Name: 42472-69-5|1-(4-Ethynylphenyl)ethanone|95%
Brand: Ambeed
SKU: A660492
Price: 10.0 USD
Availability: InStock
Rating: 99 (25 reviews)

1
[ 75883-03-3 ]
[ 42472-69-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In methanol at 20℃; for 0.25h;	2.2 Synthesis of Compound 2 Dissolve 1.0 g of Compound 1 (5.04 mmol) and 690 mg of potassium carbonate (5.04 mmol) in 40 mL of methanol, and stir at room temperature for 15 minutes. The reaction solution is a mixture of dichloromethane and water (such as the volume of dichloromethane and water) (A mixed solution with a ratio of 1: 1) was extracted twice, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 666 mg of Compound 2 (yellow solid, yield 100%).
100%	With methanol; potassium carbonate at 20℃; for 0.25h;
97%	With aluminum(III) oxide; potassium fluoride for 0.05h; microwave irradiation;

97%	With potassium fluoride In methanol at 20℃; for 12h;
95%	With methanol; potassium hydroxide at 10 - 20℃; for 1h;	To a stirring solution of compound 1.9 (19 gs 88 rnrnoi) in MeOH (200 mL) was added a solution of KOH (2.46 g, 44 mrnoi) in MeOH (20 mL) at 10°C and the mixture was stirred at room temperature for 1 hr. AeOH was added until the pH was 7. and the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), washed with 5% aqueous NaHCOa (100 mL), brine (1 Q0 mL), dried, and concentrated under reduced pressure to give compound 1.10 as a white solid (12 g, 95%). 1H N R (400 MHz, DMSO-efe) δ 7.95 (d, J = 8, 2H), 7.82 (d, J = 8, 2H), 4.49 (s, 1 H), 2.59 (s, 3 M),
91%	With potassium carbonate In methanol at 25℃; for 3h;
91%	With potassium carbonate In methanol at 20℃; for 1h;	8.2 Synthesis of 1-(4-ethynylphenyl)ethanone l-(4-((trimethylsilyl)ethynyl)phenyl)ethanone (0.86 g, 4.0 mmol), potassium carbonate (1.1 g, 8.0 mmol), and methanol (8 mL) were reacted at room temperature for 1 hour. After the solvent was distilled off under reduced pressure, water was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with water and brine, and anhydrous sodium sulfate was added to dry the layer. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure and the residue was purified by flash chromatography to obtain 1-(4-ethynylphenyl)ethanone (0.53 g; yield, 91%).
88%	With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere; Schlenk technique;
85%	With potassium hydroxide In methanol for 1h; Ambient temperature;
85%	With sodium hydroxide In methanol; diethyl ether at 20℃; for 0.166667h;
68%	With potassium carbonate In methanol; lithium hydroxide monohydrate at 20℃;
32%	With potassium carbonate In methanol at 25℃; for 6h;
	With sodium hydroxide; dibenzo-18-crown-6 In tetrahydrofuran; ethanol at 50℃; for 3h;
	With potassium carbonate In methanol at 20℃; for 2h;
	With methanol; potassium carbonate In dichloromethane at 20℃; for 2h; Inert atmosphere;
0.69 g	With potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere;
1.3 g	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;
6.2 g	With potassium fluoride In tetrahydrofuran; methanol at 25℃; for 0.5h;
1.06 g	With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
89 %Chromat.	With anhydrous potassium trimethylsilanolate In dimethyl sulfoxide at 70℃; for 6h; Sealed tube; Schlenk technique;
	With copper (I) iodide; hydrofluorosilicic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; lithium hydroxide monohydrate at 60℃; for 2h;
0.52 g	With methanol; sodium hydroxide In diethyl ether at 20℃; for 0.25h;
	With potassium fluoride In methanol at 20℃; for 24h; Sealed tube;
	With methanol; potassium carbonate at 25℃; for 1.5h; Inert atmosphere;
	With potassium carbonate In methanol at 20℃;
2.47 g	With methanol; potassium carbonate at 20℃; for 24h;	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%).

Reference： [1]Current Patent Assignee: GUANGZHOU UNIVERSITY OF CHINESE MEDICINE - CN111072466, 2020, A Location in patent: Paragraph 0070-0071; 0074-0075
[2]Chen, Huihong; Huang, Xin-An; Liang, Yunshi; Wu, Haiting; Xiang, Lingling; Zhang, Jing; Zhao, Hailong [Organic and biomolecular chemistry, 2020, vol. 18, # 27, p. 5120 - 5124]
[3]Kabalka, George W.; Zhou, Li-Li; Wang, Lei; Pagni, Richard M. [Tetrahedron, 2006, vol. 62, # 5, p. 857 - 867]
[4]Xu, Caixia; Du, Weiyuan; Zeng, Yi; Dai, Bin; Guo, Hao [Organic Letters, 2014, vol. 16, # 3, p. 948 - 951]
[5]Current Patent Assignee: ACHAOGEN INC - WO2013/170165, 2013, A1 Location in patent: Page/Page column 90
[6]Wang, Yue; Huang, Bin; Sheng, Shouri; Cai, Mingzhong [Journal of Chemical Research, 2007, # 12, p. 728 - 732]
[7]Current Patent Assignee: ISHIHARA SANGYO KAISHA, LTD. - WO2014/98259, 2014, A1 Location in patent: Page/Page column 38; 39
[8]Pan, Shitao; Xie, Qiqiang; Wang, Xiu; Wang, Qian; Ni, Chuanfa; Hu, Jinbo [Chemical Communications, 2022, vol. 58, # 33, p. 5156 - 5159]
[9]Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. [Synthesis, 1980, # 8, p. 627 - 630]
[10]Feng, Yi-Si; Xie, Chuan-Qi; Qiao, Wen-Long; Xu, Hua-Jian [Organic Letters, 2013, vol. 15, # 4, p. 936 - 939]
[11]Ikeda, Akari; Omote, Masaaki; Kusumoto, Kana; Tarui, Atsushi; Sato, Kazuyuki; Ando, Akira [Organic and Biomolecular Chemistry, 2015, vol. 13, # 33, p. 8886 - 8892]
[12]Zimin, Dmitry P.; Dar'in, Dmitry V.; Eliseeva, Anastasiya A.; Novikov, Alexander S.; Rassadin, Valentin A.; Kukushkin, Vadim Yu. [European Journal of Organic Chemistry, 2019, vol. 2019, # 35, p. 6094 - 6100]
[13]Khotina, Irina A.; Shmakova, Olga E.; Baranova, Diana Yu.; Burenkova, Natalia S.; Gurskaja, Anastasia A.; Valetsky, Peter M.; Bronstein, Lyudmila M. [Macromolecules, 2003, vol. 36, # 22, p. 8353 - 8360]
[14]Yu, Robert T.; Rovis, Tomislav [Journal of the American Chemical Society, 2006, vol. 128, # 38, p. 12370 - 12371]
[15]Miersch, Anne; Hilt, Gerhard [Chemistry - A European Journal, 2012, vol. 18, # 32, p. 9798 - 9801]
[16]Shao, Xinxin; Wang, Xueqiang; Yang, Tao; Lu, Long; Shen, Qilong [Angewandte Chemie - International Edition, 2013, vol. 52, # 12, p. 3457 - 3460][Angew. Chem., 2013, vol. 125, # 12, p. 3541 - 3544,4]
[17]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]
[18]Lin, Yuanguang; Song, Qiuling [European Journal of Organic Chemistry, 2016, vol. 2016, # 18, p. 3056 - 3059]
[19]Jordan, Robert S.; Li, Yolanda L.; Lin, Cheng-Wei; McCurdy, Ryan D.; Lin, Janice B.; Brosmer, Jonathan L.; Marsh, Kristofer L.; Khan, Saeed I.; Houk; Kaner, Richard B.; Rubin, Yves [Journal of the American Chemical Society, 2017, vol. 139, # 44, p. 15878 - 15890]
[20]Roy, Satyajit; Das, Sandip Kumar; Chattopadhyay, Buddhadeb [Angewandte Chemie - International Edition, 2018, vol. 57, # 8, p. 2238 - 2243][Angew. Chem., 2018, vol. 130, # 8, p. 2260 - 2265,6]
[21]Yao, Wubing; Li, Rongrong; Jiang, Huajiang; Han, Deman [Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2250 - 2255]
[22]Lasányi, Dániel; Tolnai, Gergely L. [Organic Letters, 2019, vol. 21, # 24, p. 10057 - 10062]
[23]Liu, Lang; She, Mengyao; Zhang, Jun; Wang, Zhaohui; Liu, Hua; Tang, Mi; Liu, Ping; Zhang, Shengyong; Li, Jianli [Green Chemistry, 2020, vol. 22, # 10, p. 3111 - 3116]
[24]Varga, Bálint; Tóth, Balázs L.; Béke, Ferenc; Csenki, János T.; Kotschy, András; Novák, Zoltán [Organic Letters, 2021, vol. 23, # 12, p. 4925 - 4929]
[25]Ming, Xiao-Xia; Wu, Shuai; Tian, Ze-Yu; Song, Jia-Wei; Zhang, Cheng-Pan [Organic Letters, 2021, vol. 23, # 17, p. 6795 - 6800]
[26]Zhang, Yu-Yang; Li, Han; Jiang, Xiaoding; Subba Reddy, Chitreddy V; Liang, Hao; Zhang, Yaqi; Cao, Rihui; Sun, Raymond Wai-Yin; Tse, Man Kin; Qiu, Liqin [Advanced Synthesis and Catalysis, 2022, vol. 364, # 3, p. 525 - 530]
[27]Kumaki, Wataru; Kinoshita, Hidenori; Miura, Katsukiyo [Tetrahedron, 2022, vol. 110]

2
[ 95785-28-7 ]
[ 42472-69-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With aluminum oxide; potassium hydroxide for 0.00694444h; microwave irradiation;
78%	With 18-crown-6 ether; potassium carbonate In toluene at 120℃; for 8h;
56%	With sodium hydroxide In toluene at 120℃; for 0.25h;	44.2 1.45 g (7.17 mmol) of dimethylhydroxymethyl-4-acetylphenylacetylene and 301 mg (7.53 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98 %) were placed in a 100 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 36 mL of toluene was added thereto and the mixture was refluxed at 120°C for 15 minutes. Toluene was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure by an evaporator. Then, 25 mL of hexane was added to the resulting crude reaction product and the mixture was cooled to give 4-acetylphenylethyne as a yellow solid. (0.74 g; yield: 56%). 1H-NMR (300 MHz, CDCl3) δ: 7.88-7.94 (m, 2H), 7.53-7.59 (m, 2H), 3.25 (s, 1H), 2.60 (s, 3H) [MS] EI (m/z): 144(M+-1), CI (m/z): 145 (MH+)

51%	With sodium hydride In toluene at 110℃;
	With 18-crown-6 ether; potassium carbonate In toluene for 8h; Heating;

