperation in experiment
72% With trimethylsilylazide; silver carbonate In dimethyl sulfoxide at 100℃; for 12h;
65% With N-chloro-succinimide; silver(I) nitrite In 1,4-dioxane at 20℃; for 8h; Sealed tube; 12 Example 12: Synthesis of 4-phenylbenzonitrile from 4-phenylphenylacetylene 4-phenylphenylacetylene 89 mg (0.50 mmol), silver nitrite 154 mg (1 mmol), N-chlorosuccinimide 133.5 mg (1 mmol)Add 10 mL of pressure-resistant sealed container in turn, and then add 5 mL of 1,4-dioxane.The mixture was stirred at room temperature, and the reaction was checked by TLC. The reaction was completed in 8 hours.The reaction solution was diluted with 10 mL of dichloromethane, and filtered to give a clear liquid.Separation by column chromatography (extraction of petroleum ether / ethyl acetate in a volume ratio of 30:1)Collecting eluate containing the objective product, the solvent was evaporated to give 4-phenyl-benzonitrile as a white solid 58.2mg (65% yield).
32% With tert.-butylnitrite; benzyl-methyl-amine In dimethyl sulfoxide at 110℃; for 12h;
  • 37
  • [ 13322-90-2 ]
  • [ 29079-00-3 ]
  • [ 1469874-78-9 ]
  • 38
  • [ 29079-00-3 ]
  • [ 2873-29-2 ]
  • [ 1469874-81-4 ]
YieldReaction ConditionsOperation in experiment
74% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20℃; for 0.0333333h; stereoselective reaction; Typical Procedure C-alkynylation of Glycals General procedure: To a mixture of glucal (1 equiv) and alkyne (1.2 equiv) in DCM at -20 °C, was added TMSOTf (50 mol %) and kept on stirring till completion of reaction as monitored on TLC. The reaction was quenched with sat. NaHCO3 solution and extracted with DCM (twice), washed with sat. brine and purified over silica gel (100-200 mesh) using hexane:EtOAc as eluent to afford pure products.
68% With copper(II) bis(trifluoromethanesulfonate); ascorbic acid In acetonitrile at 20℃; for 0.0333333h; diastereoselective reaction;
  • 39
  • [ 29079-00-3 ]
  • [ 6326-64-3 ]
  • [ 115720-41-7 ]
YieldReaction ConditionsOperation in experiment
With nickel(II) chloride hexahydrate; 2-(1-methyl-2-benzimidazole)-6-(1-(2,6-dimethylphenyl)iminoethyl)pyridine; zinc(II) iodide; zinc In acetonitrile at 20℃; for 4h; Schlenk technique; Overall yield = 88%;
  • 40
  • [ 29079-00-3 ]
  • [ 1528748-62-0 ]
  • [ 1528748-80-2 ]
YieldReaction ConditionsOperation in experiment
91% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; Synthesis of 2-(trifluoromethyl)phenothiazine-1,2,3-triazole hybrids 5a-v General procedure: Azide 3 (1.0mmol), alkynes 4a-4v (1.0mmol), copper sulfate.5H2O (20mol%) and sodium ascorbate (20mol%) in t-butanol & water (1:1, v/v, 4mL), was stirred at rt for 1-2h. After completion (TLC), the reaction mixture was diluted with ethyl acetate (20mL) and water (5mL), the organic layer was separated, washed with brine solution (2×10mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue thus obtained was purified over silica gel column chromatography eluted with ethyl acetate/ hexane (1:2) to give pure 1,2,3-triazole hybrids 5a-v.
  • 41
  • [ 121-43-7 ]
  • [ 29079-00-3 ]
  • [ 1415023-69-6 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4-ethynyl-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30 - 20℃; for 2h; Stage #3: With potassium hydrogenfluoride In tetrahydrofuran; hexane; water at -20 - 20℃; for 2h; General procedure for preparation of potassium alkynyltrifluoroborates (Scheme 2) General procedure: n-BuLi (4.70mL, 1.6M in hexane, 7.57mmol, 1.0equiv) was added dropwise to a solution of acetylene (7.57mmol, 1.0equiv) in 7.6mL of dry THF at -78°C under a nitrogen atmosphere. After 60min at this temperature, trimethylborate (1.10g, 11.3mmol, 1.5equiv) was added dropwise at -30°C. The mixture was stirred at this temperature for 60min and slowly allowed to warm to room temperature within another 60min. A saturated 4.5M aqueous solution of potassium hydrogen difluoride (KHF2) (10.1mL, 45.3mmol, 6.0equiv) was added at -20°C to the vigorously stirred solution. The resulting mixture was continued to stir for 60min at -20°C after which it was allowed to warm to room temperature for 60min. The solvent was removed under reduced pressure, and the resulting white solid was dried under high vacuum to remove water. The solid was washed first with acetone and then with hot acetone. The solution was concentrated to afford a white solid. The solid was dissolved in minimum amount of hot acetone, precipitated by adding methyl tert-butyl ether (MTBE), after which the solution was cooled to -20°C to complete precipitation of the solid. The product was collected as an off white solid 2a-o in 40-80% yield.
