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[ CAS No. 2789-89-1 ] {[proInfo.proName]}

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Chemical Structure| 2789-89-1
Chemical Structure| 2789-89-1
Structure of 2789-89-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2789-89-1 ]

CAS No. :2789-89-1 MDL No. :MFCD00185147
Formula : C14H8Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :FJQGIJIHOXZMMJ-UHFFFAOYSA-N
M.W : 336.02 Pubchem ID :3464242
Synonyms :

Calculated chemistry of [ 2789-89-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 74.26
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.62
Log Po/w (XLOGP3) : 5.32
Log Po/w (WLOGP) : 4.69
Log Po/w (MLOGP) : 5.62
Log Po/w (SILICOS-IT) : 5.24
Consensus Log Po/w : 4.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.83
Solubility : 0.000497 mg/ml ; 0.00000148 mol/l
Class : Moderately soluble
Log S (Ali) : -5.07
Solubility : 0.00285 mg/ml ; 0.00000848 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.67
Solubility : 0.0000717 mg/ml ; 0.000000213 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 2789-89-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P271-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P391-P403+P233-P405-P501 UN#:3077
Hazard Statements:H315-H318-H335-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2789-89-1 ]

* 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 [ 2789-89-1 ]

[ 2789-89-1 ] Synthesis Path-Downstream   1~79

  • 1
  • [ 49764-92-3 ]
  • [ 2789-89-1 ]
  • [ 19057-50-2 ]
  • 2
  • [ 2789-89-1 ]
  • [ 33513-42-7 ]
  • [ 84907-55-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium Yield given. Multistep reaction;
  • 3
  • [ 2789-89-1 ]
  • [ 35578-47-3 ]
YieldReaction ConditionsOperation in experiment
65% With iodine; In dimethyl sulfoxide; at 155℃; for 6h; A solution of bis(4-bromophenyl)acetylene (1.500 g, 4.46 mmol, 1 equiv), and iodine(566 mg, 2.23 mmol, 0.5 equiv) in DMSO (7.5 mL) was stirred at 155 00 for 6 h. Thereaction mixture was then cooled down to room temperature and a 1% aqueoussolution of Na2S2O4 (100 mL) was added. The resulting yellow crystals were filtratedand washed with water. Recrystallisation from dioxane afforded 101 as yellow crystals(1.06 g, 65%).
  • 4
  • [ 2789-89-1 ]
  • [ 479-33-4 ]
  • [ 22932-53-2 ]
YieldReaction ConditionsOperation in experiment
100% In diphenylether at 260 - 270℃; for 69h; 1.a Synthesis route a) 1 ,2-bis(4-bromophenyl)-3,4,5,6-tetraphenylbenzene Synthesis route a) 1 ,2-bis(4-bromophenyl)-3,4,5,6-tetraphenylbenzene A mixture of tetraphenylcydopentadienone (5.0 mmol), and bis(p-promophenyl) acetylene (5.0 mmol) in diphenyl ether (20 ml) was heated to 260 °C overnight. Then the temperature was raised to 270 °C. After 69 h, the reaction mixture was cooled, and methanol (100 ml) was added. After stirring for 1 h, the product was filtered off, washed with methanol, and finally dried in vaccuo overnight. Yield: Quantitative.
85% In various solvent(s) at 305℃; for 1h;
45% In diphenylether at 220℃; for 12h; Microwave irradiation;
  • 5
  • [ 2789-89-1 ]
  • [ 35578-47-3 ]
  • (Z)-1,2,3,4-Tetrakis-(4-bromo-phenyl)-but-2-ene-1,4-dione [ No CAS ]
  • 6
  • [ 23773-30-0 ]
  • [ 2789-89-1 ]
YieldReaction ConditionsOperation in experiment
97% With [PhC≡W{OC(CF3)Me2}3] In toluene at 25℃; for 2h; Inert atmosphere; Molecular sieve; Glovebox; General procedure for self-metathesis. General procedure: Under an argon atmosphere, a flask was charged with the substrate (0.5 mmol), molecular sieves 5 Å (500 mg) and toluene (internal alkynes: 2.5 mL, terminal alkynes: 24 mL). Then the catalyst (0.5 mol % W2F3, 1 mol % WPhF3) was added and the mixture was stirred for 2 h at room temperature. The catalyst and the molecular sieves were removed by filtration through alumina and the solvent was evaporated. The crude reaction product was purified by flash chromatography on silica gel with ethyl acetate-hexane (1:8).
36% In various solvent(s) at 140℃;
With p-OMe-C6H4C≡Mo(1,3-dimethylimidazol-2-ylidene)(OCMe(CF3)2)3 In toluene at 20℃; for 3h; Molecular sieve; Inert atmosphere; Glovebox;
96 %Chromat. With (p-OMe-C6H4C≡)Mo(OCMe(CF3)2)3-(1,3-di(isopropyl)imidazol-2-ylidene)complex on silica650 In toluene at 20℃; for 4h; Molecular sieve; Inert atmosphere; Schlenk technique; Glovebox;

  • 7
  • [ 2789-89-1 ]
  • [ 13321-74-9 ]
  • 1,2-bis(2',5'-dimethoxy-4'-methylbiphenyl-4-yl)acetylene [ No CAS ]
  • 8
  • [ 2789-89-1 ]
  • [ 89343-06-6 ]
  • [ 325834-47-7 ]
YieldReaction ConditionsOperation in experiment
95% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 16h; Heating;
94% With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; diisopropylamine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
74% With copper(l) iodide; triethylamine; triphenylphosphine In toluene at 80℃; for 5h;
  • 9
  • [ 2789-89-1 ]
  • [ 1066-54-2 ]
  • 1,2-bis(4-((trimethylsilyl)ethynyl)phenyl)ethyne [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With piperidine; copper(l) iodide; triphenylphosphine In various solvent(s) at 80℃; for 5h;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 40℃; for 24h; Sealed tube; Inert atmosphere; To a 50 mL test tube was added the crude product from above, Pd(PPh3)4 (0.057 g, 0.05 mmol), and CuI(0.019 g, 0.10 mmol). To a separate test tube was added trimethylsilylacetylene (0.325mL, 0.226g, 2.3mmol), tetrahydrofuran (20 mL), and triethylamine (5 mL). Each tube was sealed with a rubber septum andpurged with a continuous stream of argon (5 min). The contents of the liquids tube were transferred to thesolids tube via cannula under argon. The resulting mixture was stirred at 40C under argon for 24 h. Theresulting suspension was extracted between dichloromethane and 5% NH4OH (aq). The organic layer wasseparated and dried over MgSO4. After filtration to remove the drying agent, the solvent was removed viarotary evaporation to give a brown-orange powder. 1H NMR spectrum matched that previously described.This crude 4,4’-bis[(trimethylsilyl)ethynyl]tolane product was used directly in the next step without further purification.
  • 10
  • [ 589-87-7 ]
  • [ 1066-54-2 ]
  • [ 2789-89-1 ]
YieldReaction ConditionsOperation in experiment
96% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃; for 4h;
93% With palladium; potassium carbonate In ethanol; water at 40℃; for 0.833333h;
89% With copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 20℃; for 18h;
85% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetonitrile at 50℃; for 48h; Inert atmosphere;
81% Stage #1: 1,4-bromoiodobenzene; trimethylsilylacetylene With potassium carbonate In methanol; acetonitrile at 40℃; Stage #2: 1,4-bromoiodobenzene In methanol; acetonitrile at 40℃; chemoselective reaction; 2.2 General procedure for synthesis of diarylacetylenes General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40°C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI.
63% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; benzene at 20℃; Inert atmosphere; Darkness;
60% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 18h; Inert atmosphere;
60% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; Inert atmosphere; Darkness;
57% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 120℃; Microwave irradiation;
38% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60℃; for 18h; Inert atmosphere;
34% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 20℃; for 18h; Inert atmosphere; 1 Example 1 Under a nitrogen atmosphere,A 5 ml (17.67 mmol) of bromobenzene iodide was added to a 100 ml two-necked flask,Cuprous iodide (CuI) 336 mg (0.1 equ),1,8-diazabicycloundec-7-ene (DBU) 15.8 Ml (6 equ),Trimethyl ethynylsilane 1.25 Ml (0.5 equ),Phenanthroline Palladium dichloride 0.75 g (6%),Deionized water 0.125Ml (0.4equ), toluene 65mL;in room temperature,Stirring for 18 hours;After the reaction,Excessive DBU in hydrochloric acid neutralization system;Dry the toluene,Extracted twice with dichloromethane and water,Take the organic phase;The dichloromethane was removed by distillation under reduced pressure,Silica gel column purification,2 g of intermediate 1 was obtained in a yield of 34%
34% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 18h; Inert atmosphere; Schlenk technique; Darkness; Synthesis of 1,2-bis(4-bromophenyl)ethyne is representative PdCl2(PPh3)2 (168mg, 0.24 mmol, 6.0 mol%), CuI (76 mg, 0.40 mmol, 10 mol%) and 1-bromo-4-iodobenzene (1.1 g, 4.0 mmol) were added into a 50-mL 2-neck round-bottom flaskwith a magnetic stirring bar. The flask was evacuated and refilled with N2 gasfollowing the usual Schlenk technique. Dry toluene (20 mL) was added while stirring.N2-sparged DBU (3.6 mL, 24 mmol, 6.0 equiv), trimethylsilylacetylene (0.28 mL, 2.0mmol, 1.0 equiv) and distilled water (29 μL, 1.6 mmol, 40 mol%) were addedconsecutively. The reaction flask was wrapped with aluminum foil and stirred at roomtemperature for 18 h. The reaction was quenched with water (20 mL) and extractedwith diethyl ether (20 mL). The organic layer was washed with 10% aqueous HCl (3 15 mL), brine (20 mL), dried over Na2SO4, gravity-filtered and the solvent removedin vacuo. The crude product was purified by silica gel column chromatography inhexane and concentrated in vacuo to obtain 1b in 34% (229 mg, 0.68 mmol) yield aswhite crystals.1
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Inert atmosphere;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 70℃; for 20h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60℃; for 18h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60 - 80℃; for 24h; Sealed tube; Inert atmosphere;

Reference: [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]
[2]Walia, Preet Kamal; Pramanik, Subhamay; Bhalla, Vandana; Kumar, Manoj [Chemical Communications, 2015, vol. 51, # 97, p. 17253 - 17256]
[3]Mio, Matthew J; Kopel, Lucas C; Braun, Julia B; Gadzikwa, Tendai L; Hull, Kami L; Brisbois, Ronald G; Markworth, Christopher J; Grieco, Paul A [Organic letters, 2002, vol. 4, # 19, p. 3199 - 3202]
[4]Cheng, Shengli; Zong, Lishuai; Yuan, Kuanyu; Han, Jianhua; Jian, Xigao; Wang, Jinyan [RSC Advances, 2016, vol. 6, # 91, p. 88403 - 88410]
[5]Mandali, Pavan Kumar; Chand, Dillip Kumar [Catalysis Communications, 2014, vol. 47, p. 40 - 44]
[6]Guo, Wusheng; Pleixats, Roser; Shafir, Alexandr; Parella, Teodor [Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 89 - 99]
[7]Rakshit, Souvik; Patureau, Frederic W.; Glorius, Frank [Journal of the American Chemical Society, 2010, vol. 132, # 28, p. 9585 - 9587]
[8]He, Zuozheng; Cai, Xinyi; Wang, Zhiheng; Li, Yunchuan; Xu, Zhida; Liu, Kunkun; Chen, Dongcheng; Su, Shi-Jian [Journal of Materials Chemistry C, 2017, vol. 6, # 1, p. 36 - 42]
[9]Hou, Duen-Ren; Kuan, Ting-Chun; Li, Yu-Kai; Lee, Richmond; Huang, Kuo-Wei [Tetrahedron, 2010, vol. 66, # 48, p. 9415 - 9420]
[10]Chen, Hua; Haiyan, Fu; Jiang, Weidong; Li, Ruixiang; Li, Shun; Li, Wenjing; Tang, Juan; Xu, Bin; Yuan, Maolin; Zheng, Xueli [Organic Letters, 2020, vol. 22, # 20, p. 7814 - 7819]
[11]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN106242976, 2016, A Location in patent: Paragraph 0048; 0049; 0050; 0051
[12]Yip, Shu Jan; Yoshidomi, Tetsushi; Murakami, Kei; Itami, Kenichiro [Chemistry Letters, 2018, vol. 47, # 3, p. 329 - 331]
[13]Location in patent: scheme or table Weber, Lothar; Eickhoff, Daniel; Werner, Vanessa; Boehling, Lena; Schwedler, Stefanie; Chrostowska, Anna; Dargelos, Alain; MacIejczyk, Malgorzata; Stammler, Hans-Georg; Neumann, Beate [Dalton Transactions, 2011, vol. 40, # 17, p. 4434 - 4446]
[14]Chen, Hua; Zhu, Haoyun; Huang, Yuli; Yang, Junwei; Wang, Weizhi [Chemistry - An Asian Journal, 2017, vol. 12, # 23, p. 3016 - 3026]
[15]Xu, Hua-Jin; Kang, Yan-Shang; Shi, Hang; Zhang, Ping; Chen, You-Ke; Zhang, Bing; Liu, Zhi-Qiang; Zhao, Jing; Sun, Wei-Yin; Yu, Jin-Quan; Lu, Yi [Journal of the American Chemical Society, 2019, vol. 141, # 1, p. 76 - 79]
[16]Raju, Selvam; Hsiao, Huan-Chang; Thirupathi, Selvakumar; Chen, Pei-Ling; Chuang, Shih-Ching [Advanced Synthesis and Catalysis, 2019, vol. 361, # 4, p. 683 - 689]
  • 11
  • [ 2789-89-1 ]
  • [ 17865-11-1 ]
  • [ 647851-32-9 ]
  • 13
  • [ 52997-43-0 ]
  • [ 2789-89-1 ]
  • 4,4'-bis(2-hexyldecyl)diphenylacetylene [ No CAS ]
  • 14
  • [ 2789-89-1 ]
  • 2,3,4,5-tetrakis(4-bromophenyl)furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With oxygen; copper diacetate; palladium diacetate; acetic acid at 100℃; for 12h; Green chemistry;
86% With octadecafluorodecahydronaphthalene (cis+trans); oxygen; palladium diacetate; zinc(II) chloride In N,N-dimethyl acetamide at 60℃; for 24h; sealed tube;
41% With water; oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide at 80℃; for 6h; Autoclave;
Multi-step reaction with 2 steps 1: 25 percent / CF3COOH, PbO2 / CH2Cl2 / 3 h / 20 °C 2: 40 percent / conc. HI / 0.5 h / Heating

  • 15
  • [ 766-96-1 ]
  • [ 589-87-7 ]
  • [ 2789-89-1 ]
YieldReaction ConditionsOperation in experiment
100% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere;
97% With C18H18N2O8PdS2(2-)*2Na(1+)*3H2O; triethylamine In lithium hydroxide monohydrate at 80℃; for 8h;
91% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide
81% With [2,2]bipyridinyl; Cs2CO3; iron(III) acetylacetonate In toluene at 135℃; for 42h; Inert atmosphere;
77% With pyridine; n-propylamine at 20℃; for 24h;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine for 120h; Inert atmosphere;
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In tetrahydrofuran at 50℃; for 24h; Sealed tube; Inert atmosphere; To a 50 mL test tube was added the crude product from above (0.306 g, 1.69 mmol), 1-bromo-4-iodobenzene(0.478 g, 1.69 mmol), Pd(PPh3)4 (0.057 g, 0.05 mmol), and CuI (0.019 g, 0.10 mmol). To a separate test tubewas added tetrahydrofuran (20 mL), and triethylamine (5 mL). Each tube was sealed with a rubber septumand purged with a continuous stream of argon (5 min). The contents of the liquids tube were transferred tothe solids tube via cannula under argon. The resulting mixture was stirred at 50C under argon for 24 h. Theresulting suspension was extracted between dichloromethane and 5% NH4OH (aq). The organic layer wasseparated and dried over MgSO4. After filtration to remove the drying agent, the solvent was removed viarotary evaporation to give a brown-orange powder. 1H NMR spectrum matched that previously described.8This crude 4,4’-dibromotolane product was used directly in the next step without further purification.
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 6h; Inert atmosphere;
5.48 g With copper (I) iodide; trans-bis(triphenylphosphine)palladium(II) dichloride; N,N-diisopropylamine In tetrahydrofuran at 20℃; for 15h; Inert atmosphere;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine; triphenylphosphine at 25 - 40℃; for 24h; Inert atmosphere; Sealed tube;
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; N,N-diisopropylamine In tetrahydrofuran at 40℃; Inert atmosphere;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In lithium hydroxide monohydrate; benzene at 80℃;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triphenylphosphine In tetrahydrofuran; triethylamine at 20℃; Inert atmosphere; Schlenk technique;
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;
Stage #1: 1,4-bromoiodobenzene With tetrahydropyrrole; palladium (II) chloride In lithium hydroxide monohydrate at 50℃; for 0.0833333h; Stage #2: 4-bromo-1-ethynylbenzene In lithium hydroxide monohydrate at 50℃; for 12h;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In lithium hydroxide monohydrate; benzene at 80℃;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In lithium hydroxide monohydrate; toluene at 80℃; for 18h;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide at 20℃; for 12h; Inert atmosphere;

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[2]Voronova, Krisztina; Homolya, Levente; Udvardy, Antal; Benyei, Attila C.; Joo, Ferenc [ChemSusChem, 2014, vol. 7, # 8, p. 2230 - 2239]
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[6]Location in patent: experimental part Weisheit, Thomas; Escudero, Danie; Petzold, Holm; Goerls, Helmar; Gonzalez, Leticia; Weigand, Wolfgang [Dalton Transactions, 2010, vol. 39, # 40, p. 9493 - 9504]
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[8]Chen, Xuebing; Wu, Youzhi; Xu, Jinyi; Yao, Hequan; Lin, Aijun; Huang, Yue [Organic and Biomolecular Chemistry, 2015, vol. 13, # 35, p. 9186 - 9189]