Reference： [1]Pourjavadi, Ali; Bagheri Marandi, Gholam [Journal of Chemical Research - Part S, 2002, # 11, p. 552 - 555]
[2]Gallagher, William P.; Maleczka Jr., Robert E. [Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6775 - 6779]
[3]Current Patent Assignee: UBE INDUSTRIES LIMITED - EP1847545, 2007, A1 Location in patent: Page/Page column 55
[4]Havens, Stephen J.; Hergenrother, Paul M. [Journal of Organic Chemistry, 1985, vol. 50, # 10, p. 1763 - 1765]
[5]Gallagher, William P.; Maleczka Jr., Robert E. [Synlett, 2003, # 4, p. 537 - 541]

3
[ 42472-69-5 ]
[ 210106-54-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-chloro-succinimide; anhydrous sodium carbonate; silver(I) nitrate In propan-2-one at 50℃; for 8h; Schlenk technique;
30%	With N-chloro-succinimide; n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;

Reference： [1]Hu, Jinhui; Huang, Yubing; Ji, Xiaoliang; Jiang, Huanfeng; Li, Yibiao; Nie, Jinli; Peng, Xin; Xu, Xuetao [Organic Letters, 2022]
[2]Nishihara, Yasushi; Ikegashira, Kazutaka; Hirabayashi, Kazunori; Ando, Jun-Ichi; Mori, Atsunori; Hiyama, Tamejiro [Journal of Organic Chemistry, 2000, vol. 65, # 6, p. 1780 - 1787]

4
[ 591-50-4 ]
[ 42472-69-5 ]
[ 1942-31-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With palladium(II) oxide; triethylamine In water at 80℃; for 6h;
99%	With triethylamine In water at 80℃; for 6h;
96%	With copper(l) iodide; triethylamine; triphenylphosphine In water at 60℃; for 24h; Schlenk technique; Inert atmosphere;	2.4 Catalysis General procedure: Sonogashira reactions. Typically, a mixture of aryl halide (0.2 mmol), Pd/MPC (2 mg, 0.004 mmol Pd), and CuI(0.02 mmol) and PPh3 (0.02 mmol) were added together into a Schlenk tube, and then terminal alkyne (0.4 mmol), NEt3 84 μL (0.6 mmol) and H2O 2 mL were added under N2 atmosphere. The mixture was heated in oil bath at 60 °C under stirring for 24 h. The reaction product was monitored by TLC and GC. Target product was isolated and purified by column chromatography, and the yields ofproduct were calculated on the basis of theoretical yield of aryl halide. The identification of product was conducted by NMR measurements on VNMRS 600 spectrometer. For recycling, the Sonogashira reaction was conducted with 4-nitrobromobenzene and phenylacetylene maintaining the same reaction conditions except using the recovered catalyst. The Pd/MPC was recovered by simple filtration, and then it was washed with ethanol and H2O thoroughly. The recovered catalyst was dried at 80 °C for the night and reuse in the next runs.

93%	With copper(l) iodide; palladium; triphenylphosphine for 0.0416667h; microwave irradiation;
67%	With di(pyridin-2-yl)amine; diamminedichloropalladium(II); triethylamine In water at 25℃; for 6h; Inert atmosphere;
	With copper(l) iodide; tri-1-napthylphosphine; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 14.5h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Teratani, Takuto; Ohtaka, Atsushi; Kawashima, Takahiro; Shimomura, Osamu; Nomura, Ryôki [Synlett, 2010, # 15, p. 2271 - 2274]
[2]Location in patent: experimental part Ohtaka, Atsushi; Teratani, Takuto; Fujii, Ryohei; Ikeshita, Kanako; Kawashima, Takahiro; Tatsumi, Koichi; Shimomura, Osamu; Nomura, Ryoki [Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 4052 - 4060]
[3]Wang, Peng; Wang, Guang-Yu; Qiao, Wen-Long; Feng, Yi-Si [Catalysis Letters, 2016, vol. 146, # 9, p. 1792 - 1799]
[4]Kabalka, George W.; Wang, Lei; Pagni, Richard M. [Tetrahedron, 2001, vol. 57, # 38, p. 8017 - 8028]
[5]Zhong, Hong; Wang, Jinyun; Li, Liuyi; Wang, Ruihu [Dalton Transactions, 2014, vol. 43, # 5, p. 2098 - 2103]
[6]Govdi, Anastasiya I.; Vasilevsky, Sergey F.; Malysheva, Svetlana F.; Kazheva, Olga N.; Dyachenko, Oleg A.; Kuimov, Vladimir A. [Heteroatom Chemistry, 2018, vol. 29, # 4]

5
[ 42472-69-5 ]
[ 132559-91-2 ]
4-(4'-acetylphenylethynyl)-6-methyl-2-pyrone [ No CAS ]

Reference： [1]Synthesis,2003,p. 2564 - 2570
[2]Tetrahedron Letters,2002,vol. 43,p. 8853 - 8857

6
[ 533-58-4 ]
[ 42472-69-5 ]
[ 132932-61-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	With caesium carbonate In toluene at 110℃; for 24h;
69%	With caesium carbonate In toluene at 110℃; for 24h;

Reference： [1]Saejueng, Pranorm; Bates, Craig G.; Venkataraman [Synthesis, 2005, # 10, p. 1706 - 1712]
[2]Bates, Craig G.; Saejueng, Pranorm; Murphy, Jaclyn M.; Venkataraman [Organic Letters, 2002, vol. 4, # 26, p. 4727 - 4729]

7
[ 42472-69-5 ]
[ 93131-74-9 ]
[ 123770-67-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With polymethylhydrosiloxane; cesium fluoride; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 20℃; for 6h;
91%	With polymethylhydrosiloxane; cesium fluoride; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 25℃; for 6h;

Reference： [1]Gallagher, William P.; Maleczka Jr., Robert E. [Synlett, 2003, # 4, p. 537 - 541]
[2]Gallagher, William P.; Maleczka Jr., Robert E. [Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6775 - 6779]

8
[ 42472-69-5 ]
[ 64-19-7 ]
Acetic acid (1E,3E)-1,4-bis-(4-acetyl-phenyl)-buta-1,3-dienyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) In 1,4-dioxane at 20℃; for 2h;

Reference： [1]Le Paih, Jacques; Monnier, Florian; Derien, Sylvie; Dixneuf, Pierre H.; Clot, Eric; Eisenstein, Odile [Journal of the American Chemical Society, 2003, vol. 125, # 39, p. 11964 - 11975]

9
[ 31930-36-6 ]
[ 42472-69-5 ]
5-(4-acetylphenyl)pent-2-en-4-ynoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In toluene at 110℃; for 8h;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃;

Reference： [1]Bates, Craig G.; Saejueng, Pranorm; Venkataraman [Organic Letters, 2004, vol. 6, # 9, p. 1441 - 1444] Saejueng, Pranorm; Bates, Craig G.; Venkataraman [Synthesis, 2005, # 10, p. 1706 - 1712]
[2]Wang, Min; Liu, Zheng-Li; Zhang, Xiang; Tian, Pan-Pan; Xu, Yun-He; Loh, Teck-Peng [Journal of the American Chemical Society, 2015, vol. 137, # 47, p. 14830 - 14833]

10
[ 7511-49-1 ]
[ 42472-69-5 ]
[ 627911-42-6 ]

Reference： [1]Macromolecules,2003,vol. 36,p. 8353 - 8360

11
[ 42472-69-5 ]
[ 4016-63-1 ]
8-(4-acetylphenylethynyl)guanosine [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3529 - 3533

12
[ 672299-20-6 ]
[ 42472-69-5 ]
2-[(4-acetylphenyl)ethynyl]-N⁶-methoxyadenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 8h;

Reference： [1]Volpini, Rosaria; Dal Ben, Diego; Lambertucci, Catia; Taffi, Sara; Vittori, Sauro; Klotz, Karl-Norbert; Cristalli, Gloria [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1222 - 1230]

13
[ 934471-73-5 ]
[ 42472-69-5 ]
2-[(4-acetylphenyl)ethynyl]-N⁶-methoxy-5'-N-ethylcarboxamidoadenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 5h;

Reference： [1]Volpini, Rosaria; Dal Ben, Diego; Lambertucci, Catia; Taffi, Sara; Vittori, Sauro; Klotz, Karl-Norbert; Cristalli, Gloria [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1222 - 1230]

14
[ 42472-69-5 ]
[ 1079-66-9 ]
[ 935550-35-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In toluene at 80℃; for 4h;

Reference： [1]Kondoh, Azusa; Yorimitsu, Hideki; Oshima, Koichiro [Journal of the American Chemical Society, 2007, vol. 129, # 13, p. 4099 - 4104]

15
[ 934471-73-5 ]
[ 42472-69-5 ]
[ 536-74-3 ]
N⁶-methoxy-2-phenylethynyl-5'-N-ethylcarboxamidoadenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Volpini, Rosaria; Dal Ben, Diego; Lambertucci, Catia; Taffi, Sara; Vittori, Sauro; Klotz, Karl-Norbert; Cristalli, Gloria [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1222 - 1230]

16
[ 14243-64-2 ]
[ 42472-69-5 ]
4-acetylphenylethynyl(triphenylphosphine)gold [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium ethanolate; In ethanol; at 20℃; for 17h;	Under an argon atmosphere, Au(PPh3)Cl (297 mg, 0.60 mmol), 4-acetylphenylethyne (130 mg, 0.9 mmol) and ethanol (12 ml) were added to a 30 mL Schlenk tube, and then sodium ethoxide (247 µl, 0.63 mmol: 2.55 mol/L (liter) in ethanol solution) was added dropwise thereto and the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the resulting white precipitate was filtered and successively washed with ethanol (12 mlx three times), water (12 ml× three times) and ethanol (6 mlx three times), followed by drying under vacuum to give 0.32 g of the desired compound as a white powder (yield: 89%). 1H-NMR (300 MHz, CDCl3) δ: 7.84-7.88 (m, 2H), 7.43-7.61 (m, 17H), 2.57 (s, 3H) FAB-MS (M/Z): 603 (M+H)+ Luminescence analysis: (CHCl3, 77K, Ex250nm) λ (nm): 465, 499 Elemental analysis: Found C: 55.86, H: 3.67 Theoretical C: 55.83, H: 3.68

Reference： [1]Patent: EP1847545,2007,A1 .Location in patent: Page/Page column 55

17
[ 42472-69-5 ]
[ 217451-41-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium acetate; silver nitrate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 3h;
90%	With sodium carbonate; silver nitrate In acetonitrile at 50℃; for 2h;	2 Example 2 1 mmol of p-acetylphenylacetylene,0.01 mmol silver nitrate and0.5mmol sodium carbonate added to the market1 ml of acetonitrile in a round bottom flask,50 ° C for 2 hours.After completion of the reaction, the solid was removed by filtration,Column separation products, the yield of 90%.
83%	With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine In dichloromethane at 25℃;