  • 42
  • [ 3296-06-8 ]
  • [ 29079-00-3 ]
  • [ 1599471-89-2 ]
YieldReaction ConditionsOperation in experiment
92% With Cu(at)PyIm-SBA-15 at 20℃; for 7h; synthesis of 1,4-disubstituted1,2,3-triazole General procedure: Aniline (0.5 g, 5.4 mmol) was placed into a 25 mL round bot-tomed flask which was then put in an ice water bath (0-5C).Subsequently, a mixture of conc. HCl-H2O (1.3 mL: 1.3 mL) wasadded to it and the mixture was stirred for 1 min. NaNO2(0.392 g,5.7 mmol), dissolved in 1 mL of water, was first cooled at 0-5Cand then added to the reaction mixture drop wise. After 2 min stir-ring, sodium azide (0.416 g, 6.4 mmol) was added and stirred for5 min. Then phenylacetylene (0.46 g, 4.6 mmol) and CuPyIm-SBA-15 (0.025 g, 0.1 mol%) were added to the reaction mixture followedby stirring at room temperature for 6 h (TLC). When the reactionwas over, the water layer was decanted off and the reaction mixturewas dissolved in ethanol. Then the catalyst was filtered througha sintered glass-bed (G-4), and washed with water (3 × 4 mL) fol-lowed by ethanol (3 × 3 mL) and acetone (2 × 4 mL). The productwas purified by a simple crystallization from ethanol to furnish thecorresponding triazole, 1,4-diphenyl-1H-[1,2,3]triazole, as a whitesolid (Yield = 98%),
  • 43
  • [ 29079-00-3 ]
  • [ 1516-58-1 ]
  • [ 1599471-90-5 ]
YieldReaction ConditionsOperation in experiment
93% With Cu(at)PyIm-SBA-15 at 20℃; for 7h; synthesis of 1,4-disubstituted1,2,3-triazole Aniline (0.5 g, 5.4 mmol) was placed into a 25 mL round bot-tomed flask which was then put in an ice water bath (0-5C).Subsequently, a mixture of conc. HCl-H2O (1.3 mL: 1.3 mL) wasadded to it and the mixture was stirred for 1 min. NaNO2(0.392 g,5.7 mmol), dissolved in 1 mL of water, was first cooled at 0-5Cand then added to the reaction mixture drop wise. After 2 min stir-ring, sodium azide (0.416 g, 6.4 mmol) was added and stirred for5 min. Then phenylacetylene (0.46 g, 4.6 mmol) and CuPyIm-SBA-15 (0.025 g, 0.1 mol%) were added to the reaction mixture followedby stirring at room temperature for 6 h (TLC). When the reactionwas over, the water layer was decanted off and the reaction mixturewas dissolved in ethanol. Then the catalyst was filtered througha sintered glass-bed (G-4), and washed with water (3 × 4 mL) fol-lowed by ethanol (3 × 3 mL) and acetone (2 × 4 mL). The productwas purified by a simple crystallization from ethanol to furnish thecorresponding triazole, 1,4-diphenyl-1H-[1,2,3]triazole, as a whitesolid (Yield = 98%),
  • 44
  • [ 29079-00-3 ]
  • [ 1864-94-4 ]
  • 3-([1,1'-biphenyl]-4-yl)-1-phenylprop-2-yn-1-one [ No CAS ]
  • 45
  • [ 29079-00-3 ]
  • [ 93131-78-3 ]
  • [ 1600531-62-1 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 4-methyl-2-oxo-2H-chromen-7-yl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate With (bis(tricyclohexyl)phosphine)palladium(II) dichloride In N,N-dimethyl acetamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-ethynyl-1,1'-biphenyl With tetrabutyl ammonium fluoride In N,N-dimethyl acetamide at 100℃; for 0.433333h; Inert atmosphere; Microwave irradiation; General procedure: A representative example of the nonaflate and 4-tolyl acetylene is taken. To asolution of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin (3b, 1 equiv) inDMA, were added PdCl2(PCy3)2 (5 mol %). The solution was purged withnitrogen and stirred at room temperature for 10 min, at which time 4-tolylacetylene (1.3 equiv) and TBAF3H2O (3 equiv) were added. The reactionsolution was purged again with nitrogen and then placed in the microwave andheated for 20-30 min at 100 C at 110 W. When TLC and LC-MS showed fullconsumption of starting materials, the reaction mixture was diluted with ethylacetate, separated the ethyl acetate layer, given water wash, brine wash andwas dried over anhydrous sodium sulfate and distilled under reduced pressureto get the crude material. The crude product was purified by columnchromatography (10-40% hexane/EtOAc) to isolate the 4-methyl-7-(2-ptolylethynyl)-2H-chromen-2-one (4e) in 88% yield.
  • 46
  • [ 29079-00-3 ]
  • [ 873-55-2 ]
  • [ 41024-57-1 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: sodium benzenesulfonate With hydrogenchloride In water at 20℃; for 0.0333333h; Stage #2: 4-ethynyl-1,1'-biphenyl With 2,6-dimethylpyridine In water at 20℃; for 1.33333h; Stage #3: sodium benzenesulfonate With 2,6-dimethylpyridine; hydrogenchloride In water at 20℃; for 8.5h;
70% With iron(III) chloride; dipotassium peroxodisulfate; oxygen In water at 20℃; for 8h; Green chemistry; General procedure for the one-pot synthesis of β-keto sulfones 3a-w General procedure: A mixture of alkyne 1 (0.25 mmol), sodium sulfinate 2 (0.375 mmol), FeCl3 (20 mol %),K2S2O8 (20 mol %), and water (3 mL) was stirred at rt in an open flask for 6-9 h(Table 2). After completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 5 mL). The combined organic phases were dried over anhyd. Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a mixture of EtOAc-n-hexane (1:4) as eluent to afford an analytically pure sample of β-keto sulfones 3 (Table 2).
67% With iron(III) chloride hexahydrate In water; isopropyl alcohol at 80℃; for 24h;
With iron(III) chloride; oxygen In methanol; water at 50℃; for 16h;
With [RuCl(mesitylene)(S,S)-4-((trimethoxysilyl)ethyl)phenylsulfonyl-1,2-diphenylethylenediamine]functionalized mesoporous SiO2-coated Fe3O4 nanoparticles; air In ethanol; water at 50℃;

  • 47
  • [ 29079-00-3 ]
  • [ 1620010-77-6 ]
  • [ 1620010-78-7 ]
YieldReaction ConditionsOperation in experiment
81% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; for 3h; 9 Preparation of Compound 1-231 After 1.08 g (2.97 mmol) of Compound SM and 641 mg (3.6 mmol) of 4-ethynylbiphenyl were dissolved in 22 ml of TEA, 28 mg (0.15 mmol) of CuI and 211 mg (0.3 mmol) of (Ph3P)2PdCl2 were added dropwise thereto. The mixture was stirred for 3 hours at 50°C. After the reaction completed, the result was extracted with ethyl acetate (EA) and water, and the EA layer was washed with 1N-HCl. The organic layer was dried using anhydrous sodium sulfate and filtered, and after the solvent was removed by vacuum distillation again, the result was separated and purified using column chromatography, and 1.1 g (81%) of target Compound 1-231 was obtained.
  • 48
  • [ 29079-00-3 ]
  • [ 1616562-53-8 ]
YieldReaction ConditionsOperation in experiment
88% With silver(I) azide; trimethylsilylazide; lithium hydroxide monohydrate In dimethyl sulfoxide at 80℃;
80% With trimethylsilylazide; lithium hydroxide monohydrate; anhydrous silver carbonate In dimethyl sulfoxide at 80℃; chemoselective reaction;
70% With trimethylsilylazide; anhydrous silver carbonate In lithium hydroxide monohydrate; dimethyl sulfoxide
With trimethylsilylazide; lithium hydroxide monohydrate; anhydrous silver carbonate In dimethyl sulfoxide at 80℃; stereoselective reaction;
With silver(I) azide; trimethylsilylazide; lithium hydroxide monohydrate In dimethyl sulfoxide at 80℃; Sealed tube;
With trimethylsilylazide; lithium hydroxide monohydrate; anhydrous silver carbonate In dimethyl sulfoxide at 80℃; III. General procedures for Synthesis of Viny Azides2. General procedure: To a solution of substrate (5 mmol), TMSN3 (0.98 ml, 7.5 mmol) and H2O (0.18 mL, 10 mmol) inDMSO (5 mL) at 80 oC was added Ag2CO3 (138 mg, 0.5 mmol). Then the mixture was stirred until (1-2 h)the complete consumption of substrate as indicated by TLC. The resulting mixture was concentrated andtaken up by dichloromethane (3 × 30 mL). The organic layer was washed with brine (3 × 40 mL), driedover MgSO4 and concentrated. The resulting crude materials were purified by flash columnchromatography (silica gel; hexane) to afford vinyl azides.