[9]Marinelli, Davide; Fasano, Francesco; Najjari, Btissam; Demitri, Nicola; Bonifazi, Davide [Journal of the American Chemical Society, 2017, vol. 139, # 15, p. 5503 - 5519]
[10]Raju, Selvam; Hsiao, Huan-Chang; Thirupathi, Selvakumar; Chen, Pei-Ling; Chuang, Shih-Ching [Advanced Synthesis and Catalysis, 2019, vol. 361, # 4, p. 683 - 689]
[11]Guo, Songjin; Li, Panpan; Guan, Zhe; Cai, Libo; Chen, Siwei; Lin, Aijun; Yao, Hequan [Organic Letters, 2019, vol. 21, # 4, p. 921 - 925]
[12]Yuan, Hairui; Wang, Min; Xu, Zhenghu; Gao, Hongyin [Advanced Synthesis and Catalysis, 2019, vol. 361, # 18, p. 4386 - 4392]
[13]Li, Tongyu; Liu, Chang; Wu, Shaonan; Chen, Chen C.; Zhu, Bolin [Organic and Biomolecular Chemistry, 2019, vol. 17, # 33, p. 7679 - 7683]
[14]Yang, Qi-Liang; Xing, Yi-Kang; Wang, Xiang-Yang; Ma, Hong-Xing; Weng, Xin-Jun; Yang, Xiang; Guo, Hai-Ming; Mei, Tian-Sheng [Journal of the American Chemical Society, 2019, vol. 141, # 48, p. 18970 - 18976]
[15]Qian, Lei-Lei; Min, Xiang-Ting; Hu, Yan-Cheng; Shen, Bing-Xue; Yang, Sa-Na; Wan, Boshun; Chen, Qing-An [Chemical Communications, 2020, vol. 56, # 17, p. 2614 - 2617]
[16]Li, Ming; Yao, Tian-Yu; Sun, Sheng-Zheng; Yan, Ting-Xun; Wen, Li-Rong; Zhang, Lin-Bao [Organic and Biomolecular Chemistry, 2020, vol. 18, # 16, p. 3158 - 3163]
[17]Wu, Shaonan; Wang, Zhuo; Bao, Yinwei; Chen, Chen; Liu, Kun; Zhu, Bolin [Chemical Communications, 2020, vol. 56, # 32, p. 4408 - 4411]
[18]He, Yuan; Liao, Xian-Zhang; Dong, Lin; Chen, Fen-Er [Organic and Biomolecular Chemistry, 2021, vol. 19, # 3, p. 561 - 567]
[19]Rakshit, Amitava; Dhara, Hirendra Nath; Sahoo, Ashish Kumar; Alam, Tipu; Patel, Bhisma K. [Organic Letters, 2022, vol. 24, # 20, p. 3741 - 3746]
  • 16
  • [ 2789-89-1 ]
  • [ 620624-92-2 ]
  • [ 1119260-67-1 ]
YieldReaction ConditionsOperation in experiment
76% With tetraethylammonium hydroxide In water; toluene at 90℃; for 14h; 4.a; 12 2-Pinacolborolane-7-trimethylsilyl-9,9-dioctylfluorene (3.5 g, 6 mmol), 4,4'- dibromophenylacetylene (1 g, 3 mmol) and Pd(PPh3)4 (50 mg) were dissolved in degassed toluene (30 ml_). Tetraethylammonium hydroxide solution (20% wt. in water, 10 ml_) was thoroughly degassed and added to the reaction mixture. The resulting solution was heated at 90 5C for 14 h and the product was extracted into toluene. The toluene solution was dried over MgSO4 and filtered through a plug of silica. A pale yellow solid (2.5 g, 76% yield) was obtained after column chromatography (SiO2, Pet. Spirits/CH2CI2 3:1 , Rf 0.6) and precipitation from methanol. White crystals were obtained from recrystallisation with isopropanol for analysis, m.p. 171 0C.1H NMR (500 MHz, CDCI3, δ): 0.36 (s, 18H, TMS), 0.75 (br, 8H, -CH2-), 0.83 (t, J l, 12H, -CH3), 1.10 (br m, 4OH, -CH2-), 2.04 (m, 8H, -CH2-), 7.52-7.80 (m, 2OH, ArH). 13C NMR (125 MHz, CDCI3, δ): -0.9, 14.1 , 22.6, 23.8, 29.1 , 29.2, 29.9, 31.8, 40.2, 55.1 , 90.2, 1 19.1 , 120.1 , 121 .3, 122.0, 125.9, 127.0, 127.6, 131.9, 132.0, 139.2, 140.8, 141.2, 141.5, 150.2, 151 .7. MS-EI (m/z): M+ 1099.3. Elemental analysis: cal. C 85.18, H 9.71 ; found C 85.31 , H 9.74.
With tetrakis(triphenylphosphine) palladium(0); tetraethylammonium hydroxide In water; toluene at 100℃; for 14h; Inert atmosphere;
  • 17
  • [ 2789-89-1 ]
  • [ 762-04-9 ]
  • [ 1208127-35-8 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In toluene at 75℃; Inert atmosphere; III.D.1 III.D.1 Synthesis of bis(4-diethylphosphoϖatophenyl)acetylene (a)Bis(4-bromophenylacetylene) (1.384 g, 4 mmol) was dissolved in anhydrous toluene (85 ml) and stirred under argon until it was dissolved. Diethyl phosphite(6.31 ml, 48 mmol) and triethylamine (4.92 ml, 48 mmol) were added with a syringe, and the mixture was stirred for an additional 10 min; finally tetrakis(triphenylphosphine)palladium (0) (1.16 g, 1 mmol) was added with a high argon purge and the mixture heated at 75 0C overnight. After cooling to room temperature, diethyl ether was added to the reaction mixture to precipitate the triethylamine hydroiodide, which was removed by filtration. The filtrate was evaporated to give a yellowish oil. The crude product was purified by column chromatography on silica gel (ethyl acetate/methanol = 10/1). 1.47 g (82 %) of a white solid was obtained.MS (70 eV): m/z = 450.5, calcd.: 450.4 (M+).1H NMR (250 MHz, CD2CI2): δ ppm 7.85 - 7.71 (m, 4H), 7.69 - 7.54 (m, 4H), 4.21 -3.91 (m, 8H), 1.36 - 1.20 (m, 12H).13C NMR (75 MHz, CD2CI2): δ ppm 132.26, 132.15, 132.13, 131.95, 130.98,128.48, 127.19, 127.14, 91.17, 62.77, 62.70, 16.70, 16.62.31P NMR (200 MHz, CD2CI2): δ ppm 15.20.
  • 18
  • [ 589-87-7 ]
  • [ 994-71-8 ]
  • [ 2789-89-1 ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; Bis(4-bromophenyl)acetylene (7).5 Tetrakis(triphenylphosphino) palladium(0) (0.348 g, 1.5 mol%), triphenylphosphine (30 mg, 0.52 mol%), 1-bromo-4-iodobenzene (12.45 g, 44.00 mmol, 2.0 eq.), 1 (12.1 g, 21.9 mmol) and p-dioxane (50 mL) were combined in a Schlenk flask and heated to 100 °C for 2 h. Upon cooling, yellow crystals formed and were filtered and washed with cold hexanes. The resulting crystals were combined with hexanes (50 mL), heated to reflux for 5 minutes, left to cool to room temperature overnight and filtered, resulting in pale yellow crystals of 7 (6.01 g, 82%). m. p.: 177-180 °C (dec.). 1H NMR (CDCl3; 300.17 MHz): d 7.43 (dd, J = 37.3 Hz, J = 9.7 Hz) 13C NMR (CDCl3; 75.485 MHz): d 133.0 (C-H), 131.7 (C-H), 122.8, 121.9, 89.4 (acetylene). UV/Vis (toluene): lmax 313 nm (e = 42,300).
  • 19
  • [ 589-87-7 ]
  • [ 75-20-7 ]
  • [ 2789-89-1 ]
YieldReaction ConditionsOperation in experiment
97% With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine In acetonitrile at 20℃; Inert atmosphere; 4.2. General procedure for Pd-catalyzed coupling reaction of calcium carbide with aryl iodides General procedure: A 100 mL round bottom flask with a magnetic stir bar was charged with copper iodide (0.1 equiv), palladium acetate (0.05 equiv), and triphenylphosphine (0.1 equiv) in acetonitrile. The solution was degassed with nitrogen for 20 min. Then, triethylamine (3 equiv), aryl iodides (1 equiv), and calcium carbide (3 equiv) were added. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The reaction mixture was then filtrated through a short plug of silica gel and washed with hexane. The filtrate was evaporated under vacuum to give the desired compound.
With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine In acetonitrile at 20℃; Inert atmosphere;
  • 20
  • [ 2789-89-1 ]
  • [ 1352050-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate 2: formic acid; methanesulfonic acid; hydrogen bromide; dimethyl sulfoxide / acetic acid / 24 h / 110 °C
  • 21
  • [ 2789-89-1 ]
  • [ 62-53-3 ]
  • [ 1403495-29-3 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 1,2-bis(4-bromophenyl)acetylene; aniline With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride In tert-Amyl alcohol at 40℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With sodium hydroxide In methanol; tert-Amyl alcohol at 20℃; for 1h;
75% With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride In pentan-1-ol at 100℃; for 24h; 31 Example 31, 2,3-di(4-bromophenyl)-indole 3ae The aniline to 1a (55. 0μL, 0 . 6mmol), 1,2-bis(4-bromophenyl) acetylene 2e (134.4 mg, 0 . 4mmol), Cp*Rh (H2O)3(OTf)2(11.8 mg, 5mol %), acetic anhydride (59. 0μL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100 degrees reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography get the pure product 2,3-di(4-bromophenyl)-indole 3ae. The product is white solid, yield 75%.
69% With copper diacetate; palladium dichloride In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere;
  • 22
  • [ 201230-82-2 ]
  • [ 2789-89-1 ]
  • (E)-2,3-bis(4-bromophenyl)acrylaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With C34H51NP2; hydrogen; palladium(II) acetylacetonate; toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 20h; Schlenk technique; Autoclave; Inert atmosphere; stereoselective reaction;
72% With bis(acetylacetonato)palladium(II); 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); hydrogen; toluene-4-sulfonic acid In tetrahydrofuran at 100℃; for 20h; stereoselective reaction;
  • 23
  • [ 23115-42-6 ]
  • [ 2789-89-1 ]
  • ethyl 1-acetyl-4,5-bis(4-bromophenyl)-1H-pyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With potassium hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In water at 110℃; for 4h; Inert atmosphere; General procedure for the ruthenium(II) catalyzed oxidative annulation of N-acetyl enamides with alkynes to substituted pyrroles General procedure: A reaction tube was charged with N-acetylenamide 1a (100 mg, 0.636 mmol), alkyne 2a (124 mg, 0.699 mmol), Cu(OAc)2.H2O (126 mg, 0.636 mmol), KPF6 (23.4 mg, 0.127 mmol) and [RuCl2(p-cymene)]2 (7.8 mg, 0.0127 mmol). To that, DME or water (3 mL) was added by syringe. The reaction mixture was stirred at 110 °C under N2 as indicated time in the table 1.The reaction mixture was cooled down to rt, diluted with 10 mL of DCM. The mixture was then filtered through Celite. The combined organic portion was washed with water, then dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel with hexane/ethyl acetate as eluent to yielded the desired pyrrole 3a (202 mg, 0.605 mmol) in 95% yield. Products obtained in this work were characterized by spectral methods particularly with 1H, 13C NMR, and ESI-Mass analyses, further, the data were compared with those reported.