82%	With copper(l) iodide; oxygen In acetonitrile at 20℃; for 15h; Irradiation; Green chemistry;
72%	With triethylamine In 1,4-dioxane Heating;
71%	With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; copper(l) iodide; diamminedichloropalladium(II); tetrabutylammomium bromide; triethylamine In water at 20℃; for 24h;
63%	With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; copper(ll) sulfate pentahydrate; iodine; potassium acetate In water at 120℃; for 24h;
50%	With oxygen In ethanol at 60℃; for 24h;
38%	With copper(I) oxide; tetrabutylammomium bromide; oxygen; sodium hydroxide In water at 80℃; for 24h; Green chemistry;
	With copper diacetate In pyridine; methanol for 2h; Heating;

Reference： [1]Mo, Guoli; Tian, Zaimin; Li, Jiping; Wen, Guohua; Yang, Xiaomin [Applied Organometallic Chemistry, 2015, vol. 29, # 4, p. 231 - 233]
[2]Current Patent Assignee: SHAOXING UNIVERSITY - CN104710254, 2017, B Location in patent: Paragraph 0029; 0030; 0031; 0032
[3]Jordan, Robert S.; Li, Yolanda L.; Lin, Cheng-Wei; McCurdy, Ryan D.; Lin, Janice B.; Brosmer, Jonathan L.; Marsh, Kristofer L.; Khan, Saeed I.; Houk; Kaner, Richard B.; Rubin, Yves [Journal of the American Chemical Society, 2017, vol. 139, # 44, p. 15878 - 15890]
[4]Sagadevan, Arunachalam; Charpe, Vaibhav Pramod; Hwang, Kuo Chu [Catalysis science and technology, 2016, vol. 6, # 21, p. 7688 - 7692]
[5]Kumar, Vipan; Chipeleme, Alex; Chibale, Kelly [European Journal of Organic Chemistry, 2008, # 1, p. 43 - 46]
[6]Location in patent: experimental part Chen, Shao-Nung; Wu, Wei-Yi; Tsai, Fu-Yu [Green Chemistry, 2009, vol. 11, # 2, p. 269 - 274]
[7]Location in patent: experimental part Wu, Tzu-Min; Huang, Shao-Hsien; Tsai, Fu-Yu [Applied Organometallic Chemistry, 2011, vol. 25, # 5, p. 395 - 399]
[8]Xu, Hang; Wu, Liangying; Tian, Jing; Wang, Jun; Wang, Peng; Niu, Xiyu; Yao, Xiaoquan [European Journal of Organic Chemistry, 2019, vol. 2019, # 39, p. 6690 - 6696]
[9]Tang, Bo-Xiao; Fang, Xiao-Niu; Kuang, Ren-Yun; Wu, Jian-Hong; Chen, Qiao; Hu, Shao-Jun; Liu, Yi-Lin [Applied Organometallic Chemistry, 2016, vol. 30, # 11, p. 943 - 945]
[10]Matsuda, Takanori; Kadowaki, Sho; Murakami, Masahiro [Chemical Communications, 2007, # 25, p. 2627 - 2629]

18
[ 935-14-8 ]
[ 1009-61-6 ]
[ 42472-69-5 ]

Yield	Reaction Conditions	Operation in experiment
18%; 65%	With water;methyl(triphenylphosphine)gold(I); sulfuric acid; In methanol; at 70℃; for 2h;	Example 46 To a solution in which 0.0024 g of methyl(triphenylphosphine)gold (0.005 mmol) was dissolved in 3 ml of methanol, 0.13 g of 1,4-diethynylbenzene (1 mmol) and an aqueous solution in which 0.05 g of concentrated sulfuric acid (0.5 mmol) was dissolved in 0.5 ml of water were added. After stirring at 70 C. for 2 hours, 4-ethynylacetophenone was obtained in 65% yield, and 1,4diacetylbenzene was obtained in 18% yield (catalyst turnover number: 202).

Reference： [1]Patent: US2005/143597,2005,A1 .Location in patent: Page/Page column 8
[2]Tetrahedron Letters,2014,vol. 55,p. 1608 - 1612
[3]Angewandte Chemie - International Edition,2010,vol. 49,p. 6813 - 6816

19
[ 1015419-79-0 ]
[ 42472-69-5 ]
C₂₃H₂₄N₂O₂ [ No CAS ]
[ 1015419-91-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	In toluene at 110℃; for 3h;

Reference： [1]Yu, Robert T.; Rovis, Tomislav [Journal of the American Chemical Society, 2008, vol. 130, # 11, p. 3262 - 3263]

20
[ 1214264-88-6 ]
[ 42472-69-5 ]
[ 1214264-95-5 ]
(CH₃)4C₂O₂BC(CH₃COC₆H₄)CHB(NH)2C₁₀H₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 2548 - 2549
[2]Journal of the American Chemical Society,2010,vol. 132,p. 2548 - 2549

21
[ 1214264-88-6 ]
[ 42472-69-5 ]
[ 1214264-95-5 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 2548 - 2549

22
[ 1315267-65-2 ]
[ 42472-69-5 ]
[ 1315267-69-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; trifuran-2-yl-phosphane; diisopropylamine; palladium dichloride In toluene at 55℃; Inert atmosphere; chemoselective reaction;	General procedure for chemoselective Sonogashira cross-coupling reaction of benzyl 5-bromo-2-iodophenylcarbamate (3) and arylalkynes (4a-o). General procedure: To a degassed solution of benzyl 5-bromo-2-iodophenylcarbamate 3 (0.50 mmol) and an arylalkyne 4 (0.52 mmol) in dry toluene (10.0 mL) under N2 was added diisopropylamine (0.60 mmol), palladium(II) chloride (0.03 mol), tri-2-furylphosphine (0.60 mol) and copper(I) iodide (0.03 mol). This mixture was stirred at 55 C. After completion of the reaction (typically less than 1 h) as indicated by TLC analysis, toluene was removed in vacuo and the residue was dissolved in dichloromethane and adsorbed on silica gel. After flash chromatography (SiO2-gel, elution with EtOAc/hexane gradient) the solid residue was dissolved in chloroform and petroleum ether was added to precipitate. Finally, the solid was triturated and washed with a chloroform/petroleum ether mixture to afford the desired pure product 5a-o.

Reference： [1]Valois-Escamilla, Ismael; Alvarez-Hernandez, Alejandro; Rangel-Ramos, Luis Felipe; Suárez-Castillo, Oscar Rodolfo; Ayala-Mata, Francisco; Zepeda-Vallejo, Gerardo [Tetrahedron Letters, 2011, vol. 52, # 29, p. 3726 - 3728]

23
[ 42472-69-5 ]
[ 829-31-2 ]
[ 1315168-25-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With palladium diacetate; copper dichloride; silver(l) oxide In toluene at 75℃; for 8h;	Representative procedure (Table 3, entry 1): To an oven-dried 10 mL round-bottom flask equipped with a stirrer bar was added 79 mg of 1a (0.4 mmol), followed by 4.8 mg of Pd(OAc)2 (0.021 mmol, 5 mol %), 6.0 mg of CuCl2 (0.045 mmol, 11 mol %), and 186 mg of Ag2O (0.8 mmol, 2.0 equiv). Toluene (2.5 mL) was added and the mixture was stirred at 75 °C while open to air. To this flask was added a solution containing 62 mg of 2a (0.6 mmol, 1.5 equiv) and another 4.8 mg of Pd(OAc)2 (0.021 mmol, 5 mol %) in 2.5 mL of toluene via syringe pump over 6 h. After complete addition, the reaction was continued for 2 h and judged complete by TLC. The mixture was then cooled to ambient temperature, filtered, and washed with EtOAc. The filtrate was washed once with brine and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and evaporated. The residue was purified by column chromatography (petroleum ether/EtOAc = 4:1), to afford 81 mg of 3aa (69%) as a brown solid.

Reference： [1]Location in patent: experimental part Wu, Chunrui; Li, Pan; Fang, Yuesi; Zhao, Jingjing; Xue, Weichao; Li, Yang; Larock, Richard C.; Shi, Feng [Tetrahedron Letters, 2011, vol. 52, # 29, p. 3797 - 3801]

24
[ 13329-40-3 ]
[ 471-25-0 ]
[ 42472-69-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 0 - 60℃; for 5h; Sealed flask;	21. Typical experimental procedure: General procedure: Method B; Pd(PPh3)2Cl2 (35.1 mg, 0.05 mmol), 1,4-bis(diphenylphosphino)butane (42.6 mg, 0.1 mmol), Cu(acac)2 (52.4 mg, 0.2 mmol), aryl halides (2.0 mmol), and DBU (1.52 g, 10.0 mmol) were combined with DMSO (4.0 mL), in a small round-bottomed flask. Propiolic acid (1a) (140.0 mg, 2.0 mmol) was dropped at 0-5 °C, and the flask was sealed with a septum. The resulting mixture was stirred at 25 °C for 5 h. Then the reaction temperature was increased to 60 °C, and the mixture was stirred for 6 h. The reaction was poured into Ethyl acetate and washed with water saturated by NH4Cl. The organic layer dried over MgSO4, and filtered. The solvent was removed under vacuum, and the resulting crude product was purified by flash chromatography on silica gel to give 4a (230.9 mg, 79% yield). The spectroscopic data of 4a-j are as follows.

Reference： [1]Location in patent: experimental part Park, Kyungho; Palani, Thiruvengadam; Pyo, Ayoung; Lee, Sunwoo [Tetrahedron Letters, 2012, vol. 53, # 7, p. 733 - 737]

25
[ 42472-69-5 ]
[ 10537-63-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 40℃; for 5h; Inert atmosphere;
90%	With water; zinc(II) iodide; zinc In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	20 Example 20 In an anhydrous and oxygen-free glove box under an argon atmosphere, add ZnI2 (0.01mmol), Zn (0.3mmol) and 4-ethynylacetophenone (0.2mmol) to a 10mL reaction tube, and then add 2ml DMF (N,N-dimethylformamide), then add water (1.0mmol) and send it out of the glove box. The reaction was carried out in an oil bath at 90, and the progress of the reaction was monitored by TLC monitoring and I2 color development. After the reaction was completed, the organic phase was extracted and concentrated by adding water, and the column was passed through silica gel to obtain a styrene compound as a colorless liquid. The yield was 90% .
89%	With water; zinc(II) iodide; zinc In 1,4-dioxane at 90℃; for 20h; Inert atmosphere; Schlenk technique; Green chemistry;