With trimethylsilylazide; lithium hydroxide monohydrate; anhydrous silver carbonate In dimethyl sulfoxide at 80℃;

  • 49
  • [ 138736-35-3 ]
  • [ 29079-00-3 ]
  • [ 1613216-93-5 ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; diisopropylamine In dichloromethane at 20℃; Synthesis of [bpyPt(C≡CC6H4Ph)2] (1) General procedure: A suspension of [bpyPtCl2] (70 mg, 166 mmol) in CH2Cl2 (10 mL), and diisopropylamine (3 mL) was degassed and CuI (10 mg, 0.060 mmol) and 4'-ethynylbiphenyl (73.8 mg, 414 mmol) were added to the reaction mixture, which was then stirred overnight at room temperature. The solvent was removed in vacuo, and the residue was purified by column chromatography packed with alumina using CH2Cl2 as eluent. The product was recrystallized by slow concentration of a CH2Cl2/hexane solution (0.055 g, 47 %) to give an orange crystalline solid.
  • 50
  • [ 766-99-4 ]
  • [ 71-43-2 ]
  • [ 29079-00-3 ]
  • 51
  • [ 29079-00-3 ]
  • [ 25015-63-8 ]
  • [ 941666-88-2 ]
YieldReaction ConditionsOperation in experiment
90% With lithium hexamethyldisilazane In toluene at 80℃; for 24h; Inert atmosphere; 5 Preparation method: Under the protection of nitrogen, add raw material 4-phenylphenylacetylene (0.5mmol), pinacol borane (0.6mmol), catalyst LHMDS (7mol%) and organic solvent toluene (0.5mL) into the reaction vessel and mix with stirring. After mixing uniformly, react at 80°C for 24h, filter and purify to obtain the product; the product separation yield is 90%.
79% With p-N,N-dimethylaminobenzoic acid In octane at 100℃; for 12h; Inert atmosphere;
77% With lithium hexamethyldisilazane In toluene at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;
54% With tropylium tetrafluoroborate In neat (no solvent) at 70℃; for 12h; Inert atmosphere;
With bis(pentafluorophenyl)borohydride In dichloromethane at 20℃; for 5h; Glovebox; Inert atmosphere; Sealed tube;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); carbon dioxide In toluene at 100℃; for 3h; Schlenk technique; Autoclave;

  • 52
  • [ 201230-82-2 ]
  • [ 29079-00-3 ]
  • [ 71-36-3 ]
  • butyl 2-(biphenyl-4-yl)acrylate [ No CAS ]
  • (Z)-dibutyl 2-(biphenyl-4-yl)maleate [ No CAS ]
  • dibutyl 2-(biphenyl-4-yl)succinate [ No CAS ]
  • (E)-3-([1,1'-biphenyl]-4-yl)acrylic acid n-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 33% 2: 25% 3: 9% With palladium(II) iodide In toluene at 100℃; for 24h; Autoclave; Catalytic hydrobutoxycarbonylation of phenylacetylene inthe presence of PdI2 General procedure: In a typical experiment, PdI2(9.7 mg, 0.027 mmol), phenylacety-lene (0.3 mL, 2.7 mmol), 1-butanol (2.46 mL, 27 mmol), and toluene(4 mL) were charged to the reactor. The autoclave was purged withCOwithCO at room temperature, pressurized to 10 bar with CO and heatedto 100C under stirring for 24 h. After conventional workup thequantitative product determination was carried out by GC-FIDanalyses and1H NMR spectroscopy.
  • 53
  • [ 434-45-7 ]
  • [ 29079-00-3 ]
  • 4-((1,1'-biphenyl)-4-yl)-1,1,1-trifluoro-2-phenylbut-3-yn-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With copper(II) oxide; sodium hydroxide In N,N-dimethyl acetamide at 50℃; for 24h; 5 2,2,2-Trifluoroacetophenone (0.5 mmol),4-phenylphenylacetylene (1.0 mmol),CuO (0.05 mmol),NaOH (0.1 mmol) and DMA (1 mL) were added to Xu Linke bottle,The reaction was stirred at 50 ° C for 24 hours and the reaction was followed by TLC.After the reaction was completed, the reaction was quenched by adding 15 mL of saturated brine and the reaction mixture was extracted with dichloromethane (15 mL × 3). The combined organic phases were concentrated using a rotary evaporator to give the crude product. The target product was obtained by column chromatography. The column The eluent used was petroleum ether: ethyl acetate (10: 1) and the product structure was identified by NMR and high resolution mass spectrometry. Isolated yield of 94%.
92% With copper diacetate; potassium carbonate In dimethyl sulfoxide at 50℃; for 24h;
85% With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 50 - 70℃; for 24h;
  • 54
  • [ 29079-00-3 ]
  • 3-(2-(azidomethyl)phenyl)-6,7-dimethoxy-2-methylquinazolin-4(3H)-one [ No CAS ]
  • 3-(2-((4-([1,1'-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-6,7-dimethoxy-2-methylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 0.5h; 6.5. General procedure for the synthesis of compounds (4a-r) General procedure: To a suspension of hetero aryl azide 9a-b (100 mg, 0.284 mol) and alkynes (0.284 mol) in THF: water (1:1) (10 mL), CuSO4.5H2O (5 mol%) and sodium ascorbate (10 mol%) were added. The reaction mixture was stirred at rt for 30 min. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The ethyl acetate extracts were combined, dried with Na2SO4 and evaporated to dryness under reduced pressure. The obtained crude product was purified by flash column chromatography over silica gel (5:95, methanol/ethyl acetate) to afford compounds 4a-r.