  • 24
  • [ 2789-89-1 ]
  • [ 6190-28-9 ]
  • [ 1454909-04-6 ]
YieldReaction ConditionsOperation in experiment
87% With potassium dihydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In <i>tert</i>-butyl alcohol for 30h; 125 Example 125 Preparation of N-phenyl-3,4-di(p-bromophenyl)-1-phenyl-1,2-dihydrobenz[c-1,2]azaphosphinine 1-oxide Example 125 Preparation of N-phenyl-3,4-di(p-bromophenyl)-1-phenyl-1,2-dihydrobenz[c-1,2]azaphosphinine 1-oxide N-phenyl-3,4-di(p-bromophenyl)-1-phenyl-1,2-dihydrobenz[c-1,2]azaphosphinine 1-oxide (81.9 mg, 87%) as a target compound was obtained under the condition of 110 for 30 hours, by the same reaction as the Example 118 above, except for using 1,2-bis(4-bromophenyl)ethyne (100.8 mg, 0.3 mmol) instead of using 3-hexyne of the Example 118 above. 1H NMR (400 MHz, CDCl3) δ 7.68 (dd, J=7.1 Hz, 12.9 Hz, 2H), 7.51 (dd, J=7.4 Hz, 14.2 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.38-7.35 (m, 3H), 7.31-7.25 (m, 3H), 7.11-7.06 (m, 3H), 7.01-7.00 (m, 4H), 6.88 (t, J=7.8 Hz, 4H), 6.81 (t, J=7.2 Hz, 1H)
With potassium dihydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; silver carbonate In <i>tert</i>-butyl alcohol at 110℃; for 16h;
  • 25
  • [ 2789-89-1 ]
  • [ 1707-03-5 ]
  • 3,4-bis(4-bromophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol at 90℃; for 30h;
57% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol at 90℃; for 30h; 45 Example 45 Preparation of 3,4-Bis(4-bromophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide Example 45 Preparation of 3,4-Bis(4-bromophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide 3,4-Bis(4-bromophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide (47.2 mg, 57%) as a target product was obtained under the condition of 90° C. for 30 hours, by the same reaction as the Example 1 above, except for using diphenylphosphinic acid (32.7 mg, 0.15 mmol) instead of using phenylphosphonic monoethyl ester of the Example 1 above, and using 1,2-bis(4-bromophenyl)ethyne (75.6 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. 1H NMR (400 MHz, CDCl3) δ 7.94-7.89 (m, 2H), 7.66-7.51 (m, 6H), 7.47 (tt, J=7.7, 1.2 Hz, 1H), 7.39-7.34 (m, 1H), 7.28 (app d, J=8.7 Hz, 2H), 7.15 (d, J=8.2 Hz, 2H), 7.09 (app d, J=8.7 Hz, 2H), 7.01 (dd, J=8.0, 4.7 Hz, 1H).
56% With potassium hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol at 90℃; for 30h;
25% With chloropyridinecobaloxime(III); cesium fluoride; 9‑mesityl-10-methylacridinium perchlorate In chloroform; water at 20℃; Inert atmosphere; Irradiation; Schlenk technique;

  • 26
  • [ 3376-24-7 ]
  • [ 2789-89-1 ]
  • [ 1380243-26-4 ]
  • 27
  • [ 2789-89-1 ]
  • [ 95-55-6 ]
  • [ 3164-13-4 ]
  • 28
  • [ 2789-89-1 ]
  • [ 23958-29-4 ]
YieldReaction ConditionsOperation in experiment
95% With formic acid; gold nanoparticles on rutile titania; triethylamine In acetone at 60℃; for 2h; stereoselective reaction;
95% With hydrogen In acetonitrile at 110℃; for 15h; chemoselective reaction;
81% With C14H29BrMnNO2P2; potassium <i>tert</i>-butylate; hydrogen In n-heptane at 60℃; for 16h; stereoselective reaction;
With methanol; C22H35ClCuN5; bis(pinacol)diborane; sodium t-butanolate In N,N-dimethyl-formamide at 80℃; for 22h; stereoselective reaction;

  • 29
  • [ 17702-41-9 ]
  • [ 2789-89-1 ]
  • [ 71482-43-4 ]
YieldReaction ConditionsOperation in experiment
96% With <i>N</i>,<i>N</i>-dimethyl-aniline In toluene at 110℃; for 17h; Inert atmosphere; 1.2.1 Synthesis of CB-Br Under N2 atmosphere, a mixture of decaborane (B10H14, 0.501g, 4.46 mmol), 1-bromo-4-[2-(4-bromophenyl)ethynyl] benzene (1 g, 2.98 mmol) and N,N-dimethylaniline (1.13 mL, 11.16 mmol) in 30 mL distilled toluene was stirred at 110 for 17 h. After cooling the mixture to room temperature, the solvent was removed under reduced pressure and the residue was purified by column chromatography silica gel using n-hexane/ ethyl acetate (v/v, 100:1) as the eluent to obtained CB-Br as white solid (1.30 g, 96%). 1H NMR (600 MHz, CD2Cl2, δ): 7.32 (dd, J=24 Hz, 8H; Ar-H); 3.15-1.85 (m, 10H; BH). 13C NMR (600 MHz, CD2Cl2, δ): 132.59, 132.14, 129.93, 125.75,84.82.
76% In <i>N</i>,<i>N</i>-dimethyl-aniline; toluene at 110℃; for 49h; Inert atmosphere; 1 Under the protection of argon, the reactant decaborane (1.22g, 10mmol) was dissolved in 80mL toluene in a two-neck flask with reflux condenser device, and then the nucleophile N,N-dimethylaniline (1.75mL , 13.8mmol), after stirring at room temperature for 1h, add another reactant bis(4-bromophenyl)acetylene (3g, 9mmol), reflux for 48 hours at an oil bath temperature of 110, cool to room temperature, filter to remove insoluble The product is evaporated to remove the volatile solvent to obtain a crude product, and the crude product is purified by column chromatography (eluent is petroleum ether/dichloromethane v/v=10:1). After evaporating the eluent, recrystallize in dichloromethane/n-hexane with a volume ratio of 1:(1-1.5) to obtain a pure white solid product 2 (bis(4-bromophenyl)carborane, 3.1g) , the yield is 76%).
69% With <i>N</i>,<i>N</i>-dimethyl-aniline In toluene Inert atmosphere;
In toluene Inert atmosphere; Schlenk technique;

  • 30
  • [ 88-61-9 ]
  • [ 2789-89-1 ]
  • 3,4-bis(4-bromophenyl)-6,8-dimethylbenzo[c][1,2]oxathiine 1,1-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,4-dioxane at 100℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique;
  • 31
  • [ 5378-52-9 ]
  • [ 2789-89-1 ]
  • 3,4-bis(4-bromophenyl)-2-aminoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate; copper(II) acetate monohydrate; In N,N-dimethyl-formamide; at 120℃; for 6.0h;Sealed tube; Inert atmosphere; Green chemistry; 0.1680 g were weighed in this order1,2-bis (4-bromophenyl) acetylene (0.5 mmol),0 ? 2191 g of <strong>[5378-52-9]phenyl-1H-tetrazole</strong> (1.5 mmol),0 ? 0031 g [Cp * RhCl2] 2 (0. 005 mmol),0 ? 1997g Cu (OAc) 2 .H20 (1.0mmol) and0,0984 g of potassium acetate (1.O mmol) was addedIn a 25 mL sealed tube containing a magnetic stir bar,2. OmL N, N-diethylformamide was added.The cannula was sealed under nitrogen,The mixture was stirred in an oil bath at 120 C for 6 hours.After the end of the reaction, the column was separated with petroleum ether-ethyl acetate as the eluent,To give 0.1066 g of a white solid, The target productThe isolated yield of 3,4-bis (4-bromophenyl) -2-aminoisoquinoline was 46%.
  • 32
  • [ 2789-89-1 ]
  • C31H25ClO3S [ No CAS ]
  • C45H33Br2ClO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% In 1,3,5-trimethyl-benzene at 160℃; for 46h; Inert atmosphere; General procedure: A 7 ml screw-cap tube, containing a magnetic stirring bar, was flame-dried undervacuum and filled with nitrogen after cooling to room temperature. To this tube wereadded tetraarylthiophene S-oxide 6 (0.03 mmol, 1.0 equiv.), diarylethyne 7 (0.06 mmol,2.0 equiv.) and mesitylene (200 μl) under a stream of nitrogen. The flask was heatedat 160 °C for 48 h. After cooling the reaction mixture to room temperature, themixture was concentrated in vacuo and the residue was purified by preparativethin-layer chromatography to afford the corresponding HAB 9.