80%	With copper(II)-citrate; hexamethylenetetramine; hypophosphorous acid In water; N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;
99 %Chromat.	With formic acid; gold nanoparticles on rutile titania; triethylamine In acetone at 60℃; for 0.5h;
	With hydrogen In acetonitrile at 30℃; for 1.5h;
51 %Chromat.	With hydrogen; diisobutylaluminium hydride In tetrahydrofuran at 30℃; for 10h;
	With water; potassium hydroxide In 1,4-dioxane; ethanol at 20℃; Electrochemical reaction;
	With hydrogen In ethanol at 20℃;	1.1.2.1 1.2.1 Provision of a precursor monomer In a 3-neck round bottom flask p-(ethynylphenyl)ethanone (10.0 g, 69.4 mmol) was suspended in EtOH (350 ml_) and Lindlar’s catalyst (300 mg, 3 w%) was added. Air was replaced by hh and the suspension was stirred at RT for 2-16 hours. To monitor the conversion (and thus preventing over-reduction of VPE into the alkane), samples were frequently taken from the reaction mixture and, after evaporation of EtOH under reduced pressure, the conversion was determined by1H-NMR (CDCI3). Afterthe conversion was >90%, the H2-filled balloon was removed and the reaction mixture was concentrated under reduced pressure. The crude product was re-dissolved in CH2CI2 and purified by filtration over Hyflo. The filtrate was concentrated under reduced pressure, giving crude pVPE (p-(vinylphenyl)ethanone) as a yellow liquid in a 99% yield (10.1 g, 69.0 mmol). Melting point 29 °C, melt enthalpy 90.6 J/g.1H-NMR (CDCI3, 600 MHz) d 7.92 (d, J = 8.3 Hz, 2H), 7.48 (d, J =8.2 Hz, 2H), 6.75 (dd, J = 17.6 Hz, 10.9 Hz, 1H), 5.87 (d, J = 17.6 Hz, 1 H), 5.39 (d, J = 10.9 Hz, 1 H), 2.59 (s, 3H).
	With hydrogen In ethanol at 20℃;	2.2.3 2.3 Synthesis of p-(VinylphenvDethenone (VPE) In a 3-neck round bottom flask p-(ethynylphenyl)ethenone (10.0 g, 69.4 mmol) was suspended in EtOH (350 mL) and Lindlar’s catalyst (300 mg, 3 w%) was added. Air was replaced by H2 and the suspension was stirred at RT for 2-16 hours. To monitor the conversion (and thus preventing over-reduction of VPE o into the alkane), samples were frequently taken from the reaction mixture and, after evaporation of EtOH under reduced pressure, the conversion was determined by 1H-NMR (CDCI3). After the conversion was >90%, the H2-filled balloon was removed and the reaction mixture was concentrated under reduced pressure. The crude product was re-dissolved in CH2CI2 and purified by filtration over Hyflo. The filtrate was concentrated under reduced pressure, giving crude VPE as a yellow liquid in a 99% yield (10.1 g, 69.0 mmol). Melting point 29 °C, melt enthalpy 90.6 J/g. 1H- NMR (CDCI3, 600 MHz) d 7.92 (d, J = 8.3 Hz, 2H), 7.48 (d, J = 8.2 Hz, 2H), 6.75 (dd, J = 17.6 Hz, 10.9 Hz, 1 H), 5.87 (d, J = 17.6 Hz, 1 H), 5.39 (d, J = 10.9 Hz, 1 H), 2.59 (s, 3H).

Reference： [1]Wienhoefer, Gerrit; Westerhaus, Felix A.; Jagadeesh, Rajenahally V.; Junge, Kathrin; Junge, Henrik; Beller, Matthias [Chemical Communications, 2012, vol. 48, # 40, p. 4827 - 4829]
[2]Current Patent Assignee: YUNNAN MINZU UNIVERSITY - CN111606774, 2020, A Location in patent: Paragraph 0112-0115
[3]Shen, Guoli; Liu, Haojie; Chen, Jingchao; He, Zhenxiu; Zhou, Yongyun; Wang, Lin; Luo, Yang; Su, Zhimin; Fan, Baomin [Organic and Biomolecular Chemistry, 2021, vol. 19, # 16, p. 3601 - 3610]
[4]Cao, Huanyang; Chen, Tieqiao; Zhou, Yongbo; Han, Daoqing; Yin, Shuang-Feng; Han, Li-Biao [Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 765 - 769]
[5]Li, Shu-Shuang; Tao, Lei; Wang, Fu-Ze-Rong; Liu, Yong-Mei; Cao, Yong [Advanced Synthesis and Catalysis, 2016, vol. 358, # 9, p. 1410 - 1416]
[6]Liu, Jian; Zhu, Yanan; Liu, Chang; Wang, Xiaoshi; Cao, Changyan; Song, Weiguo [ChemCatChem, 2017, vol. 9, # 21, p. 4053 - 4057]
[7]Schmolke, Laura; Gregori, Bernhard J.; Giesen, Beatriz; Schmitz, Alexa; Barthel, Juri; Staiger, Lena; Fischer, Roland A.; Jacobi Von Wangelin, Axel; Janiak, Christoph [New Journal of Chemistry, 2019, vol. 43, # 42, p. 16583 - 16594]
[8]Liu, Cuibo; Lu, Siyu; Wang, Changhong; Wu, Yongmeng; Zhang, Bin [Angewandte Chemie - International Edition, 2020, vol. 59, # 47, p. 21170 - 21175][Angew. Chem., 2020, vol. 132, # 47, p. 21356 - 21361,6]
[9]Current Patent Assignee: UNIVERSITY MEDICAL CENTER UTRECHT; NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH; UTRECHT UNIVERSITY; UNIVERSITY OF TWENTE - WO2021/99578, 2021, A1 Location in patent: Page/Page column 34
[10]Current Patent Assignee: UTRECHT UNIVERSITY; UNIVERSITY MEDICAL CENTER UTRECHT; NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - WO2021/99577, 2021, A1 Location in patent: Page/Page column 34-35

26
[ 42472-69-5 ]
[ 98-80-6 ]
[ 1942-31-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With (E)-N-(pyren-1-ylmethylene)benzenamine; oxygen; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; for 3h;
85%	With anthracen-9-ylmethylene-(4-methoxyphenyl)amine; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; for 2.5h;	Typical procedure fortheoxidative coupling reaction General procedure: A mixture of arylboronic acid (1.0mmol), phenylacety-lene (1.2mmol), Pd(OAc) 2 (1.0mol%), L (1.0mol%) and 1,8-diazabicycloundec-7-ene (DBU) (2.0mmol) in DMF (5mL) was stirred at 100°C in air for 4h. The reaction mixture was then diluted with EtOAc (20mL) and washed with water (3 × 10mL). The organic layer was dried over anhydrous Na 2 SO 4 , filtered and the solvent was removed. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixture to afford the desired product. The products were characterized by 1 H and 13 C NMR analysis.
58%	With iron(III) chloride hexahydrate; silver carbonate In dimethyl sulfoxide at 130℃; for 24h;

Reference： [1]Lakshmipraba, Jagadeesan; Prabhu, Rupesh Narayana; Dhayabaran, Victor Violet [Chemical Papers, 2020, vol. 74, # 10, p. 3661 - 3669]
[2]Lakshmipraba, Jagadeesan; Prabhu, Rupesh Narayana; Dhayabaran, Victor Violet [Transition Metal Chemistry, 2020, vol. 45, # 5, p. 325 - 331]
[3]Location in patent: experimental part You, Xiu L.; Xu, Lai; Hu, Tao [Letters in Organic Chemistry, 2012, vol. 9, # 4, p. 300 - 304]

27
[ 2101-86-2 ]
[ 42472-69-5 ]
1-(4-(1-p-tolyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(ll) sulfate pentahydrate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In methanol; water at 20℃; for 10h; regioselective reaction;	1-(4-(1-p-tolyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone (Compound 13) General procedure: General Procedure for Cycloaddition of Alkyne-Azide: A solution of CuSO45H2O (10 mL, 2 mg, 1 mol % based on azide, with 2.00 g of CuSO45H2O in 10 mL H2O) was added to a mixture of azide (0.79 mmol) and alkyne(0.83 mmol), followed by a solution of dihydropyridine Hantzsch ester (10 mL, 2.2 mg, 1 mol % based on azide, with 2.20 g of dihydropyridine in 10 mL CH3OH) and finally methanol (1 mL) via syringes. The mixture was stirred for a period as indicated at roomtemperature. After being checked by thin-layer chromatography (TLC) (CHCl3/CH3OH), the reaction mixture was concentrated to dryness under reduced pressure. A small amount of water was used to wash the solid product followed by petroleumether (1H NMR spectrumshowed it is pure). If needed, the reaction mixture was loaded onto a short plug of silica gel using a fine solvent gradient (CHCl3/CH3OH) to affordthe analytically pure product. For some substrates, the scales were reduced.

Reference： [1]Jin, Zuxi; Xue, Peng; Fu, Enqin [Synthetic Communications, 2014, vol. 44, # 1, p. 68 - 75]

28
[ 7332-00-5 ]
[ 42472-69-5 ]
1-(4-(1-butyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(ll) sulfate pentahydrate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In methanol; water at 20℃; for 10h; regioselective reaction;	1-(4-(1-butyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone (Compound 17) General procedure: General Procedure for Cycloaddition of Alkyne-Azide: A solution of CuSO45H2O (10 mL, 2 mg, 1 mol % based on azide, with 2.00 g of CuSO45H2O in 10 mL H2O) was added to a mixture of azide (0.79 mmol) and alkyne(0.83 mmol), followed by a solution of dihydropyridine Hantzsch ester (10 mL, 2.2 mg, 1 mol % based on azide, with 2.20 g of dihydropyridine in 10 mL CH3OH) and finally methanol (1 mL) via syringes. The mixture was stirred for a period as indicated at roomtemperature. After being checked by thin-layer chromatography (TLC) (CHCl3/CH3OH), the reaction mixture was concentrated to dryness under reduced pressure. A small amount of water was used to wash the solid product followed by petroleumether (1H NMR spectrumshowed it is pure). If needed, the reaction mixture was loaded onto a short plug of silica gel using a fine solvent gradient (CHCl3/CH3OH) to affordthe analytically pure product. For some substrates, the scales were reduced.