  • 56
  • [ 29079-00-3 ]
  • [ 1458630-33-5 ]
  • 1-(4-(4-([1,1'-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)butyl)-4-(2-methoxyphenyl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h; 19 General Method B To a suspension of CuI (0.2 equiv) in THF (10 mL) was addedthe appropriate azidobutylphenylpiperazine (1.0 equiv) andethynylaryl substrate (1.0 equiv). The reaction was stirred atroom temperature for 12 h before the resulting mixture wasconcentrated in vacuo and subjected directly to flash columnchromatography to afford the pure product. 6.1.19 1-(4-(4-([1,1'-Biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)butyl)-4-(2-methoxyphenyl)piperazine (BAK 05-18; 9e) Synthesized using General Method B in 82% yield (345 mg, 0.74 mmol) from azidobutylphenylpiperazine 7 (260 mg, 0.9 mmol) and 4-ethynyl-1,1'-biphenyl (160 mg, 0.9 mmol). 52 Mp 181-182 °C (oxalate salt). 1H NMR (400 MHz, CDCl3) δ 7.92-7.90 (m, 2H), 7.80 (s, 1H), 7.68-7.63 (m, 2H), 7.45 (t, J = 7.6 Hz, 2H), 7.38-7.34 (m, 1H), 7.01-6.84 (m, 4H), 4.47 (t, J = 7.2 Hz, 2H), 3.86 (s, 3H), 3.08 (br s, 4H), 2.63 (br s, 4H), 2.46 (t, J = 7.2 Hz, 2H), 2.07-2.0 (m, 2H), 1.65-1.57 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 152.22, 147.37, 141.25, 140.72, 140.49, 129.67, 128.83, 127.47, 127.43, 126.93, 126.05, 122.90, 120.95, 119.55, 118.14, 111.12, 57.72, 55.33, 53.43, 50.61, 50.27, 28.32, 23.79; Anal. (C29H33N5O·C2H2O4·1/2H2O) C, H, N.
  • 57
  • [ 29079-00-3 ]
  • 1-(4-azidobutyl)-4-(2,3-dichlorophenyl)piperazine [ No CAS ]
  • 1-(4-(4-([1,1'-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)butyl)-4-(2,3-dichlorophenyl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h; 25 General Method B To a suspension of CuI (0.2 equiv) in THF (10 mL) was addedthe appropriate azidobutylphenylpiperazine (1.0 equiv) andethynylaryl substrate (1.0 equiv). The reaction was stirred atroom temperature for 12 h before the resulting mixture wasconcentrated in vacuo and subjected directly to flash columnchromatography to afford the pure product. 6.1.25 1-(4-(4-([1,1'-Biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)butyl)-4-(2,3-dichlorophenyl)piperazine (BAK 05-23; 10e) Synthesized using General Method B in 78% yield (355 mg, 0.70 mmol) from azidobutylphenylpiperazine 8 (295 mg, 0.9 mmol) and 4-ethynyl-1,1'-biphenyl (160 mg, 0.9 mmol). Mp 196-197 °C (oxalate salt). 1H NMR (400 MHz, DMSO) δ 8.67 (s, 1H), 7.95 (d, J = 8.4 Hz, 2H), 7.78-7.71 (m, 4H), 7.48 (t, J = 8.0 Hz, 2H), 7.40-7.36 (m, 1H), 7.30-7.28 (m, 2H), 7.13-7.11 (m, 1H), 4.45 (t, J = 7.2 Hz, 2H), 2.97 (br s, 4H), 2.51 (br s, 4H), 2.38 (t, J = 6.8 Hz, 2H), 1.95-1.91 (m, 2H), 1.52-1.44 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 151.27, 147.54, 140.89, 140.60, 134.06, 129.73, 128.92, 127.59, 127.55, 127.04, 126.14, 124.65, 119.58, 118.67, 57.68, 53.35, 51.33, 50.37, 28.39, 23.85; Anal. (C28H29Cl2N5·C2H2O4) C, H, N.
  • 58
  • [ 29079-00-3 ]
  • 2-azido-N-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)acetamide [ No CAS ]
  • 2-(4-([1,1'-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)-N-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 1h; General procedure: Compound 3 (1.0 mmol), alkynes 4a-v (1.0 mmol), copper sulphate pentahydrate (20 mol%) and sodium ascorbate (20 mol%) in tert-butanol and water (1:1, v/v, 4mL) was stirred at RT for appropriate time. After completion of the reaction indicatedby TLC, the reaction mixture was treated with water (10 mL), extracted with ethyl acetate (2 x 20 mL) and the combined organic layer was washed with brine solution, dried over anhydrous sodium sulphate and concentrated underreduced pressure. The crude product was purified bycolumn chromatography over silica gel using ethyl acetate/hexane (1:2)to obtain corresponding 1,2,3-triazoles 5a-v in good yields.
  • 59
  • [ 29079-00-3 ]
  • 3-azidoquinuclidine [ No CAS ]
  • 3-(4-(biphenyl-4-yl)-1,2,3-triazol-1-yl)quinuclidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.95% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; 1.3 5-(1-(2-(Piperidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)-1H-indole (IND1): General procedure: i-(2-Azidoethyl)piperidine (0.0641 g, 0.42 mmol) from method A was reacted with 5-ethynyl-iH- indole (0.0499 g, 0.35 mmol) in a ito 1 ratio of t-BuOH and water with CuSO4*5H20 (0.0050 g, 0.02 mmol) and sodium ascorbate (0.0158 g, 0.08 mmol) as catalyst. The reaction was stirred at room temperature for 5 h. Afier that, the reaction mixture was extracted with CH2C12. The crude product was purified by column chromatography (EtOAc) to give a pale yellow solid compound (68.86%). FTIR (ATR) (cm’) 3318, 3148, 3083, 2924, 1480, 1469, 1452, 1438, 1346, 1225, 1121, 1054, 892, 795, 771, 745; ‘H-NMR (500 MHz, DMSO-d5) ö 8.41 (s, iH), 8.00 (dd, J=i.6, 0.8 Hz, iH), 7.58 (dd, J=8.4, 1.5 Hz, iH), 7.44 (d, J=8.4 Hz, iH), 7.36 (dd, J=2.9, 2.2 Hz, iH), 6.50-6.44 (m, iH), 4.48 (t, J=6.5 Hz, 2H), 2.76 (t, J=6.5 Hz, 2H), 2.47-2.34 (m, 4H), 1.48 (dt, J=iO.8, 5.6 Hz, 4H), 1.42-1.33 (m, 2H); ‘3C-NMR (126 MHz, DMSO-d5) ö 147.7, 135.6, 127.8, 126.0, 122.0, 120.3, 119.0, 116.7, 111.7, 101.4, 57.8, 53.8, 47.0, 25.5, 23.9; mp=i48-i49° C.; HRMS calculated (C17H21N5, MH)296.1871, found 296.1871.