  • 33
  • [ 1144506-47-7 ]
  • [ 2789-89-1 ]
  • 2-octyl-5,6-bis(4-bromophenyl)-8-methyl-2H-[1,2,3]triazolo[5,1-a]isoquinolin-4-ium-1-olate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; di-tert-butyl peroxide; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 100℃; for 24h; Sealed tube;
39% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 100℃; for 24h; 14 Example 14 In 25mL dry pressure reaction tube, was added 58mg of 1-octyl-4- (p-chlorophenyl) -1,2,3-triazole, 134mg of 1-phenyl-1-propyne, 6mg of dichloro (pentamethylcyclopentadienyl yl) rhodium dimer, 80mg of copper acetate monohydrate, 32mg 1.5mL sodium peroxide and 1,2-dichloroethane.100 stirred for 24 hours.After the reaction was cooled to room temperature, directly on a silica gel column (ethyl acetate and petroleum ether, the volume ratio of 1: 3) to give product 48mg, 39% yield,
  • 34
  • [ 2789-89-1 ]
  • [ 201024-81-9 ]
  • 2-(phenyl)-3-(4-bromophenyl)-3-(4-bromobenzoyl)-2,3-dihydro-1H-indole [ No CAS ]
  • 2-(phenyl)-3-(4-bromophenyl)-3-(4-bromobenzoyl)-2,3-dihydro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid In ethyl acetate at 80℃; for 15h; Sealed tube; Inert atmosphere; diastereoselective reaction; General procedure for the synthesis of compounds 3 General procedure: Nitrones (0.2 mmol), diarylacetylenes (0.3 mmol), [Cp*RhCl2]2 (4 mol%), AgSbF6 (16 mol%), PivOH (2.0 equiv)and ethyl acetate (2 mL) were charged into the sealed tube. The reaction mixture was stirred at 80 °C for 15 h. After cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using triethylamine/PE or PE/EA to afford compounds 3.
72 % de With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; trimethylpyruvic acid In 1,4-dioxane at 50℃; for 12h; Molecular sieve; Inert atmosphere; Overall yield = 58 %;
  • 35
  • [ 15563-32-3 ]
  • [ 2789-89-1 ]
  • [ 1380243-26-4 ]
YieldReaction ConditionsOperation in experiment
70% With silver hexafluoroantimonate; [RhCp*(CH3CN)3] (SbF6)2; copper(II) acetate monohydrate In diethylene glycol dimethyl ether at 140℃; for 4h; Inert atmosphere; General Procedure for the Reaction of Thioamides with Alkynes General procedure: To a 20 mL two-necked flask with a reflux condenser, a balloon, and a rubber cup were added thioamide 1 (0.25 mmol), alkyne 4 (0.25 mmol), [Cp*Rh(MeCN)3][SbF6]2 (0.01 mmol, 8.3 mg), AgSbF6 (0.04 mmol, 14 mg), Cu(OAc)2•H2O (0.5 mmol, 100 mg), dibenzyl (ca. 30 mg) as internal standard, and diglyme (3 mL). Then, the resulting mixture was stirred under nitrogen at 140 °C (bath temperature) for 4 h. After cooling, to the reaction mixture were added water (30 mL) and ethylenediamine (2 mL). The mixture was extracted with ethyl acetate (3x30 mL) and dried over Na2SO4. After evaporation of the solvents under vacuum, product 5 was isolated by column chromatography using eluent shown below. Further purification by gel permeation chromatography (GPC) was performed, if needed.
  • 36
  • [ 613-91-2 ]
  • [ 2789-89-1 ]
  • [ 1314243-16-7 ]
YieldReaction ConditionsOperation in experiment
78% With carbonyl(η-5-cyclopentadienyl)diiodocobalt(III); potassium acetate In 2,2,2-trifluoroethanol at 100℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; Green chemistry;
41% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper(II) acetate monohydrate; Trimethylacetic acid In methanol at 120℃; for 24h; Sealed tube; regioselective reaction; Characterization data of 4 are represented as follows General procedure: A mixture of acetophenone oxime 1a (0.2 mmol), diphenylacetylene 2 (0.24 mmol, 1.2 equiv), [Cp*IrCl2]2 (3 mol%), PivOH (0.06 mmol, 0.3 equiv), Cu(OAc)2. H2O (0.4 mmol, 2 equiv) and MeOH (2 mL) in a 15mL glass vial [sealed with poly(tetrafluoroethylene)(PTFE) cap] was heated at 120 °C with vigorous stirring for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through Celite. The filtrate was concentrated in vacuo and purified by column chromatography on silica gel to give the corresponding product 4.
  • 37
  • [ 101-42-8 ]
  • [ 2789-89-1 ]
  • 2,3-bis(4-bromophenyl)-N,N-dimethyl-1H-indole-1-carboxamide [ No CAS ]
  • 38
  • [ 2789-89-1 ]
  • C29H22Br2O [ No CAS ]
  • [ 19057-50-2 ]
  • 39
  • bis-(1-<i>p</i>-tolyl-ethylidene)-hydrazine [ No CAS ]
  • [ 2789-89-1 ]
  • [ 1613470-80-6 ]
YieldReaction ConditionsOperation in experiment
56% With Cp*Rh(H2O)3(OTf)2; benzoic acid In methanol at 25℃; for 24h; 76 Example 76, isoquinoline 4bf The phenylhydrazone 4b (0.3mmol), 1,2-bis(4-bromophenyl) acetylene 2f(0.5mmol), Cp*Rh (H2O)3(OTf)2(0.01mmol), benzoic acid (0.125mmol), by adding 4.0 ml methanol, the air lower, 25oC reaction 24 hours after cessation of the reaction, pure product of column chromatography to obtain isoquinoline 4bf. The product is white solid, yield 56 %.
  • 40
  • [ 2789-89-1 ]
  • [ 122920-01-8 ]
  • C40H24Br2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In tetrahydrofuran at 120℃; for 12h; Schlenk technique; Inert atmosphere; Ru(II)-catalyzed C-H funciotnalization of 2-acetyltetraphenylene withalkynes General procedure: A 25 mL Schlenk-type tube (with a Teflon high pressure valve and side arm) was charged withcompound 1a (34.6 mg, 0.10 mmol), alkynes (0.20 mmol), Cu(OAc)2.H2O (5.0 mg, 0.025 mmol),[RuCl2(p-cymene)]2 (6.1 mg, 0.01 mmol), AgSbF6 (13.7 mg, 0.04 mmol) and THF (1 mL). Thereaction tube was evacuated and back-filled with N2 (3 times, ballon). After the reaction mixturewas stirred at 120 oC for 12 h, it was allowed to cool down to room temperature. The reactionmixture was diluted with ethyl acetate (20 mL), and then filtered through a pad of Celite. Thefiltrate was washed with brine (10 mL), dried over Na2SO4, and concentrated in vacuo. Theresidue was purified by silica gel preparative TLC to give the corresponding products
  • 41
  • [ 38707-70-9 ]
  • [ 2789-89-1 ]
  • C38H23Br4NO [ No CAS ]
  • 42
  • [ 38707-70-9 ]
  • [ 2789-89-1 ]
  • C38H22Br5NO [ No CAS ]
  • 43
  • [ 934-37-2 ]
  • [ 2789-89-1 ]
  • 3,4-bis(4-bromophenyl)-2-methylimidazo[5,1,2-cd]indolizine [ No CAS ]
  • 44
  • [ 2789-89-1 ]
  • [ 406207-65-6 ]
  • 3,4-bis(4-bromophenyl)-2-tert-butylimidazo[5,1,2-cd]indolizine [ No CAS ]
  • 46
  • [ 1008-89-5 ]
  • [(eta.(5)-pentamethylcyclopentadienyl)Rh(H2O)3](OTf)2 [ No CAS ]
  • [ 1493-13-6 ]
  • [ 2789-89-1 ]
  • [ 1440420-81-4 ]
YieldReaction ConditionsOperation in experiment
49% With oxygen In methanol at 120℃; for 22h; 32 Embodiment 32, trifluoromethanesulfonic acid isoquinoline salt derivative 3ae preparation The 2 - phenylpyridyl 1a (71 μL, 0 . 5mmol), 1, 2 - b (4 - bromophenylacetic) acetylene 2e (168.0 mg, 0.5 mmol), Cp * Rh (H2 O)3 (OTf)2 (3.0 mg, 1 mol %), HOTf (44 μL, 0.5 mmol), adding 2.0 ml in methanol, oxygen (1atm), 120 o C reaction 22 hours after stopping the reaction, diatomaceous earth filter, dichloromethane washing, to collect organic phase of the drying solvent, methanol/ethyl ether/petroleum ether (1:4: 100) washing, to get the pure product isoquinoline salt derivative 3ae. The product is a white solid, yield 49%.
  • 47
  • [ 2789-89-1 ]
  • [ 122-39-4 ]
  • [ 607716-27-8 ]
YieldReaction ConditionsOperation in experiment
85% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 90℃; for 12h; Inert atmosphere; 5 Example 5 Under nitrogen protection,To a three-necked flask was added 100 ml of toluene,1 g of Intermediate 1 (2.99 mmol) prepared in Example 1,1.26 g of diphenylamine (7.45 mmol, 2.5 equ),0.90 g of sodium tert-butyl alcohol was added with stirring,59.8 mg of palladium acetate was added,0.5 mL of tri-tert-butylphosphine,90 ° C for 12 hours;The organic phase was extracted with dichloromethane,Spin dryTo give 1.30 g of product (P1) in 85% yield.
  • 48
  • [ 854952-58-2 ]
  • [ 2789-89-1 ]
  • C50H32N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 90℃; Inert atmosphere; 41 Example 41 A small molecule luminescent material (P37) based on 1,2-diphenylacetylene as the acceptor unit,The specific steps are:Under nitrogen protection,To a three-necked flask was added 100 ml of toluene,1 g of intermediate 1 (2.99 mmol),2.14 g of 9-phenyl-3-carbazole boronic acid (7.45 mmol, 2.5 equ)Under stirring, 3.47 g of sodium tert-butyl alcohol was added,Then add 230 mg of palladium acetate,0.5 mL of tri-tert-butylphosphine,90 & lt; 0 & gt; C overnight.Cooling, extraction of organic phase with methylene chloride, spin dry,Column. To give 1.48 g of product as a yellow solid in 75% yield.