Reference： [1]Jin, Zuxi; Xue, Peng; Fu, Enqin [Synthetic Communications, 2014, vol. 44, # 1, p. 68 - 75]

29
[ 42472-69-5 ]
[ 863098-32-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 4-ethynylacetophenone With silver nitrate In acetone for 0.5h; Stage #2: With N-Bromosuccinimide In acetone at 20℃; for 14h;	To a stirring solution of compound 1.10 (12 g, 83.3 mmoi) in acetone (200 mL) was added AgjSSO* (1 .34 g, 7.9 mmoi) and the the reaction was stirred for 30 mm. MBS (17.7 g, 99.96 mmoi ) was then added and the reaction mixture was stirred at 2G*C for 14 hr. Solids were removed by filtration and the filtrate was concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica get/ ethyl acetate in petroleum ether 5%-10% v/v) to give compound 1.11 as a white solid (14 g, 76 %). N R (400 MHz, DM8O-0 δ 7.95 (d, J = B, 2H )., 7.62 J ~ 8, 2H), 2.58 (s, 3 H ).
	With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 3h; Inert atmosphere;

Reference： [1]Current Patent Assignee: ACHAOGEN INC - WO2013/170165, 2013, A1 Location in patent: Page/Page column 90
[2]Pan, Rui; Shi, Cong; Zhang, Dongquan; Tian, Yang; Guo, Songjin; Yao, Hequan; Lin, Aijun [Organic Letters, 2019, vol. 21, # 22, p. 8915 - 8920]

30
[ 13329-40-3 ]
[ 1066-54-2 ]
[ 42472-69-5 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: 4-Iodoacetophenone; trimethylsilylacetylene With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In toluene at 20℃; for 16h; Inert atmosphere; Stage #2: With potassium carbonate In methanol at 20℃; for 2h;	3. Synthesis of 1-(4-ethynylphenyl)ethan-1-one (3p) In a round bottom flask under Ar, Et3N (5.0 mmol, 1.0 eq) and TMS-acetylene (5.5 mmol, 1.1 eq) were added to a mixture of 4-iodoacetophenone (5.0 mmol 1.0 eq), Pd(PPh3)4 (0.15 mmol, 3 mol%), and CuI (0.45 mmol, 9 mol%) in dry toluene (0.4 M). The reaction was stirred overnight at room temperature. The solvent was then evaporated and the crude was dissolved in DCM and washed twice with water. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The crude was directly dissolved in MeOH (0.1 M) and K2CO3 (5.0 mmol, 1.0 eq) was added. After 2 hours the solvent was removed and the residue was directly purified through column chromatography (pentane/Et2O 95:5) to afford 3p as a white solid (2.2 mmol, 44%). 1H NMR (600 MHz, Chloroform-d) δ 7.91 (d, J = 8.4 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 3.25 (s, 1H), 2.60 (s, 3H). 13C NMR (151 MHz, Chloroform-d) δ 197.4, 137.0, 132.5, 128.4, 127.1, 82.9, 80.5, 26.8.
	With potassium carbonate In methanol; acetonitrile at 40℃;	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.

Reference： [1]Bergamaschi, Enrico; Teskey, Christopher J. [Tetrahedron Letters, 2022]
[2]Mandali, Pavan Kumar; Chand, Dillip Kumar [Catalysis Communications, 2014, vol. 47, p. 40 - 44]

31
[ 935-14-8 ]
[ 42472-69-5 ]

Yield	Reaction Conditions	Operation in experiment
69%	With 5,10,15-tris(pentafluorophenyl)corrole cobalt(III) triphenyl phosphine; sulfuric acid; water In methanol at 80℃; for 84h;	General procedure: A mixture of alkyne 1a (0.5 mmol), F15CCo-PPh3 (0.3 mol%) in CH3OH (0.5 mL), H2SO4 (2 mol%) in CH3OH (0.5 mL) and H2O (4.4 eq.) was heated at 80 °C under air for 12 h in a closed J. Young tube. The progress of the reaction was checked using TLC and GC. After the tube was cooled to R.T., the volatiles were removed under reduced pressure and the pure product 2a as a colorless oil (58 mg, 95% yield) was obtained by flash chromatography of silica gel. acetophenone (2a) Colorless oil (58 mg, 95% yield). 1H NMR (500 MHz, CDCl3) δ 7.96 (d, J = 7.7 Hz, 2H), 7.56 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.7 Hz, 2H), 2.60 (s, 3H). The spectral data were in agreement with literature values.
67%	With iron(III) sulfate hydrate; acetic acid at 95℃; for 24h; Schlenk technique;	Hydration of aromatic terminal alkynes catalyzed by Fe2(SO4)3·nH2O General procedure: Ferric sulfate hydrate (I, 8 mol%), glacial acetic acid (5 mL) and the alkyne (1 - 2 mmol) were introducedinto a 50 mL Schlenk tube, equipped with an air condenser, and the mixture kept under stirring at 95 °C or120 °C, until consumption of the substrate or no further conversion, as evidenced by TLC or GC. Uponcooling, the supernatant solution was poored into water and the residue washed twice with diethyl ether.After extraction with diethyl ether ( 2), the combined organic layers were washed with a saturated aqueoussolution of sodium bicarbonate and then water until neutrality. Alternatively, the crude from the reactions ofsubstrates featuring hydroxyl or carbonyl groups, as for 12, 15, 20 and 22, was obtained by removing aceticacid under vacuum, in order to reduce loss of material during biphasic extraction. The products were purified

Reference： [1]Lai, Jia-Wei; Liu, Zhao-Yang; Chen, Xiao-Yan; Zhang, Hao; Liu, Hai-Yang [Tetrahedron Letters, 2020, vol. 61, # 43]
[2]Bassetti, Mauro; Ciceri, Samuele; Lancia, Federico; Pasquini, Chiara [Tetrahedron Letters, 2014, vol. 55, # 9, p. 1608 - 1612]

32
[ 42472-69-5 ]
[ 90933-84-9 ]
[ 278603-80-8 ]
[ 1600513-96-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With Wender's catalyst In 1,2-dichloro-ethane at 20℃; for 21h;	General alkyne dienophile method General procedure: To an oven-dried or flame-dried vial was added 1.1 equiv. TMSBO 2 as a neat liquid followed by 1,2-dichloroethane (DCE, 0.162 M with respect to VCP). To this solution was added 1 equiv. VCP 1 as a neat liquid, and then 2-5 mol% [(naph)Rh(COD)]SbF6 in one portion. The reaction was stirredfor 6 h or until consumption of 1 could be observed by TLC. The second alkyne was then added and the reaction monitored by TLC for consumption of the intermediate diene. The reaction was quenched with dilute acid and the resulting products purified via column chromatography. Results for these substrates are summarized in Table 1.

Reference： [1]Wender, Paul A.; Fournogerakis, Dennis N.; Jeffreys, Matthew S.; Quiroz, Ryan V.; Inagaki, Fuyuhiko; Pfaffenbach, Magnus [Nature Chemistry, 2014, vol. 6, # 5, p. 448 - 452]

33
[ 1616999-94-0 ]
[ 42472-69-5 ]
[ 1617000-14-2 ]

Yield	Reaction Conditions	Operation in experiment
56.5%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 50℃; for 12h;	6.1.2 2-(2,4-Difluorophenyl)-1-(4-(4-ethyl-1H-1,2,3-triazol-1-yl)piperidin-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (8a) General procedure: To a solution of compound 7 (40mg, 0.11mmol) and but-1-yne (8mg, 1.3equiv) in tert-butyl alcohol (1mL) was added a mixture of CuSO4.5H2O (20mol %) and sodium ascorbate (40mol %) in H2O (0.5mL). The reaction mixture was stirred at 50°C overnight. Then, water (10mL) was added and was extracted with EtOAc (2×20mL). The combined organic layers were washed with water (10mL), dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by flash chromatography using EtOAc/ heptane as eluents (1:5) to give the target compound as a white solid: 20mg, yield 43.3%,

Reference： [1]Jiang, Zhigan; Gu, Julin; Wang, Chen; Wang, Shengzheng; Liu, Na; Jiang, Yan; Dong, Guoqiang; Wang, Yan; Liu, Yang; Yao, Jianzhong; Miao, Zhenyuan; Zhang, Wannian; Sheng, Chunquan [European Journal of Medicinal Chemistry, 2014, vol. 82, p. 490 - 497]

34
[ 42472-69-5 ]
[ 200629-06-7 ]
[ 1616102-60-3 ]

Yield	Reaction Conditions	Operation in experiment
34%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	8.3 Synthesis of the desired substance In a nitrogen atmosphere, 3-allyl-4-bromopyridine (200 mg, 1 mmol), 1-(4-ethynylphenyl)ethanone (160 mg, 1.1 mmol), copper(I) iodide (10 mg, 0.05 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol), triethylamine (4 mL),and N,N-dimethylformamide (4 mL) were reacted at 50°C for 24 hours. After the reaction mixture was allowed to cool to room temperature, water was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with water and brine, and anhydrous sodium sulfate was added to dry the layer. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure and the residue was purified by flash chromatography to obtain the desiredsubstance (90 mg; yield, 34%).

Reference： [1]Current Patent Assignee: ISHIHARA SANGYO KAISHA, LTD. - WO2014/98259, 2014, A1 Location in patent: Page/Page column 39

35
[ 42472-69-5 ]
[ 1616562-54-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trimethylsilylazide; lithium hydroxide monohydrate; anhydrous silver carbonate In dimethyl sulfoxide at 80℃; chemoselective reaction;
	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℃;

Reference： [1]Liu, Zhenhua; Liao, Peiqiu; Bi, Xihe [Organic Letters, 2014, vol. 16, # 14, p. 3668 - 3671]
[2]Ning, Yongquan; Sivaguru, Paramasivam; Zanoni, Giuseppe; Anderson, Edward A.; Bi, Xihe [Chem, 2020, vol. 6, # 2, p. 486 - 496]
[3]Zhang, Yifei; Liao, Yangzhen; Liu, Peijun; Ran, Yu; Liu, Xiaozu [Organic and Biomolecular Chemistry, 2022, vol. 20, # 17, p. 3550 - 3557]

36
[ 941-55-9 ]
[ 42472-69-5 ]
1-(p-toluene)sulfonyl-4-(4-acetylphenyl)-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) thiophene-2-carboxylate In toluene for 15h; Inert atmosphere;
	With copper(I) thiophene-2-carboxylate In water; toluene at 20℃;
	With copper(I) thiophene-2-carboxylate In toluene at 0 - 20℃; Inert atmosphere;

With copper(I) thiophene-2-carboxylate In dichloromethane at 20℃; Inert atmosphere; Sealed tube;

4.2. General procedures of the preparation of 2-(tetrahydrofuran-2-yl)-2H-1,2,3-triazole or 2-(tetrahydrothiophene-2-yl)-2H-1,2,3-triazole General procedure: Aryl ethynylene 1 (0.1 mmol, 1 equiv.) and copper(I) thiophene-2-carboxylate (0.01 mmol, 0.1 equiv.) was added in a 4 mL scintillationvial with a stir bar. After the charge of N2, dichloromethane(0.7 mL) and sulfonyl azide 2 (1.2 equiv.) were added into the sealedvial. The reaction mixture was stirred at room temperature overnightuntil judged by TLC. Dry tetrahydrofuran or tetrahydrothiophene3 (0.3 mL) was injected after the solvent was totally evaporated. The vial was tightly capped and stirred at 90 C overnight(or at 110 C for 6 h). After the completion of the reaction, themixture was cooled to room temperature and purified by columnchromatography using Petroleum ether/ethyl acetate mixture aseluent to afford the desired product 4.