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃;
  • 60
  • [ 29079-00-3 ]
  • [ 1554363-68-6 ]
  • (2R,3S,4R)-5-([1,1'-biphenyl]-4-ylethynyl)-2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyldiacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; General Procedure for theSonogashira coupling reaction: General procedure: Toa mixture of 2-iodo-3,4,6-tri-O-acetyl-D-glucal 1 (398 mg, 1 mmol) andDMF (5 mL) in a two neck round bottom flask under nitrogen was added palladiumacetate (11.2 mg, 5 mol%) and cesium carbonate (488.7 mg, 1.5 eq.). This wasthen followed by the dropwise addition of the terminal alkynes 2a-p (1.2 eq.) while stirring, at roomfor 0.3-5 hours. The color of the reaction mixture changes from a yellowish todark brown as the catalyst and base are added. After completion of reaction(TLC monitoring) concentrated aqueous solution of ammonium hydroxide (20 mL)was added to the reaction mixture and was extracted with ethyl acetate (3x25mL). The organic phase were combined and extracted with deionized/distilledwater (1x40 mL). The resulting organic phase was dried with magnesium sulfate,filtered and concentrated under vacuum. The product was purified by flashchromatography using ethyl acetate and hexane as eluents.
  • 61
  • [ 19437-26-4 ]
  • [ 29079-00-3 ]
  • C25H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With copper diacetate; triethylamine; In 1,4-dioxane; at 130℃; for 1h; A mixture of di-2-pyridinone(55 mg, 0.3 mmol), 4-biphenylacetylene (107 mg, 0.6 mmol), copper acetate (5.4Mg, 0.03 mmol), and triethylamine (60 mg, 0.6 mmol) were dissolved in 1,4-dioxane (2 mL). Get the resulting mixThe system was heated to 130 C and the TLC monitoring reaction was complete after 1 h reaction. Stop the reaction, filter, the crude product by silica gelColumn chromatography (100-200 mesh, n-hexane: ethyl acetate = 3: 1) to give the target product 100 mg in a yield of 92%.
  • 62
  • [ 29079-00-3 ]
  • [ 4559-70-0 ]
  • 1-([1,1'-biphenyl]-4-yl)-2-(diphenylphosphoryl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With oxygen; rhodamine B In isopropyl alcohol at 20℃; for 12h; Irradiation; regioselective reaction;
71% With water; oxygen; lithium hydroxide In N,N-dimethyl-formamide at 60℃; for 3h; β-Keto Phosphonate Derivatives 3a-w; General Procedure General procedure: alkyne 1 (0.25 mmol), H-phosphonate 2 (0.5 mmol), LiOH (0.05mmol), DMF (2 mL), and H2O (0.25 mL), and the mixture wasstirred at 60 °C for 3 h under O2 (balloon). When the reactionwas complete, it was quenched with aq NaHCO3 (20 mL) and themixture was extracted with EtOAc (3 × 10 mL). The combinedorganic layers were washed with sat. brine (×2) then dried(MgSO4), filtered, and concentrated in vacuum. The crudeproduct was purified by chromatography [silica gel, CH2Cl2-MeOH (30:1 to 50:1)].
  • 63
  • [ 29079-00-3 ]
  • [ 3815-20-1 ]
YieldReaction ConditionsOperation in experiment
69% With ammonia; dihydrogen peroxide; iodine In water; dimethyl sulfoxide at 20℃; for 3h; Irradiation;
  • 64
  • [ 880486-64-6 ]
  • [ 29079-00-3 ]
  • (3aR,5R,6S,6aR)-6-[4-(biphenyl-4-yl)-1H-1,2,3-triazol-1-yl]methyl}-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 24h; Synthesis of the triazoles 11a-m (General method) General procedure: A solution of CuSO4·5H2O (8 mg, 32 μmol, 0.1 equiv) inwater (0.5 ml) and a solution of sodium ascorbate (13 mg,65 μmol, 0.2 equiv) in water (0.5 ml) were addedsubsequently to a stirred solution of azide 914 (100 mg,0.32 mmol, 1 equiv) and terminal acetylene (0.48 mmol,1.5 equiv) in THF (5 ml). After reaction was complete(TLC control), solvent was evaporated under reduced pressure,the residue dissolved in EtOAc, washed with brine, driedover Na2SO4, and purified by column chromatographyeluting with eluent system hexanes-AcOEt, 1:1 to 1:3.
  • 65
  • [ 29079-00-3 ]
  • C42H68N3O10(1-)*Na(1+) [ No CAS ]
  • C56H78N3O10(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With copper(II) sulfate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; Inert atmosphere;
90% With copper(II) sulfate; sodium L-ascorbate In tetrahydrofuran at 20℃; Inert atmosphere; 2.2 (2) Synthesis of compound 5b To a solution of compound 4 (79.7 mg, 0.1 mmol) and 4-phenylphenylacetylene (26.1mg, 0.15 mmol) under argon,Intetrahydrofuran (3 mL) was rapidly added 0.38 mL of CuSO4 (1.0Maq) and 0.75 mLof sodium ascorbate (1.0 M aq), and the reaction was allowed to proceed at roomtemperature overnight. The organic phase was dried, filtered, and subjected tocolumn chromatography to give Compound 5b (87.8 mg, yield 90%), which waspurified by silica gel chromatography on silica gel eluting with ice- %).
  • 66
  • [ 29079-00-3 ]
  • (hydroxyimino){4-[2-(methylethyl)-6-phenylphenyl]-5-phenyl(1,2,4-triazol-3-yl)}methane [ No CAS ]
  • 3-{4-[2-(methylethyl)-6-phenylphenyl]-5-phenyl(1,2,4-triazol-3-yl)}-5-(4-phenylphenyl)isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium hypochlorite solution In tetrahydrofuran at 20℃; 3-{4-[2-(methylethyl)-6-phenylphenyl]-5-phenyl(1,2,4-triazol-3-yl)}-5-(4-phenylphenyl)isoxazole (15-h) To the solution of aldoxime 12-a (0.2 g, 0.523 mmol) and 4-ethynylbiphenyl (0.93 g, 10 eq.) in THF (8 mL) was added bleach (6.15 %, 5 eq.) slowly at rt. The reaction mixture was stirred at rt for 2 hrs. Then the mixture was treated with ethyl acetate (30 mL) and water (20 mL). The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. By column chromatography (10-40 % ethyl acetate in hexane) 0.209 g of product 15-h was obtained as a solid (72 % yield). mp: 232 oC, LC/MS: m/z 559.3 (M++1), 1H NMR (500 MHz, CD2Cl2): δ 7.89 (d, 2H, J = 6.7 Hz), 7.75 (d, 2H, J = 7.6 Hz), 7.70-7.67 (m, 3H), 7.56-7.55(m, 1H), 7.51-7.48 (m, 2H), 7.44-7.43 (m, 4H), 7.35-7.29 (m, 3H), 7.18-7.15 (m, 1H), 7.09-7.06 (m, 2H), 7.03 (s, 1H), 6.80-6.79 (m, 2H), 2.59 (sep, 1H, J = 6.7 Hz), 1.04 (d, 3H, J = 6.7 Hz), 0.93 (d, 3H, J = 6.7 Hz). 13C NMR (125 MHz, CD2Cl2): δ 169.70, 155.25, 153.48, 147.13, 146.02, 143.23, 139.89, 139.79, 137.95, 130.68, 130.62, 129.97, 128.92, 128.89, 128.43, 128.20, 128.00, 127.69, 127.63, 127.38, 126.99, 126.69, 126.66, 126.31, 125.51, 99.39, 28.39, 23.27, 22.76.