  • 49
  • [ 1452-77-3 ]
  • [ 2789-89-1 ]
  • (Z)-N-(1,2-bis(4-bromophenyl)vinyl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With cesiumhydroxide monohydrate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; stereoselective reaction; Cesium Hydroxide-Mediated Hydroamidation of Internal Aryl Alkynes with Amides General procedure: The reaction of diphenylacetylene (1a) with picolinamide (2a) is representative (Table 2, entry1): In a glovebox filled with nitrogen, diphenylacetylene (1a; 45 mg, 0.25 mmol), 2-picolinamide (2a;31 mg, 0.25 mmol), and CsOH•OH2 (42 mg, 0.25 mmol) were placed in a 2-mL microwave vessel(Biotage). The vessel was sealed with a cap and then taken out of the glovebox. Dimethyl sulfoxide(DMSO, 1.0 mL) was sequentially injected via a syringe. The mixture was stirred for 24 h at 120 °C.The resulting mixture was then quenched with water. The mixture was extracted with ethyl acetatethree times, and the combined organic layer was dried over anhydrous Na2SO4. After concentrationunder reduced pressure, silica gel column purification with hexane/ethyl acetate (3/1, v/v) afforded (Z)-N-(1,2-diphenylvinyl)picolinamide (3aa; 50 mg, 0.17 mmol) in 66% yield.
  • 50
  • [ 2789-89-1 ]
  • N,2-bis(4-bromophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With trimethylsilylazide; silver carbonate; trifluoroacetic acid In water; 1,2-dichloro-ethane at 60℃; for 12h; Schlenk technique; Inert atmosphere;
50% With nitromethane; trifluoromethylsulfonic anhydride; acetic acid In formic acid at 80 - 120℃; 102 Example 102 N,2-bis(4-bromophenyl)acetamide Take a reaction tube and add 60-100mg (1.2mmol) of nitromethane, 95-105mg (0.3mmol) of 1,2-bis(4-bromophenyl)acetylene, 0.5mL of acetic acid, and 150-200mg of trifluoromethanesulfonic anhydride (0.6mmol), 30-60mg (0.75mmol) of formic acid, stirring at 80-120°C for 1-72 hours. After the reaction was completed, 10 mL of sodium hydroxide solution was added to quench the reaction, extracted with ethyl acetate 3 times, the organic phase was washed with 5 mL of brine, and the organic phases were combined and separated by column chromatography to obtain N,2-bis(4-bromophenyl)ethyl Amide 55mg, yield 50%.
50% With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;
  • 51
  • [ 318-54-7 ]
  • [ 2789-89-1 ]
  • C39H22Br4F3NO [ No CAS ]
  • C25H16Br2F3NO [ No CAS ]
  • 52
  • [ 2789-89-1 ]
  • [ 133745-75-2 ]
  • N-(2-fluoro-1,2-bis(4-bromophenyl)-2-phenylethylidene)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With Bathocuproine; cesium fluoride; copper(I) bromide In 1,2-dichloro-ethane at 70℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; Synthesis of N-(2-fluoro-1,2,2-triphenylethynlidene)benzenesulfonamide (2a) is representative General procedure: Diphenylacetylene (36 mg, 0.20 mmol), NFSI (95 mg, 0.30 mmol,1.5 equiv), bathocuproine (8.7 mg, 24 μmol, 12 mol%), CuBr (2.9 mg, 20 μmol, 10mol%) and CsF (30 mg, 0.20 mmol, 1.0 equiv) were added to a Schlenk tubecontaining a magnetic stirring bar in open air. The tube was evacuated and refilledwith N2 gas following the usual Schlenk technique. Anhydrous 1,2-dichloroethane(2.0 mL, 0.10 M) was added into the tube and the reaction tube was capped with a J.Young O-ring tap. The reaction mixture was stirred and heated at 70 °C for 12 h.The mixture was then cooled to room temperature. The crude mixture was filteredthrough a pad of silica gel topped with Na2SO4 in a short column and concentrated invacuo. 2-Fluorobiphenyl (17.2 mg, 0.10 mmol) was added into the crude as aninternal standard and the 19F NMR yield was determined. Purification by flashchromatography on silica gel (hexane/EtOAc = 7:1) followed by concentration invacuo provided 2a in 62% (53.3 mg, 0.124 mmol) yield as white crystals.
  • 53
  • [ 2789-89-1 ]
  • [ 244090-34-4 ]
  • 5,6-bis(4-bromophenyl)indolo[1,2-a]quinoline [ No CAS ]
  • 54
  • [ 2789-89-1 ]
  • [ 28144-70-9 ]
  • [ 83800-88-8 ]
YieldReaction ConditionsOperation in experiment
79% With [2,2]bipyridinyl; palladium(II) trifluoroacetate In 1,4-dioxane at 100℃; for 0.12h; 5 Example 5: Synthesis of 2-(4-bromophenyl)quinazolinone The starting material 2-aminobenzamide (0.3 mmol, 1 equiv),4,4'-dibromodiphenylacetylene (0.9 mmol,3equiv), catalyst palladium trifluoroacetate (Pd(TFA) 2, 0.03 mmol, 10%) and ligand 2,2'-bipyridine (bpy,0.06mmol, 20%) was added to the reaction vessel, and the reaction vessel was continuously subjected to three pumping-oxygenation operations, and then continued.The reaction solvent 1,4-dioxane (1,4-dioxane, 0.4 mL) was added to the reaction vessel, followed by reaction at 100 ° C in an oil bath.Stir at temperature until the end of the reaction (about 12h), then spin off the reaction solvent and pass column chromatography (filled with 300 mesh in column)400 mesh silica gel, separated by dichloromethane and ethyl acetate in a volume ratio of 10:1 as an eluent), after separation and purification, whiteSolid, yield 79%.
  • 55
  • [ 2789-89-1 ]
  • [ 611-73-4 ]
  • [ 1380243-26-4 ]
YieldReaction ConditionsOperation in experiment
73% With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate In toluene at 120℃; 4.1 General experimental procedure for the preparation of indenones General procedure: To an oven-dried screwed vial were added substituted 2-oxo-2-phenylacetic acid (0.1mmol), substituted alkyne (0.11mmol), [IrCp*Cl2]2 (0.01mmol, 7.97mg), (CH3OC6H4)3P (0.01mmol, 3.52mg), AgSbF6 (0.01mmol, 3.44mg), Cu(OAc)2 (0.02mmol, 3.99mg), and toluene (1mL). The mixture was vigorously stirred at 120°C under air to the end of the reaction. Organic solvents were removed in vacuo, and then the residue was purified by a silica gel column chromatography to give the desired product.
  • 56
  • [ 2039-49-8 ]
  • [ 2789-89-1 ]
  • 3,4-bis(4-bromophenyl)-1-[2,3,7,8-tetrakis(4-bromophenyl)benzo[de]chromen-9-yl]isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; copper diacetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; Schlenk technique; Rh-Catalyzed Annulative Coupling (Scheme 2 and Scheme 3); GeneralProcedure General procedure: A glass tube equipped with a magnetic stir bar was charged with isoxazole 1 (0.2 mmol), alkyne 2 (0.62 mmol, 3.1 equiv),[Cp*Rh(MeCN)3](SbF6)2 (0.008 mmol, 4.0 mol%), and Cu(OAc)2 (0.8mmol, 4.0 equiv). The tube was evacuated and backfilled with N2 (3 ×)followed by addition of 1,4-dioxane (4.0 mL) via syringe. The resulting mixture was heated at 100 °C for 12 h. After cooling to r.t., the mixture was poured into water and extracted with EtOAc (3 ×). The combined organic extracts were washed with brine, dried (Na2SO4), andc oncentrated under reduced pressure. The residue was subjected to column chromatography (silica gel) to afford the corresponding product .Further purification was performed by GPC if required. Note: the coupling products 3 exhibit broadened and split peaks inNMR spectra owing to the presence of rotamers, and the following data are reported as appeared in the spectra.
  • 57
  • [ 2789-89-1 ]
  • [ 19057-50-2 ]
YieldReaction ConditionsOperation in experiment
92% With dicobalt octacarbonyl; In 1,4-dioxane; at 125℃; for 7h;Schlenk technique; Inert atmosphere; In a dry Schlenk reaction bottle,Add 1.0 g of bis(4-bromophenyl)acetylene (BBPA) (2.98 mmol) dissolved in 12 mL of dry 1,4-dioxane.Then add 92.36 mg Co2(CO) 8 (0.27 mmol),O2 was removed by bubbling with nitrogen for 15 min.It was heated to 125 C under reflux for 7 hours under a nitrogen atmosphere.Cool to room temperature and spin dry the solvent.Recrystallization from dichloromethane and methanol gave a white powder product (yield: 92%).
  • 58
  • [ 2789-89-1 ]
  • [ 102-04-5 ]
  • 3-benzyl-1,2-bis(4-bromophenyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With [RhCl2(p-cymene)]2; potassium acetate; sodium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube; 4.2. General procedure for ruthenium-catalyzed annulation of 1,3-diphenylacetone with internal alkynes General procedure: A 25mL sealed tube was charged with 1,3-diphenylacetone 1a(0.2 mmol, 2.0 equiv), internal alkynes 2 (0.1 mmol, 1.0 equiv),[RuCl2(p-cymene)]2 (0.015 mmol, 15 mol%), KOAc (0.2 mmol, 2.0equiv), Na2CO3 (0.2 mmol, 2.0 equiv) and PhMe (0.5 mL). The vialwas evacuated and filled with N2 atmosphere, and stirred at 100 Cfor 24 h. After being cooled to room temperature, the mixture wasevaporated under reduced pressure. The residue was purified byflash column chromatography on silica gel, eluting with petroleumether to afford the desired products 3.
57% With [RhCl2(p-cymene)]2; potassium acetate; sodium carbonate In toluene at 100℃; for 24h; Sealed tube; Inert atmosphere; 8 Example 8 Add dibenzyl ketone (42mg, 0.2mmol) to a 25mL sealed tube with magnets,The corresponding internal alkynes (0.1 mmol),Catalyst [RuCl2(p-cymene)]2 (9mg, 15%mol),0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol),Potassium acetate (19mg, 0.2mmol), pump nitrogen three times,React at 100°C for 24 hours,Then it is separated by column chromatography (eluent: petroleum ether) to obtain the target compound. The characterization is as follows.