Reference： [1]Miura, Tomoya; Nakamuro, Takayuki; Hiraga, Kentaro; Murakami, Masahiro [Chemical Communications, 2014, vol. 50, # 72, p. 10474 - 10477]
[2]Ma, Xueji; Pan, Shanfei; Wang, Hangxiang; Chen, Wanzhi [Organic Letters, 2014, vol. 16, # 17, p. 4554 - 4557]
[3]Duan, Shengguo; Xue, Bing; Meng, Hui; Ye, Zihang; Xu, Ze-Feng; Li, Chuan-Ying [Chinese Journal of Chemistry, 2021, vol. 39, # 5, p. 1145 - 1152]
[4]Guan, Cong; Ji, Jian; Li, Zi; Wei, Qinghua; Wu, Xiang; Liu, Shunying [Tetrahedron, 2022, vol. 108]

37
[ 3485-80-1 ]
[ 42472-69-5 ]
1-[2-(4-acetylphenyl)ethynyl]-9,10-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In toluene at 60℃; for 2.5h; Inert atmosphere;
78%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In toluene at 65℃; Inert atmosphere;	3.1. Preparation of 1-(R-Ethynyl)-9,10-antraquinones (1a-g) General procedure: A mixture of 1-iodo-9,10-anthraquinone (4.5 mmol) and corresponding 1-alkyne(4.5 mmol), CuI (0.027 mmol), PdCl2(PPh3)2 (0.013 mmol), and Et3N (12.7 mmol) in 50 mLof toluene was stirred under an argon atmosphere at 65 C (2-4 h) until iodide wasconsumed (TLC control). The reaction mixture was cooled and filtered through SiO2(25 30 mm) using toluene as the eluent. The solvents were evaporated, and subsequentrecrystallization gave pure compounds 1a-g.

Reference： [1]Vasilevsky, Sergei F.; Baranov, Denis S.; Mamatyuk, Victor I.; Fadeev, Dmitry S.; Gatilov, Yurii V.; Stepanov, Aleksandr A.; Vasilieva, Nadezhda V.; Alabugin, Igor V. [Journal of Organic Chemistry, 2015, vol. 80, # 3, p. 1618 - 1631]
[2]Alabugin, Igor V.; Baev, Dmitry Sergeevich; Krivenko, Ol’Ga Leonidovna; Sorokina, Irina Vasilievna; Tolstikova, Tatyana Genrikhovna; Vasilevsky, Sergey Francevich [Molecules, 2021, vol. 26, # 22]

38
[ 42472-69-5 ]
[ 1009-61-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With Perfluorooctanesulfonic acid; C8AgF17O3S*H2O; In water; at 100℃; for 8h;Darkness;	General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 799-800,p. 122 - 127

39
[ 141-32-2 ]
[ 42472-69-5 ]
3-(4-acetylbenzoyl)-4,5-dihydro-isoxazole-5-carboxylic acid butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tert-butyl isocyanide; copper(II) nitrate trihydrate In benzonitrile at 60℃; Schlenk technique; Inert atmosphere; regioselective reaction;
71%	With copper(II) nitrate In benzonitrile at 60℃;	3 3- (4-acetyl-benzoyl) -4,5-dihydro-isoxazole-5-carboxylic acid butyl ester using the following steps: at 1000Ml of the reaction vessel was charged with 21.7 g of 4-ethynylacetophenone,346.8 grams of n-butyl acrylate,145.0 grams of copper nitrate,25.0 grams2-hexanitrile addedObjects,750 ml of benzonitrile,Heated to 60 ° C.The reaction was followed by thin layer chromatography,To the reaction material disappeared; After the reaction,To the system to add water quenching reaction,The product was extracted with ethyl acetate,The organic phase was washed with saturated brine,After drying, the solvent was removed by rotary evaporator,The crude product;The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5: 1)To give 33.65 g of butyl 3- (4-acetylbenzoyl) -4,5-dihydroisoxazolyl-5-carboxylate,The yield was 71%.

Reference： [1]Gao, Mingchun; Li, Yingying; Gan, Yuansheng; Xu, Bin [Angewandte Chemie - International Edition, 2015, vol. 54, # 30, p. 8795 - 8799][Angew. Chem., 2015, vol. 127, # 30, p. 8919 - 8923,4]
[2]Current Patent Assignee: SHANGHAI UNIVERSITY - CN104910090, 2017, B Location in patent: Paragraph 0043-0044

40
7-bromo-5-methyl-2-phenyl-1H-indole [ No CAS ]
[ 42472-69-5 ]
1-(4-((5-methyl-2-phenyl-1H-indol-7-yl)ethynyl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 20 - 80℃; for 0.5h; Inert atmosphere;	4.2.2. Typical procedure for the preparation of 2,5-disubstituted-7-alkynylindoles (6). General procedure: Synthesis of 5-methyl-2-phenyl-7-(phenyl-ethynyl)-1H-indole (6a). In a 50 mL Carousel Tube Reactor (RadelyDiscovery Technology) containing a magnetic stirring bar HP(t-Bu)3BF4 (5.8 mg, 0.02 mmol) and Pd2(dba)3 (9.2 mg, 0.01 mmol)were dissolved at room temperature with 1.0 mL of 1,4-dioxaneunder nitrogen. Then, 7-bromo-5-methyl-2-phenyl-1H-indole 5a(146.0 mg, 0.5 mmol), phenylacetylene (65.8 m l, 0.6 mmol), Cs2CO3(325.8 mg, 1 mmol), and 1.0 mL of solvent were added. The reaction mixture was stirred for 0.5 h at 80°C. After this time, the reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with a saturated NaCl solution. The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure. The residue was puried by chromatography (silica gel, n-hexane/EtOAc 99/1) to afford 147.4 mg (96% yield) of 5-methyl-2-phenyl-7-(phenylethynyl)-1H-indole 6a as a brown solid. Mp:123 e 125C; IR (KBr): 3427, 3123, 2905, 2334, 2374, 1605, 1454,1071 (cm1);1H NMR (CDCl3): d 8.55 (br s, 1H), 7.73 e 7.67 (m, 4H),7.50 e 7.43 (m, 6H), 7.37 (t, J7.2 Hz, 1H), 7.30 (s, 1H), 6.81 (d,J2.0 Hz, 1H), 2.56 (s, 3H);13C NMR (CDCl3): d 138.3, 135.9, 132.2,131.7, 129.6, 129.2, 129.1, 128.5,128.4,127.9,127.1, 125.3,123.4,121.5,105.6, 100.1, 93.2, 85.8, 21.4; MS m/z (%): 307 (M, 100); 244 (80).Anal. Calcd for C23H17N, C, 89.87; H, 5.57; N, 4.56; found C, 89.95; H,5.58; N, 4.57.

Reference： [1]Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella; Iazzetti, Antonia; Verdiglione, Rosanna [Tetrahedron, 2015, vol. 71, # 49, p. 9346 - 9356]

41
[ 42472-69-5 ]
[ 100-52-7 ]
[ 34838-64-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With phosphonic Acid In hexane; water at 110℃; for 36h; Schlenk technique; Green chemistry;	Chalcone (3a); Typical Procedure General procedure: PhC≡CH (1a; 0.5 mmol), PhCHO (2a; 0.6 mmol), and 50% aq H3PO4 (0.5 mmol) were added to a 5 mL Schlenk tube, and the mixture was vigorously stirred at 110 °C for 24 h. The mixture was then cooled tor.t. and EtOAc (20 mL) was added. The solution was washed with water (2 × 6 mL) and the organic phase was dried (MgSO4), concentrated, and purified by column chromatography [silica gel, EtOAc-PE (1:20)] to give a pale-yellow solid

Reference： [1]Zhou, Yongbo; Li, Zhongwen; Yang, Xiao; Chen, Xiulin; Li, Mei; Chen, Tieqiao; Yin, Shuang-Feng [Synthesis, 2016, vol. 48, # 2, p. 231 - 237]

42
[ 42472-69-5 ]
[ 4559-70-0 ]
1-(4-acetylphenyl)-2-(diphenylphosphoryl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	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)].
74%	With silver orthophosphate; trimethylsilylazide; water; oxygen In dimethyl sulfoxide at 65℃; Schlenk technique; Inert atmosphere;
68%	With oxygen; rhodamine B In isopropyl alcohol at 20℃; for 12h; Irradiation; regioselective reaction;

53%

With oxygen; copper(l) cyanide In dimethyl sulfoxide at 55℃; for 24h;

General procedure for construction of β-ketophosphine oxides General procedure: An oven-dried flask with the mixture of CuCN (0.025 mmol), alkynes 1 (0.5 mmol), H-phosphine oxides 2 (1.0 mmol) and DMSO (1.0 ml) was charged with O2. The reaction mixture was stirred at 55 °C for 24 hours. After completion of the reaction, water (10 ml) was added and extracted with EtOAc (5.0 ml×3). The combined organic layers were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting mixture purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 3

Reference： [1]Zhong, Wenwu; Tan, Tao; Shi, Lei; Zeng, Xue [Synlett, 2018, vol. 29, # 10, p. 1379 - 1384]
[2]Liu, Binbin; Song, Qingmin; Liu, Zhaohong; Wang, Zikun [Advanced Synthesis and Catalysis, 2021, vol. 363, # 13, p. 3214 - 3219]
[3]Bu, Mei-Jie; Lu, Guo-Ping; Cai, Chun [Catalysis science and technology, 2016, vol. 6, # 2, p. 413 - 416]
[4]Zhong, Wen-Wu; Zhang, Qiang; Li, Meng-Shun; Hu, Dong-Yan; Cheng, Ming; Du, Feng-Tian; Ji, Jian-Xin; Wei, Wei [Synthetic Communications, 2016, vol. 46, # 16, p. 1377 - 1385]

43
[ 42472-69-5 ]
2,2-dibromo-1-(4-acetylphenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-Bromosuccinimide; perchloric acid In water; acetonitrile at 20℃; for 3h; Inert atmosphere;	General procedure for the preparationof α,α-dibromoketones 5 General procedure: Acetonitrile (2 cm3/mmol), water (1 cm3/mmol), and HClO4 (10 mol %) was added to a mixture of alkyne 4(1.0 mmol) and NBS (2.5 mmol). The resultant mixture was stirred for the time indicated in Table 1. Then, thereaction mixture was diluted with Et2O (8 cm3/mmol) andwashed with a saturated solution of Na2CO3 (3 cm3/mmol),Na2S2O3 (3 cm3/mmol), water (3 cm3/mmol), and brine (3 cm3/mmol). The organic layer was dried over MgSO4,concentrated under reduced pressure and column chromatographyon silica gel afforded the a,a-dibromoketones 5.
77%	With N-Bromosuccinimide; eosin In water at 20℃; for 4h; Inert atmosphere; Irradiation;
75%	With toluene-4-sulfonic acid; lithium bromide In methanol; water at 20℃; for 4.5h; Inert atmosphere; Electrochemical reaction;

Reference： [1]Kotek, Vladislav; Polk, Peter; Tobrman, Tom [Monatshefte fur Chemie, 2016, vol. 147, # 2, p. 405 - 412]
[2]Finck, Lucie; Brals, Jeremy; Pavuluri, Bhavana; Gallou, Fabrice; Handa, Sachin [Journal of Organic Chemistry, 2018, vol. 83, # 14, p. 7366 - 7372]
[3]Wang, Dan; Wan, Zhaohua; Zhang, Heng; Lei, Aiwen [Advanced Synthesis and Catalysis, 2021, vol. 363, # 4, p. 1022 - 1027]