  • 67
  • [ 29079-00-3 ]
  • [ 1315179-54-4 ]
  • 2-([1,1′-biphenyl]-4-yl)-5-phenylpyrazolo[1,2-a][1,2,3]triazol-8-ium-1-ide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; Bis<2-(N,N-dimethylamino)aethyl>aether; triethylamine In tetrahydrofuran at 20℃; for 2.5h; Synthesis of 4b as a Typical Procedure of the Click Reaction (Method A) General procedure: To a solution of azidoditriflate 2a(36.5 mg, 0.092 mmol) in THF (9.0 mL) were added the ligand-copper solution (0.46 mL, 0.01 Msolution in THF), Et3N (65 µL, 0.46 mmol), and alkyne 3b(12 µL, 0.14 mmol) at room temperature, successively. The mixture was stirred at room temperature for 2.5 h and concentrated under reduced pressure.
  • 68
  • [ 29079-00-3 ]
  • benzyl 1-ethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]
  • (S)-benzyl 1-([1,1’-biphenyl]-4-ylethynyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With water; 2,6-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine; copper(I) bromide; ytterbium(III) triflate In toluene at 20℃; enantioselective reaction; Alkynylated N-Acyl Hemiaminals 6 and 8; General Procedure General procedure: A mixture of CuBr (0.01 mmol, 0.1 equiv) and L1 (0.012 mmol, 0.12equiv) in toluene (1.0 mL) was stirred for 1 h at r.t., before 5a or 7 (0.1mmol, 1.0 equiv), phenylacetylene (2) (0.2 mmol, 2.0 equiv), and H2O(0.2 mmol, 2.0 equiv) were added successively. The mixture was cooled to 0 °C and Yb(OTf)3 (0.1 mmol, 1.0 equiv) was added. After stirring for 12 h, a further quantity of a mixture of CuBr (0.005 mmol,0.05 equiv) and L1 (0.006 mmol, 0.06 equiv) in toluene (0.3 mL) was added, followed by 2 (0.1 mmol, 1.0 equiv) and Yb(OTf)3 (0.05 mmol,0.5 equiv). The resulting mixture was allowed to stir for 48-72 h at 0 °C before the solvent was removed. The residue was purified by flash chromatography on silica gel saturated with Et3N (EtOAc-PE,2:98) to afford product 6 or 8.
  • 69
  • [ 29079-00-3 ]
  • [ 775-12-2 ]
  • diphenyl(1-(4-(1,1’-biphenyl))vinyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 4-ethynyl-1,1'-biphenyl; diphenylsilane With [(S)-tBu-Pybox]CoCl2 In tetrahydrofuran at -35℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With sodium triethylborohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique; regioselective reaction;
67% With sodium t-butanolate In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; 24 Preparation and characterization of diphenyl(1-(4-(1,1’-biphenyl))vinyl)silane: Under an argon atmosphere, add 20 mg of heterogeneous catalyst, 1.0 mmol of 4-ethynyl-1,1-biphenyl, 1.2 mmol of diphenylsilane, and 3.0 mL of tetrahydrofuran to a 25 mL branch tube with a magnetic stir bar Then, 40 mg of sodium tert-butoxide was added, and the reaction was stirred at room temperature for 4 hours. The solvent was removed in vacuo. The crude product was purified by column chromatography using petroleum ether as the eluent to obtain a colorless liquid product with a yield of 67%.
52% With C22H28N2; cobalt(II) acetate In tetrahydrofuran at 40℃; for 10h; Schlenk technique; Glovebox;
With C25H25Br2CoN3O; sodium triethylborohydride In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; regioselective reaction;

  • 70
  • [ 815-03-2 ]
  • [ 29079-00-3 ]
  • 5-([1,1'-biphenyl]-4-yl)-4-iodo-3-(trifluoromethyl)isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With N-iodo-succinimide; sodium hydrogencarbonate In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; II. General Procedure for the Synthesis of TrifluoromethyliodoisoxazoleCompounds (4a-4t) General procedure: To a dry reaction tube, 2a (147 mg, 1.0 mmol), Alkyne (2.0 equiv), NaHCO3 (101 mg,1.2 mmol), NIS (450 mg, 2.0 mmol) and CH2Cl2 (6 mL) was added successively atroom temperature under N2 atmosphere. Then the reaction was stirred at roomtemperature. By the end (monitored by 19F NMR), the system was diluted with water,and extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried(MgSO4), concentrated under reduced pressure. The residue was purified by columnchromatography (0% →30% ethyl acetate in hexane) affording the desirable product.
  • 71
  • [ 29079-00-3 ]
  • [ 1066-54-2 ]
  • [1,1'-biphenyl]-4-yl(buta-1,3-diyn-1-yl)trimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(l) chloride In acetone at 25℃; Synthesis of alkyne substrates In a 25 mL round-bottomed flask, were added CuCl (39.2 mg, 0.4 mmol, 20 mol%), and tetramethylethylenediamine (TMEDA, 6.97 mg, 0.06 mmol, 3 mol%) in acetone (5 mL). The mixture was stirred and simultaneously bubbled with a stream of O2 for 30 min. Then a mixture of S1a (356 mg, 2 mmol) and trimethylsilylacetylene S2a (196.0 mg, 2 mmol) in anhydrous acetone (8 mL) was added. The reaction was carried out overnight at 25° C. After the reaction, the mixture was poured over and filtered through a silica gel pad under vacuum. The filtrate was added with CH2Cl2 (15 mL) and washed with water (15 mL × 3) and saturated brine (15 mL × 3). The organic layer was separated and dried over Na2SO4. After filtration and evaporation, the resulting crude product was purified by column chromatography with petrol ether as eluent to afford S3a (334.3 mg, 61%).