  • 59
  • [ 2789-89-1 ]
  • [ 23958-29-4 ]
  • [ 18869-30-2 ]
  • 60
  • [ 2789-89-1 ]
  • [ 19226-36-9 ]
  • 3,4-bis(4-bromophenyl)isoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate In methanol at 20℃; for 0.0833333h; 19 4.2. General procedure for the synthesis of isoquinolones (3) General procedure: A mixture of 3-substituted 1,4,2-dioxazol-5-ones (0.36 mmol, 1.2 equiv), alkynes (0.3 mmol), [Cp*RhCl2]2 (5.4 mg, 3.0 mmol%), KOAc (5.9 mg, 20 mmol%) was stirred in MeOH (1.5 mL) at room temperature for 5 min. The reaction was quenched with water (10 mL), then extracted with dichloromethane (15 mL x 3). The combined organic layers were washed with water (10 mL x 3) and brine (10 mL), dried over anhydrous Na2SO4 and concentrated in vacuum. Purification of the crude product by chromatography (silica gel) afforded 3a-3w. For product 3p and 3t, the reactions took place at 30 °C for 20 h.
  • 61
  • [ 1885-13-8 ]
  • [ 2789-89-1 ]
  • 5,6,7,8-tetrakis(4-bromophenyl)-3-methoxy-1-naphthoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; tetrabutylammomium bromide; 5-methyl-dihydro-furan-2-one; In N,N-dimethyl-formamide; at 100℃; for 12h; Were added p-cymene ruthenium dichloride dimer (0.01mmol, 6.1mg) in a reaction tube of 10mL branched port, bis(4-bromophenyl)acetylene (0.4 mmol, 134.4 mg), <strong>[1885-13-8]4-methoxyphthalic acid</strong> (0.3 mmol, 58.8 mg), tetrabutylammonium bromide (0.04 mmol, 12.9 mg) and a magnetic stir bar were added with a pipette to add 900 muL of GVL and 100 muL of DMF. The upper opening of the reaction tube was capped and the branch was allowed to communicate with the air, and then placed in a metal heating module at 100 C for 12 hours. After the reaction is completed, ethyl acetate is added, washed with water, and separated, and the organic phase is concentrated, and then subjected to silica gel column chromatography.The pale yellow solid was obtained as the product 5,6,7,8-tetrakis(4-bromophenyl)-3-methoxy-1-naphthoic acid, yield 81%
  • 62
  • [ 2565-18-6 ]
  • [ 2789-89-1 ]
  • 3,4,7,8-tetrakis(4-bromophenyl)-2,6-dibutyl-2,6-dihydro-2,6-naphthyridin-1,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With dirhodium tetraacetate; silver hexafluoroantimonate; silver carbonate; In toluene; at 20℃;Reflux; The preparation method is as follows: A toluene solution of <strong>[2565-18-6]N-butylacrylamide</strong> is added to a clean 30 mL round bottom flask placed with stirring magnets. At a concentration of 1 M, then the catalyst cerium acetate (10 mol%) was added. Oxidant silver carbonate (3 eq), additive silver hexafluoroantimonate (0.5 eq), 1,2-bis(4-bromophenyl)acetylene (1.0 eq). This mixture was stirred at room temperature for one hour and then heated to reflux overnight. The reaction was detected by thin plate chromatography, and after cooling, the reaction was cooled to room temperature. The reaction was quenched with water and extracted 4×20 mL with dichloromethane. Wash with saturated brine, dry over anhydrous sodium sulfate, and remove sodium sulfate by filtration. The solvent was evaporated under reduced pressure to give a crude material. Using petroleum ether/ethyl acetate as the eluent, Purified by column chromatography (mobile phase: ethyl acetate/petroleum ether = 1/3) a pale yellow solid product was obtained in a yield of 47%.
  • 63
  • [ 1187-59-3 ]
  • [ 2789-89-1 ]
  • 3,4,7,8-tetrakis(4-bromophenyl)-2,6-dimethyl-2,6-dihydro-2,6-naphthyridin-1,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With dirhodium tetraacetate; silver hexafluoroantimonate; silver carbonate; In toluene; at 20℃;Reflux; The preparation method is as follows: A toluene solution of <strong>[1187-59-3]N-<strong>[1187-59-3]methyl acrylamide</strong></strong> was added to a clean 30 mL round bottom flask containing stirring magnets at a concentration of 1 M. Then add the catalyst cerium acetate (10 mol%), the oxidant silver carbonate (3 eq), Additive silver hexafluoroantimonate (0.5 eq), 1,2-bis(4-bromophenyl)acetylene (1.0 eq). This mixture was stirred at room temperature for one hour and then heated to reflux overnight. The reaction was detected by thin plate chromatography, and after cooling, the reaction was cooled to room temperature. The reaction was quenched with water and extracted 4×20 mL with ethyl acetate. Washed with saturated saline, Dry over anhydrous sodium sulfate and remove sodium sulfate by filtration. The solvent was evaporated under reduced pressure to give a crude material. Using petroleum ether/ethyl acetate as the eluent, Purified by column chromatography (mobile phase: ethyl acetate / petroleum ether = 1/2) A pale yellow solid product was obtained in a yield of 52%.
  • 64
  • [ 2244-16-8 ]
  • [ 2789-89-1 ]
  • (1S,4R)-7,8-bis(4-bromophenyl)-1-methyl-4-(prop-1-en-2-yl)bicyclo[4.2.0]oct-7-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In ethyl acetate at 20℃; Schlenk technique; Inert atmosphere; Irradiation; 6.6 Preparation and Characterization of Products General procedure: The photocatalyst [Ir(dF-CF3-ppy)2(dtbpy)]PF6 (PC-1) (11.2 mg, 0.01 mmol, 2.0 mol%) wasadded to an oven-dried Schlenk tube containing a magnetic stirring bar and anhydrous ethylacetate (2.5 mL, 0.2 M) was added under argon. In the absence of light, the enone (0.5 mmol,1.0 equiv) and the alkyne (1.0 mmol, 2.0 equiv) were added under an argon stream. Theresulting solution was degassed using three freeze-pump-thaw cycles and the tube was finallybackfilled with argon. The reaction mixture was allowed to stir at room temperature for 24 hunder irradiation with visible light from two 30 W Kessil LEDs (λmax = 455 nm, see chapter 1.2).The solvent was evaporated and the crude reaction products were purified by columnchromatography over silica gel (dry load of crude material, pentane/EtOAc or pentane/diethylether mixtures as eluent) to afford products 6a-6e, 9a-9e and 10.
  • 66
  • [ 2789-89-1 ]
  • [ 15754-60-6 ]
  • (Z)-1-(4,5-bis(4-bromophenyl)-2-methylpent-4-en-2-yl)-1H-pyrazole [ No CAS ]
  • 67
  • [ 13515-65-6 ]
  • [ 2789-89-1 ]
  • 4,5-bis(4-bromophenyl)-2-isopropylthiazole [ No CAS ]
  • 68
  • [ 2789-89-1 ]
  • N-((1-cyclohexyl-1H-tetrazol-5-yl)methyl)benzamide [ No CAS ]
  • 3,4-bis(4-bromophenyl)-2-((1-cyclohexyl-1H-tetrazol-5-yl)methyl)isoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; copper diacetate In tert-Amyl alcohol at 120℃; for 12h; Sealed tube; General procedure B for the rhodium catalyzed addition of diphenylacetylenes to acylated α-aminotetrazole General procedure: The N-acylated aminomethyltetrazole (0.25 mmol, 1.0 equiv),arylacetylene (0.375 mmol, 1.5 equiv), Cu(OAc)2 (0.5 mmol,2.0 equiv), CsOAc (0.125 mmol, 0.5 equiv) and [RhCp*Cl2]2(0.0125 mmol, 5 mol %) were suspended in t-AmOH (1.5 mL,0.17 M) in a sealed tube containing a magnetic stirring bar. Themixture was reacted under conventional heating in an oil bath at120 °C for 12 h. After completion of the reaction (checked byTLC), the mixture was diluted with AcOEt (10 mL), filteredthrough a Celite pad and washed with additional AcOEt(10 mL). Then the solvent was removed under reduced pressureand the reaction crude was purified by LCC to get the titlecompound.
  • 69
  • [ 2789-89-1 ]
  • [ 291514-02-8 ]
  • 4,5-bis(4-bromophenyl)-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]isothiazole 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; acetic acid In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; diastereoselective reaction;
  • 70
  • [ 2789-89-1 ]
  • [ 245368-50-7 ]
  • 5,6-bis(4-bromophenyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c][1,2]thiazine 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; trifluoroacetic acid In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; diastereoselective reaction;
  • 71
  • [ 2789-89-1 ]
  • [ 100-51-6 ]
  • [ 36741-17-0 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1,2-bis(4-bromophenyl)acetylene; benzyl alcohol With iodine; dimethyl sulfoxide at 130℃; for 24h; Green chemistry; Stage #2: With ammonium acetate In ethanol at 100℃; for 2h; Green chemistry; 4.1 General procedure for the synthesis 2,4,5-trisubstituted imidazoles (3) General procedure: Alkyne (0.5 mmol, 1 equiv.), primary alcohol (0.5 mmol, 1 equiv.), I2 (1 mmol, 253.8 mg, 2 equiv.) and DMSO (2 mL) were mixed in a round bottom flask and heated at 130 °C for 24 h. Thereafter, ammonium acetate (5 mmol, 385.4 mg, 10 equiv.) and EtOH (2 mL) was added to the mixture and heated at 100 °C for 2 h. After cooling, a solution of 1% Na2S2O3 was added dropwise to the mixture to form a precipitate which was filtered and dried. The crude product was recrystallized from EtOH to afford spectroscopically pure imidazole 3.