44
[ 42472-69-5 ]
[ 10537-63-0 ]
[ 937-30-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 94% 2: 5 %Chromat.	With hydrogen In toluene at 110℃; for 4h; Schlenk technique; chemoselective reaction;	Semi-Hydrogenation of Alkynes 1a-l; General Procedure General procedure: The starting alkyne 1 (0.5 mmol) and dodecane as internal standard(0.22 mmol, 50 μL) were added to a suspension of the Cu-Pd-NPs/MCM-48 catalyst (10 mg) in toluene (5 mL). All reactions werecarried out in a Schlenk-type flask, fitted with a reflux condenser andsealed with a rubber septum. The reaction flask was purged and filledwith H2 (1 atm) through a balloon connected to the flask by a needle,and then heated at 110 °C. Then, the reaction mixture was centrifugedand the supernatant removed. The solvent was evaporated invacuo, and the crude product was purified by flash column chromatography(silica gel, hexane/EtOAc). The recovered solid catalyst waswashed with toluene (3 × 2 mL), dried in an oven, calcined at 150 °C(4 h), and reduced in H2 atmosphere at 200 °C before its reuse. The following known compounds included in Table 2 were characterizedby comparison of their chromatographic and spectroscopic data (FTIR,1H NMR, 13C NMR, and MS) with those described in the literature.Styrene (2a)18Yield: 46 mg (0.44 mmol, 89%); colorless liquid.IR (film): 3082, 3060, 3027, 1630, 1496, 1449, 992, 909, 777, 698 cm-1.1H NMR (300 MHz, CDCl3): δ = 7.35 (m, 2 H), 7.25 (m, 3 H), 6.7 (dd, J =10.8, 17.1 Hz, 1 H), 5.71 (d, J = 17.1 Hz, 1 H), 5.20 (d, J = 10.8 Hz, 1 H).13C NMR (75 MHz, CDCl3): δ = 137.5, 128.5, 127.7, 126.1, 136.9, 113.7.MS: m/z (%) = 104 (100, [M+]), 103 (40), 78 (35), 77 (17), 51 (17).
	With hydrogen; 1,3,5-trimethyl-benzene In acetonitrile at 30℃; for 1.5h;

Reference： [1]Buxaderas, Eduardo; Volpe, María Alicia; Radivoy, Gabriel [Synthesis, 2019, vol. 51, # 6, p. 1466 - 1472]
[2]Yang, Shuliang; Cao, Changyan; Peng, Li; Zhang, Jianling; Han, Buxing; Song, Weiguo [Chemical Communications, 2016, vol. 52, # 18, p. 3627 - 3630]

45
[ 42472-69-5 ]
[ 4559-70-0 ]
1,2-bis(diphenylphosphinyl)-2-(4-acetophenyl)ethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With air In N,N-dimethyl-formamide at 150℃; for 22h;
48%	Stage #1: Diphenylphosphine oxide With lithium tert-butoxide In tetrahydrofuran for 1h; Schlenk technique; Inert atmosphere; Stage #2: 4-ethynylacetophenone In tetrahydrofuran at 70℃; for 4h; Schlenk technique; Inert atmosphere;	2 Experimental procedures for the base-catalyzed double addition of phosphine oxidesto alkyn General procedure: In a Schlenk flask wereplaced diphenylphosphine oxide (0.2 mmol), and tBuOLi of THF solution (5 mol%, 0.01 mmol) in THF (0.15mL) under nitrogen. The mixture was stirred at ambient temperature for 1 h. Etynylbenzene(0.1 mmol) was added to the solution under nitrogen and the mixture was heatedat 70 °C for 4 h.

Reference： [1]Guo, Haiqing; Yoshimura, Aya; Chen, Tieqiao; Saga, Yuta; Han, Li-Biao [Green Chemistry, 2017, vol. 19, # 6, p. 1502 - 1506]
[2]Yoshimura, Aya; Saga, Yuta; Sato, Yuki; Ogawa, Akiya; Chen, Tieqiao; Han, Li-Biao [Tetrahedron Letters, 2016, vol. 57, # 30, p. 3382 - 3384]

46
[ 42472-69-5 ]
[ 85331-33-5 ]
5-((4-acetylphenyl)ethynyl)-3-chloropicolinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20℃;	To a solution of 1-(4-ethynylphenyl)ethanone (commercially available) (1 eq) <strong>[85331-33-5]3,5-dichloropicolinonitrile</strong> (1 eq), dichlorobis(triphenylphosphine)-palladium (II) (20 mol %), copper iodide (10 mol %) and DMF:Triethylamine (10:1) (0.13 M) was stirred at ambient temperature overnight. The reaction mixture was then diluted with ethyl acetate and sodium bicarbonate solution. The two phases were separated, and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-100% ethyl acetate in hexane and 5-((4-acetylphenyl)ethynyl)-3-chloropicolinonitrile was isolated as a yellow solid

Reference： [1]Patent: US9408907,2016,B2 .Location in patent: Page/Page column 165

47
[ 42472-69-5 ]
[ 623-47-2 ]
3-(4-acetylbenzoyl)isoxazole-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With copper(II) nitrate trihydrate In benzonitrile at 50℃;	3 Example 3: 3-(4-acetylbenzoyl)isoxazolyl-5-carboxylic acid ethyl ester 3-(4-acetylbenzoyl)isoxazolyl-5-carboxylic acid ethyl ester using the following steps : (1) in 1000 ml according to the reaction vial 1 : 4.0: 8.0 to the molar ratio of 14.7 g propiolic acid ethyl ester, 86.7 g 4-ethynyl hypnone, 290.0 g copper nitrate, then adding 750 ml of benzonitrile, heating to 50 °C. Method for thin-layer chromatography for tracking of the reaction, to the reaction raw materials dematerialised ; (2) after the reaction, the reaction is quenched with water to the system, the extraction of the product with ethyl acetate, saturated salt water for washing, drying by rotary evaporimeter remove the solvent, get the crude product ; (3) of the crude product by column chromatography (petroleum ether: ethyl acetate = 30:1) purified, get 33.65 g 3-(4-acetylbenzoyl)isoxazolyl-5-carboxylic acid ethyl ester the yield is 77%.

Reference： [1]Current Patent Assignee: SHANGHAI UNIVERSITY - CN105237491, 2016, A Location in patent: Paragraph 0017; 0018

48
[ 941-55-9 ]
[ 42472-69-5 ]
[ 108-18-9 ]
N1,N1-diisopropyl-N2-(4-methylbenzenesulfonyl)-2-(4-acetylphenyl)acetamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With Cu(at)C, generated by pyrolysis of Cu₃(1,3,5-benzenetricarboxylate)₂ In acetonitrile at 25℃; for 3h; Inert atmosphere;	4. General procedure for the Cu(at)C-catalyzed N-sulfonyl amidine synthesis General procedure: A 15 mm flame-dried test tube, which was equipped with a magnetic stir bar and charged with Cu(at)C (5 mol %, 0.025 mmol), was evacuated and back filled with N2. After 0.5 mL of CH3CN was added, terminal alkyne (0.5 mmol), amine (0.6 mmol), sulfonyl azide (0.6 mmol), and CH3CN (0.5 mL) were added in sequence. Triethylamine (0.6 mmol) was added prior to the addition of amine, if necessary. The solution was stirred for 3 h at room temperature under N2 balloon. The reaction was diluted by adding EtOAc or DMF (if case of 4b, 4d, 4g, and 6d) and filtered through silica plugs. The silica were washed with EtOAc several times and the solvent was removed under vacuo. The crude residue was purified by column chromatography with EtOAc:hexane to give the N-sulfonyl amidine product.

Reference： [1]Kim, Myeong Jin; Kim, Bo Ram; Lee, Chang Yeon; Kim, Jinho [Tetrahedron Letters, 2016, vol. 57, # 36, p. 4070 - 4073]

49
[ 14235-81-5 ]
[ 42472-69-5 ]
1-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)phenyl)ethanone [ No CAS ]
[ 30405-78-8 ]
[ 217451-41-7 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12348 - 12351

50
[ 42472-69-5 ]
(E)-1,4-bis(4-acetylphenyl)but-3-en-1-yne [ No CAS ]
(Z)-1,4-bis(4-acetylphenyl)but-3-en-1-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 82% 2: 6%	With [(Me₃P)₃Ru(-OH)₃Ru(PMe₃)₃]⁺[OPh]^-*(HOPh)_0.2 at 100℃; for 2h; Inert atmosphere; Schlenk technique;	4-Acetylphenylacetylene (2e) 2e (144.3 mg, 1.00 mmol) was treated by 1·(HOPh)0.2(4.3 mg, 0.0052 mmol) at 100C for 2 h to give(E)-1,4-bis(4-acetylphenyl)but-3-en-1-yne (E-3e) and (Z)-1,4-bis(4-acetylphenyl)but-3-en-1-yne (Z-3e) in 82% and 6% yields,respectively. These products were characterized by GC and NMR.E-3e:1H NMR (CDCl3): 2.61 (s, 6H, Me), 6.51 (d, J = 16 Hz, 1H,=CH), 7.11 (d, J = 16 Hz, 1H, =CH), 7.51 (d, J = 8 Hz, 2H, C6H4), 7.56(d, J = 8 Hz, 2H, C6H4), 7.93-7.96 (m, 4H, C6H4). Z-3e:1H NMR(CDCl3): 6.10 (d, J = 12 Hz, 1H, =CH), 6.80 (d, J = 12 Hz, 1H, =CH),the aromatic protons were obscured because of overlapping withE-3e.

Reference： [1]Kiyota, Sayori; Soeta, Hirofumi; Komine, Nobuyuki; Komiya, Sanshiro; Hirano, Masafumi [Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 419 - 428]

51
[ 12093-10-6 ]
[ 42472-69-5 ]
C₂₁H₁₆FeO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 4-ethynylacetophenone With potassium hydroxide In methanol; water for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: ferrocenecarboxaldehyde In methanol; water at 20℃; Inert atmosphere; Schlenk technique;	5.2.1. Synthesis of (h5-C5H5)-Fe-(h5-C5H4)-(E)-CH2]CH2-CO-C6H4-p-C≡C-H (2) Potassium hydroxide (2.0 g, 36 mmol) dissolved in methanol/H2O (30/10 mL) were mixed, portion wise, with 4-ethynylacetophenone, C, (300 mg; 2.1 mmol) and allowed toreact for 20 min. Later, ferrocenecarboxaldehyde (450 mg,2.1 mmol) was added, and allowed to react to room temperatureuntil the precipitation of red-purple color. The solid formed, containingto desired compound, was separated by fritted funnelfiltration. Yield 56% (395 mg).