With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(l) chloride In acetone at 20℃;
  • 72
  • [ 124-38-9 ]
  • [ 29079-00-3 ]
  • [ 28188-41-2 ]
  • 3-cyanobenzyl 3-([1,1'-biphenyl]-4-yl)propiolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With caesium carbonate; silver(I) iodide In acetonitrile at 40℃; for 48h; Schlenk technique; 4.2. General procedure of Ag (I)-catalyzed carboxylation General procedure: In a typical procedure, a 50 mL Schlenk tube was charged withalkyne 1 (1.0 mmol), benzyl halide 2 (1.1 mmol), AgI (0.02 mmol),Cs2CO3 (1.5 mmol) and anhydrous CH3CN (5 mL). CO2 (99.999%,balloon) were then introduced into the reaction mixture understirring. After stirring at 40 C for 48 h, the reaction mixture wascooled to room temperature, ltered and evaporated in vacuo. Theresulting residue was then puried by column chromatography onsilica gel (eluent: petroleum ether: ethyl acetate 20:1) to affordthe corresponding products 3aa-3aq.
  • 73
  • [ 29079-00-3 ]
  • (R)-(2-azidophenyl)(3-hydroxypyrrolidin-1-yl)methanone [ No CAS ]
  • (R)-(2-(4-([1,10-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)phenyl)(3-hydroxypyrrolidin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 50 - 60℃; for 6h; General procedure for Triazoles synthesis General procedure: In a t-BuOH/H2O (6 mL, 1:1) solution (R)-(3-azidopyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone (10) (685 mg, 1.680mmol),cyclopropylalkyne (1.680 mmol), copper(II) sulfate (21 mg,0.080 mmol) and sodium ascorbate (33.4 mg, 0.170 mmol) wereadded with vigorous stirring at 50-60 C for 6 h. Water (15 mL)was added to the reaction mixture and then extracted with ethylacetate (3 25 mL). The extracts were combined and dried overanhydrous Na2SO4. After the evaporation of the solvent, the residuewas purified by flash chromatography to obtain (R)-(3-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone (11) as a semi-solid (70% yield).
  • 74
  • [ 29079-00-3 ]
  • [ 75-86-5 ]
  • (E)-3-([1,1‘-biphenyl]-4-yl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With 1,1'-bis-(diphenylphosphino)ferrocene; (hydridotris(1-pyrazolyl)borato)(1,5-cyclooctadiene)rhodium(I) In acetonitrile at 110℃; for 12h; Inert atmosphere; Glovebox; Sealed tube; stereoselective reaction;
69% With 1,1'-bis-(diphenylphosphino)ferrocene; (hydridotris(1-pyrazolyl)borato)(1,5-cyclooctadiene)rhodium(I) In acetonitrile at 110℃; for 12h; Inert atmosphere; Glovebox; Sealed tube; stereoselective reaction; (E)-3-([1,1‘-biphenyl]-4-yl)acrylonitrile (2c) In an anhydrous, argon-filled glovebox, a 4 ml. vial was charged with TpRh(COD) (6.3 mg, 15 mol, 7.5 mol%), dppf (8.3 mg, 15 mol, 7.5 mol%), and MeCN (1 .5 ml_, c = 0.13 M). 4-Ethynyl-1,1'-biphenyl (35.8 mg, 0.200 mmol, 1 .00 equiv) and acetone cyanohydrin (20.4 mg, 23.5 μΙ_, 0.240 mmol, 1 .20 equiv) were then added to the reaction mixture. The vial was sealed with a Teflon cap and moved from the glovebox to a preheated metal heating block (1 10 °C). The reaction mixture was then stirred at 1 10 °C for 12 hours. After cooling to 23 °C, the resulting mixture was filtered through a short plug of silica gel, eluting with EtOAc. The filtrate was collected and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel, eluting with EtOAc/hexane 1 :10 (v/v) to afford 28.3 mg (69%) of the title compound as yellow solid. Rf = 0.40 (EtOAc/hexanes 1 :10 (v/v)).NMR Spectroscopy:1H NMR (500 MHz, CDCI3, 23 °C, δ): 7.65 - 7.60 (m, 4H), 7.54 - 7.52 (m, 2H), 7.48 - 7.46 (m, 2H), 7.44 (d, J = 16.5 Hz, 1 H), 7.41 - 7.38 (m, 1 H), 5.91 (d, J = 16.5 Hz, 1 H).13C NMR (125 MHz, CDCI3, 23 °C, δ): 150.2, 144.2, 139.9, 132.6, 129.1 , 128.3, 128.0, 127.9, 127.2, 1 18.4, 96.2.HRMS-FIA (m/z): calc'd for C15H11 N [M]+, 205.0888; found: 205.0886.
  • 75
  • [ 29079-00-3 ]
  • [ 132922-37-3 ]
  • 4-([1,1'-biphenyl]-4-yl)-1-(1H-indol-3-yl)but-3-yn-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% Stage #1: 4-ethynyl-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide In tetrahydrofuran; hexane at -78 - 0℃; for 1.08333h; Inert atmosphere;
Stage #1: 4-ethynyl-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide In tetrahydrofuran; hexane at -78 - 0℃; for 1.08333h; Inert atmosphere;
  • 76
  • [ 566205-01-4 ]
  • [ 29079-00-3 ]
  • 3-(biphenyl-4-ylethynyl)-5-bromo-6-chloropyrazin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere; General procedure: To a stirred solution of 3,5-dibromo-6-chloro-pyrazin-2-amine (3.0 g, 10.56 mmol) in anhydrous THF (60 mL) under nitrogen atmosphere, TEA (3.2 mL, 30 mmol), Pd(PPh3)2Cl2 (0.74 g, 1.0 mmol), CuI (0.2 g, 1.0 mmol) and phenyl acetylene (1.07 mL, 10 mmol) were added subsequently and stirred for 3 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was concentrated in vacuum dried over anhydrous MgSO4, then purified by silica gel column chromatography (7% EA/hexane) to afford the desired compound.