  • 72
  • [ 52260-22-7 ]
  • [ 2789-89-1 ]
  • [ 1314243-16-7 ]
YieldReaction ConditionsOperation in experiment
71% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; sodium acetate In ethanol at 60℃; for 12h; Inert atmosphere; Green chemistry; To a 13 × 150 mm test tube equipped with magnetic stir bar were added [RhCp*(CH3CN)3](SbF6)2 (6.6mg, 4 mol %), NaOAc (32.8mg, 0.4 mmol, 2 equiv) and 2a-2o (0.3 mmol, 1.5 equiv). The test tube was sealed with a rubber septum and removed from the glove-box. The solution of 1a-1r (0.2 mmol, 1 equiv)in EtOH (2 mL) was injected into the test tube via syringe. The reaction mixture was placed in a preheated oil bath (60 ) for 12 h. Then the reaction mixture was concentrated in vacuo, the residue was dissolved in methylene chloride and purified by column chromatography (silica gel, n-hexane/EtOAc =20/1). 1-Methyl-3,4-diphenylisoquinoline (3aa): The title compound was obtained as white crystal in 91% yield (54.2 mg). 1H NMR (400 MHz, CDCl3) δ 8.24 - 8.16(m, 1H), 7.66 (m, 1H), 7.63 - 7.55 (m, 2H), 7.41 - 7.28 (m, 5H), 7.26 - 7.12 (m,5H), 3.09 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 157.78, 149.37, 140.90, 137.56,136.06, 131.44, 130.32, 130.04, 129.29, 128.24, 127.66, 127.18, 127.01, 126.62,126.29, 126.19, 125.60, 22.73. HRMS (EI) calcd. for C22H17N: [M]+, 295.1361. Found: m/z 295.1358.
  • 73
  • [ 2789-89-1 ]
  • [ 54015-96-2 ]
  • 5,6,7,8-tetrakis(4-bromophenyl)-3-methoxy-1-(pyridin-2-yl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium acetate In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; Inert atmosphere;
  • 74
  • [ 2789-89-1 ]
  • [ 10172-51-7 ]
  • [ 2966-50-9 ]
  • C31H24Br2NO2(1+)*C2F3O2(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In ethanol at 80℃; for 0.5h; Inert atmosphere; 19 The 6,7-dimethoxy 1-phenyl-3,4-dihydroisoquinol 1c (133.7mg, 0.5mmol),1,2-bis(4-bromophenyl)acetylene 2d (168.0mg, 0.5mmol),Dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer [(Cp*RhCl2)2, 1.05mg, 0.5%mmol], AgOOCCF3(165.6mg, 0.75mmol) and Cu(OAc)2 (90.8mg, 0.5mmol) was added to a 25mL round bottom flask, and then 5mL of absolute ethanol was added.The reaction was stopped after heating and refluxing for 30 minutes under the protection of N2, and filtered with 100-200 mesh silica gel and washed with ethanol.Collect the organic phase and distill under reduced pressure to remove the organic solvent. The residue is separated and purified by 200-300 mesh silica gel column chromatography.Elute with dichloromethane/methanol=20:1 (V/V) to obtain 336.2 mg of pure trifluoroacetate dihydroisoquinoline derivative 3dc.The product was a bright yellow solid with a yield of 94%.
  • 75
  • [ 19712-49-3 ]
  • [ 2789-89-1 ]
  • [ 2966-50-9 ]
  • C30H22Br2NO(1+)*C2F3O2(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In ethanol at 80℃; for 0.5h; Inert atmosphere; 14 The 6-methoxy 1-phenyl-3,4-dihydroisoquinol 1b (118.7 mg, 0.5 mmol),1,2-bis(4-bromophenyl)acetylene 2d (168.0mg, 0.5mmol),Dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer [(Cp*RhCl2)2, 1.05mg, 0.5%mmol], AgOOCCF3(165.6mg, 0.75mmol) and Cu(OAc)2 (90.8mg, 0.5mmol) was added to a 25mL round bottom flask,Then add 5 mL of absolute ethanol.The reaction was stopped after heating and refluxing for 30 minutes under the protection of N2, and filtered with 100-200 mesh silica gel and washed with ethanol.The organic phase was collected, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by 200-300 mesh silica gel column chromatography, eluted with dichloromethane/methanol=20:1 (V/V)315.2mg of pure trifluoroacetate dihydroisoquinol salt derivative 3db is obtained.The product is a yellow solid with a yield of 92%.
  • 76
  • [ 2789-89-1 ]
  • [ 3375-31-3 ]
  • [ 107-06-2 ]
  • [ 1527-91-9 ]
  • ((1Z,3Z)-4-(2-(((Z)-amino(phenyl)methylene)amino)phenyl)-1,2,3,4-tetrakis(4-bromophenyl)buta-1,3-dien-1-yl)palladium(II) chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tetrabutyl ammonium fluoride In isopropyl alcohol; toluene at 80℃; for 48h; 2. General Procedure for C-H Activation/Insertion CascadeReactions General procedure: A mixture of Pd(OAc)2 (0.0445 mmol), Bu4NF (0.25 mmol, 44.0 uL), amidine 1a-1w (0.125mmol), alkyne 2a-2m (0.125 mmol), iPrOH (0.375 mmol, 29 uL), and toluene/DCE= 0.4:1.6 (2mL) was stirred at 80 C for 48 h. After cooling the reaction to room temperature, the solvent was removed under vacuum and the residue was purified by silica gel chromatography using petroleumether/ethyl acetate = 8:1~6:1 to afford desired products.
  • 77
  • [ 2789-89-1 ]
  • 3,3-dimethyl-2-(pyridin-2-yl)isoindolin-1-one [ No CAS ]
  • 3,3-dimethyl-2-(5,6,7,8-tetrakis(4-bromophenyl)isoquinolin-1-yl)isoindolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; silver(I) acetate In 1,2-dichloro-ethane at 100℃; for 24h; Schlenk technique; Isoquinolines 3 via Oxidative Annulation of Directing Group Sub-stituted Pyridines 1 with Alkynes 2; General Procedure General procedure: A 25 mL Schlenk tube was charged with 1 (0.2 mmol, 1.0 equiv), 2(0.48 mmol, 2.4 equiv), Cp*Rh(CH 3 CN) 3 (SbF 6 ) 2 (5 mol%), and AgOAc(2.2 equiv) in DCE (1 mL). The mixture was stirred at 100 °C for 24 h.After cooling to room temperature, the reaction mixture was directlyloaded onto a silica gel column which was then eluted with petroleumether/ethyl acetate (PE/EA, v/v) to afford the desired 3.
78% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; silver(I) acetate In 1,2-dichloro-ethane at 150℃; for 12h; 6 Synthesis of 3,3-dimethyl-2-(5,6,7,8-tetra(4-bromophenyl)-1-isoquinolinyl)isoindol-1-one (R = 4-bromophenyl): In a 25 ml Young’s tube, add 3,3-dimethyl-2-pyridylisoindol-1-one (1 mmol), 1,2-bis(4-fluorobenzene)acetylene (2.4 mmol), Cp*Rh(CH3CN)3(SbF6)2 (1mol%) and silver acetate (1mmol), finally add 5mL of 1,2-dichloroethane solvent to the reaction tube, and react at 150 for 12 After the reaction is over, the reaction solution is cooled to room temperature, and the organic solvent is removed under reduced pressure to obtain the crude product, which is further separated by silica column chromatography and eluted with petroleum ether/ethyl acetate (volume ratio: 10/1) to obtain the pure product 3,3-Dimethyl-2-(5,6,7,8-tetra(4-bromophenyl)-1-isoquinolinyl)isoindol-1-one, the yield is 78%.
  • 78
  • [ 2789-89-1 ]
  • [ 13885-09-1 ]
  • (E)-(2'-(1,2-bis(4-bromophenyl)vinyl)-[1,1'-biphenyl]-2-yl)diphenylphosphane [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium pivalate In dichloromethane at 100℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; (2′-Alkenylbiaryl-2-yl)(diphenyl)phosphines 3aa-da; GeneralProcedure A General procedure: In an oven-dried 25-mL Schlenk tube with a Teflon screw cap,the appropriate diarylphosphine 1 (0.20 mmol, 1.0 equiv),alkyne 2 (0.20 mmol, 1.0 equiv), [Rh(COD)Cl]2 (4.9 mg, 0.01mmol, 5 mol%), and NaOPiv (49.6 mg, 0.40 mmol, 2.0 equiv)were dissolved in CH2Cl2 (2.0 mL) under N2. The mixture wasstirred at 100 °C for 12 h until the starting material was completelyconsumed (TLC), then cooled to r.t. The solvent wasremoved and the residue was directly purified by column chromatography(silica gel).
  • 79
  • [ 2789-89-1 ]
  • [ 67-64-1 ]
  • [ 191666-53-2 ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 1,2-bis(4-bromophenyl)acetylene With diiron nonacarbonyl; potassium <i>tert</i>-butylate In tetrahydrofuran at 75℃; for 12h; Inert atmosphere; Stage #2: acetone With copper(II) choride dihydrate In tetrahydrofuran Inert atmosphere; General procedure for the synthesis of cyclobutenedione General procedure: THF (150 mL) was addedto a mixture of Fe2(CO)9 (5.457 g, 15.00 mmol) and t-BuOK (2.245 g, 20.00 mmol) at roomtemperature under argon. The resulting mixture was stirred for 0.5 h at room temperatureand another 15 min at 65 °C. Diphenylacetylene (0.892 g, 5.00 mmol) was added andthen further stirred for 12 h at 75 °C. The mixture was cooled to room temperature,and CuCl2*2H2O (12.786 g, 75.00 mmol) in acetone (50 mL) was added. After filtration,the filtrate was concentrated under reduced pressure. The residue was purified by flashchromatography (petrol ether/EtOAc = 20:1) to give products. TheNMRdata are consistentwith previous reports in the literature (1a [32,37], 1b, 1d, 1f-1h [37], 1e [38]).
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