  • 77
  • [ 593-60-2 ]
  • [ 29079-00-3 ]
  • 4-(but-3-en-1-yn-1-yl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 24℃; for 13h; Inert atmosphere; Alkaline conditions;
96% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 24℃; for 13h; Inert atmosphere;
71% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at -10 - 20℃; for 20h; Inert atmosphere;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Glovebox;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Sealed tube; Inert atmosphere;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 20℃; Inert atmosphere;
Stage #1: Vinyl bromide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-ethynyl-1,1'-biphenyl In tetrahydrofuran at 20℃; Inert atmosphere;

  • 78
  • [ 29079-00-3 ]
  • [ 6630-33-7 ]
  • [ 1017235-21-0 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere; Schlenk technique; Stage #2: 4-biphenylylacetylene In tetrahydrofuran for 3h; Schlenk technique; Inert atmosphere; Reflux;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; for 8h; Inert atmosphere;
With copper (I) iodide; bis (triortho-tolylphosphine)palladium(II) chloride In triethylamine at 50℃; for 12h; Inert atmosphere; 4.2. Typical procedure for preparation of N-(o-arylethynyl)benzylp-toluenesuldonamide 1 General procedure: To a solution of o-bromobenzaldehyde (10.0 mmol, 1.85 g),PdCl2(PPh3)2 (0.2 mmol, 140.4 mg) and CuI (0.1 mmol, 19.0 mg) inEt3N (0.3 M) was added ethynylbenzene (12.0 mmol, 1.32 mL). Theobtained mixture was stirred for 12 h at 50C under argon atmosphere.Sat. aq. NH4Cl solution (15.0 mL) was added to the mixture, and the product was extracted with CHCl3 (15.0 mL 3). Theorganic layer was dried over Na2SO4 and filtered. After removal ofthe solvent under reduced pressure, the residue was purified bysilica-gel column chromatography (eluent: n-hexane:EtOAc 19:1)to give o-(phenylethynyl)benzaldehyde (1.96 g, 95%). To a solutionof o-(phenylethynyl)benzaldehyde in EtOH (1.0 M) was added hydroxylaminehydrochloride (1.2 equiv.). The mixture was stirred for1 h at room temperature. To the obtained mixture were slowlyadded Zn powder (2.5 equiv.) and hydrochloric acid (12.0 M, 4.0equiv.) at 0 C. The obtained mixture was stirred for 0.5 h at roomtemperature under argon atmosphere. A solution of ammonia(28e30%) was slowly added until pH S 7, and the product wasextracted with CHCl3 (15.0 mL 3). The organic layer was driedover Na2SO4 and filtered. After removal of the solvent underreduced pressure, p-toluenesulfonyl chloride (1.1 equiv.) and pyridine(0.5 M) were added to the residue in dichloromethane (1.0 M)at 0 C. The obtained mixture was stirred for 12 h at room temperatureunder argon atmosphere. Aq. NH4Cl solution (15.0 mL)was added to the mixture, and the product was extracted withCHCl3 (15.0 mL 3). Then, the organic layer was dried over Na2SO4and filtered. After removal of the solvent under reduced pressure,the residue was purified by silica-gel column chromatography(eluent: n-hexane:EtOAc 3:1) to give N-(o-phenylethynyl)benzylp-toluenesulfonamide 1A (2.76 g, 76%). Other N-(o-arylethynyl)benzyl p-toluenesulfonamides 1Be1W were obtained in 55%e78%yields by the same procedure.
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 70℃; Inert atmosphere;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 55℃; Inert atmosphere; 2.1 General procedures for the synthesis of substrates General procedure: To a solution of 2-bromobenzaldehyde (1.85 g, 10.0 mmol) and ethynylbenzene (1.124g,11.0 mmol) in Et3N (20.0 mL) was added Pd(PPh3)2Cl2 (140 mg, 2.0% mol) and CuI (20 mg,1.0% mol). The mixture was stirred at 55 oC for overnight. It was then quenched with water andwashed with ethyl acetate. After removal of solvent, the crude residue was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate = 100:1, v/v) to afford the desiredproduct 2-(phenylethynyl)benzaldehyde (2.02 g, 98% yield).

  • 79
  • [ 29079-00-3 ]
  • [ 71559-15-4 ]
YieldReaction ConditionsOperation in experiment
85% With dipotassium peroxodisulfate; trimethylsilylazide; oxygen; copper diacetate In dimethyl sulfoxide at 20 - 25℃; for 12h; 4 Synthesis of 2-azido-1- (4-biphenylyl) ethanone At room temperature, copper acetate (5 mol%),Potassium persulfate (0.8 mmol, 2 equiv) was added to the reaction tube,And then pumping - filling oxygen, and replaced three times, in the oxygen environment,The reaction solvent 2mLDMSO was added,4-ethynylbiphenyl (0.4 mmol, 1 equiv),Trimethylsilyl azide (1.2 mmol, 3 equiv),And stirred at a reaction temperature of 25 ° C for 12 h.After completion of the reaction by thin layer chromatography, 20 mL of water and 10 mL of ethyl acetate extraction were added,Then dried over anhydrous sodium sulfate, filtered after 5 minutes,The filter cake was washed with ethyl acetate (5 mL x 3 times) and then the solvent was removed,The product was isolated by column chromatography (eluent: petroleum ether: ether = 100: 1)The product was a white solid with 85% yield;
  • 81
  • [ 910209-21-1 ]
  • [ 29079-00-3 ]
  • C17H17NO2S [ No CAS ]
  • 82
  • [ 29079-00-3 ]
  • (E)-4,4''-(but-1-en-3-yne-1,4-diyl)di-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With [{Pd(μ-OH)Cl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)}2]; potassium hydroxide In ethanol at 22℃; for 24h; Inert atmosphere; Schlenk technique; stereoselective reaction; 4.3. General procedure for the synthesis of 1,4-bis(aryl)but-1-en-3-ynes in ethanol General procedure: Glass reactor (3 mL) equipped with a condenser and a stirringbar was charged under argon with arylacetylene (9.11 104 mol),EtOH (99.8%) (2 mL) and catalyst 8 (0.25-2.0 mol% in relation toacetylene). The reaction mixture was stirred at 22 °C for 24 h. Thenthe solventwas evaporated under reduced pressure and the residuewas purified by column chromatography (silica gel, hexane/CH2Cl2 = 4/1). Evaporation of the solvent gave an analytically pureproduct.
95% With C77H74N2O3PtSi2 In toluene at 60℃; Inert atmosphere; diastereoselective reaction;
  • 83
  • [ 29079-00-3 ]
  • [ 66003-78-9 ]
  • [ 15784-39-1 ]
  • 84
  • [ 29079-00-3 ]
  • [copper(III)(1,10-phenanthroline)(CF3)3] [ No CAS ]
  • (Z)-4-(1,3,3,3-tetrafluoroprop-1-en-1-yl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With cesium fluoride In N,N-dimethyl-formamide at 100℃; for 6h; Schlenk technique; Inert atmosphere; stereoselective reaction;
69% With cesium fluoride In N,N-dimethyl acetamide at 110℃; for 15h; Inert atmosphere; 5 A method of preparing a fluorine-containing styrene compound using the following process steps: Copper trifluoromethyl compound (0.10 mmol, 45 mg), cesium fluoride (0.5 mmol, 75 mg) and biphenylacetylene (2e, 0.1 mmol, 18 mg) were placed in a 25 mL reaction tube, vacuumed and filled with nitrogen (three times). DMA (2 mL) was injected with a syringe under a nitrogen atmosphere.After stirring for 15 h in an oil bath at 110 ° C, the temperature was cooled to room temperature, and 20 mL of water was added to the reaction system, followed by extraction with 25 mL of ethyl acetate.The base layer was washed with saturated brine and dried over Na 2 SO 4 .Add a small amount of silica gel to spin column chromatography.The product was obtained as a white solid 3e (yield 69%).
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