Reference： [1]Escobar, Carlos A.; Gutierrez, Daniela; Verdugo, Miguel; Madrid, Franco; Santos, Juan C.; Jara-Ulloa, Paola; Trujillo, Alexander [Journal of Organometallic Chemistry, 2017, vol. 830, p. 1 - 10]

52
[ 42472-69-5 ]
[ 824-79-3 ]
(E)-1-((2-chloro-2-(4-ethynylphenyl)ethenyl)sulfonyl)-4-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol at 90℃; for 3h; Inert atmosphere;	8 Synthesis Example 8 Synthesis of (E) -1 - ((2-chloro-2- (4-ethanophenyl) ethenyl) sulfonyl) -4-methylbenzene 0.20 mmol was added to the reactorAcetylene acetylene acetylene, 0.30 mmolP-methylphenylsulfinic acidsodium,0.40 mmol of ferric chloride hexahydrate, 2.0 mL of trifluoroethanol solvent. Heated to 90 ° C under a nitrogen atmosphere,After stirring for 3 h, the reaction was stopped, cooled to room temperature, extracted with methylene chloride, dried, and the solvent was removed by distillation under reduced pressure. The crude product was separated by column chromatography to give the desired product in 80% yield.

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN106083669, 2016, A Location in patent: Paragraph 0051; 0052; 0053

53
N-(5-iodoquinolin-8-yl)acetamide [ No CAS ]
[ 42472-69-5 ]
5-(4-acetophenylethynyl)-8-(acetyl)aminoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With bis-triphenylphosphine-palladium(II) chloride; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20 - 50℃; for 12h; Inert atmosphere;	26 Preparation Example 26 In 10mLThe reaction tube was added0.2 mmol of 8- (acetyl) aminoquinoline, 0.22 mmol of I2 and 1 mL of DMF under nitrogen atmosphere at 50 & lt; 0 & gt; C for 18 h. After completion of the reaction, the reaction was allowed to cool to room temperature and then added under a nitrogen atmosphere0.3 mmol of 4-acetylphenylacetylene, 2 mmol of potassium tert-butoxide, 0.002 mmol of bis (triphenylphosphine) phosphine dichloride, 1 mL of DMF,50 ° C for 12 hours. After the reaction, the reaction mixture was filtered, concentrated and separated by column chromatography5- (4-acetophenylethynyl) -8- (acetyl) aminoquinoline in 71% yield.

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN106905233, 2017, A Location in patent: Paragraph 0071; 0072

54
[ 42472-69-5 ]
[ 66003-78-9 ]
[ 1942-31-0 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5454 - 5457

55
[ 941-55-9 ]
[ 42472-69-5 ]
[ 7654-06-0 ]
4-(4-acetylphenyl)-N-(1-phenylvinyl)-1-tosyl-1H-1, 2, 3-triazol-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 4-toluenesulfonyl azide; 4-ethynylacetophenone With copper(l) iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Schlenk technique; Sealed tube; Inert atmosphere; Stage #2: 3-phenyl-2H-azirine In dichloromethane at 0 - 20℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere;	14 Example 14 In a 25 mL dry Schlenk reaction tube equipped with a magnetic stirrer, 0.010g (0.05 mmoL) of cuprousiodideand 0.094 g (0.65 mmoL) of para-acetylphenylacetylene were charged and sealed with a rubber stopper.The reaction tube pump vacuum, nitrogen,repeated 3 times.Separately, 1 mL of methylene chloride, 105 μL (0.6 mmol) of diisopropylethylamine, and 135 μL (0.6 mmol) of p-toluenesulfonyl azide in methylene chloride (70% strength) .The reaction tube was placed in an ice-water bathand stirred for half an hour. Then, 70 μL (0.5 mmoL) of 3-phenyl-2H-azirine was injected dropwise and the reaction was continued in an ice bath(ice bath slowly dissolving andwarmingto room temperature).After 12 hours of reaction in an ice-water bath and room temperature, the reaction mixture was directly passed through a silica gel column(volume ratio of ethyl acetate to petroleum ether being 1: 4) to give 0.098 g of a pale yellow solid product with a yield of 43%
43%	Stage #1: 4-toluenesulfonyl azide; 4-ethynylacetophenone With copper(l) iodide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere; Schlenk technique; Cooling with ice; Stage #2: 3-phenyl-2H-azirine In dichloromethane at 0 - 20℃; for 11.5h; Inert atmosphere; Schlenk technique;

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN105130915, 2017, B Location in patent: Paragraph 0101-0105
[2]Zhou, Wei; Zhang, Min; Li, Hanhui; Chen, Wanzhi [Organic Letters, 2017, vol. 19, # 1, p. 10 - 13]

56
1-methyl-4-[(trifluoromethyl)selanyl]sulfonyl}benzene [ No CAS ]
[ 42472-69-5 ]
1-{4-[(E)-2-(4-methylphenylsulfonyl)-1-[(trifluoromethyl)selanyl]ethenyl]phenyl}ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In tetrahydrofuran at 25℃; stereoselective reaction;	Typical procedure General procedure: To a flask equipped with a magnetic stirbar were added 1 (0.25 mmol, 1.1 equiv), alkyne 2 (0.23 mmol,1.0 equiv), and anhydrous THF (1 mL). The reaction was stirredat 25 °C for 15-18 hours (conversion was checked by 19F NMRwith PhOCF3 as internal standard). The crude residue was purifiedby chromatography to afford the desired products 3-5.

Reference： [1]Ghiazza, Clément; Tlili, Anis; Billard, Thierry [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2626 - 2630]

57
[ 42472-69-5 ]
[ 135579-93-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With manganese powder; methanesulfonic acid; trifuran-2-yl-phosphane; palladium diacetate; Trimethylacetic acid In tetrahydrofuran at 40℃; for 24h; Inert atmosphere; Green chemistry;	6 Example 6: Synthesis of 2,3-bis(4-acetylphenyl)-1,3-dibutylene In a 25 mL reactor, methane sulfonic acid (0.014 g, 0.15 mmol), pivalic acid (0.087 g, 0.85 mmol), manganese powder (0.027 g, 0.5 mmol),Tris(2-furyl)phosphine (0.009 g, 0.04 mmol), palladium acetate (0.005 g, 0.02 mmol), nitrogen substitution three times,Add 3 mL of dry tetrahydrofuran and add under stirring4-ethynylacetophenone (0.072 g, 0.5 mmol) was stirred at 40° C. for 24 h.Column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether) gave 0.03 g of 2,3-bis(4-acetylphenyl)-1,3-dibutene in a 62% yield. white solid
60%	With palladium (II) 2,4-pentanedionate; toluene-4-sulfonic acid; (tert-butyl)diphenylphosphane; zinc powder; Trimethylacetic acid In tetrahydrofuran at 35℃; for 2h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN107556153, 2018, A Location in patent: Paragraph 0057; 0058; 0059; 0060
[2]Guo, Hongyu; Zhang, Sheng; Li, Yang; Yu, Xiaoqiang; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming [Angewandte Chemie - International Edition, 2022, vol. 61, # 13][Angew. Chem., 2022, vol. 134, # 13]

58
[ 75-22-9 ]
[ 1246242-17-0 ]
[ 42472-69-5 ]
C₁₃H₂₀BNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With (2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl)AuNTf<SUB>2</SUB> In dichloromethane at 20℃; for 3h; regiospecific reaction;

Reference： [1]Yang, Ji-Min; Zhao, Yu-Tao; Li, Zi-Qi; Gu, Xue-Song; Zhu, Shou-Fei; Zhou, Qi-Lin [ACS Catalysis, 2018, vol. 8, # 8, p. 7351 - 7355]

59
[ 42472-69-5 ]
[ 2114-00-3 ]
4-(4-acetylphenyl)-2-methyl-2-(1-oxo-1-phenylpropan-2-yl)naphthalen-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With 1,10-Phenanthroline; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere; diastereoselective reaction;
54%	With 1,10-Phenanthroline; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate In toluene at 120℃; for 16h; Schlenk technique; Sealed tube; Inert atmosphere;	22 Example 22 2-Bromopropiophenone (0.2 mmol) of the formula I-1, p-acetylphenylacetylene (0.1 mmol) of the formula II-4, Cu(MeCN)4PF6 (10 mol%) was added to the Schlenk tube-seal reactor. ),1,10-phen (20 mol%), K2CO3 (2equiv) and toluene (2 mL),The reaction was stirred at 120 ° C under argon.The reaction was completely detected by TLC (about 16 hours).Then will reverseThe solution was filtered through a short silica gel column and the filter cake was washed with ethyl acetate.Concentrated under reduced pressure to give a residue.The residue was separated by silica gel column chromatography to give the desired product of formula III-4.Yield 54%

Reference： [1]Ouyang, Xuan-Hui; Hu, Chao; Song, Ren-Jie; Li, Jin-Heng [Organic Letters, 2018, vol. 20, # 15, p. 4659 - 4662]
[2]Current Patent Assignee: NANCHANG HANGKONG UNIVERSITY - CN108863740, 2018, A Location in patent: Paragraph 0051-0053

60
[ 42472-69-5 ]
[ 2926-29-6 ]
C₁₁H₇F₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With pyridine; bis(trichloromethyl) carbonate In 1,2-dichloro-ethane at 60℃; for 12h; Inert atmosphere; Sealed tube;	6.1; 6.2; 8 Example 6 (1) 1.0 mmol of 4-ethynylacetophenone, 1.5 mmol of sodium trifluoromethanesulfinate, 1.0 mmol of phosgene, and 0.1 mmol of pyridine were added to 3 mL of DCE, sealed with nitrogen, sealed at 60 ° C. The tube reacted for 12 hours.

Reference： [1]Current Patent Assignee: UNIV LISHUI - CN108569942, 2018, A Location in patent: Paragraph 0065; 0067; 0068; 0069

61
[ 128-08-5 ]
[ 42472-69-5 ]
C₁₄H₁₃NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: N-Bromosuccinimide; 4-ethynylacetophenone With water at 80℃; for 1h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 2h;	Representative procedure for the synthesis of α-imino ketones from alkynes General procedure: To a stirred solution of phenylacetylene 1a (102.12 mg, 1.0 mmol) and H2O (1.0 mL) in a vial (4.0 mL) were added N-Bromosuccinimide (356 mg, 2.0 mmol). Upon sealing by a septum cap and stirring at 80 °C for 1 h, the reaction mixture was then cooled to room temperature. Subsequently, acetone (1 mL) and DBU (3.0 mmol) were introduced into the reaction mixture, and the stirring was continued at room temperature for additional 2 h. After completion of reaction as monitored by TLC analysis, acetone was evaporated in vaccuo and crude product was poured into water and then extracted with CH2Cl2 (3×10 mL). The organic phase was washed with water (3×10 mL), dried over Na2SO4, filtered and concentrated in vaccuo.The crude product was purified by a short-pad silica gel column chromatography with petroleum ether as eluent to give compound 2a as a white solid (154.1 mg, 71% yield).

Reference： [1]Wei, Ting; Zeng, Yongming; He, Wei; Geng, Lili; Hong, Liang [Chinese Chemical Letters, 2019, p. 383 - 385]

62
[ 42472-69-5 ]
ethyl 1-[(4-methylphenyl)sulfonyl]-2-aziridineacrylate [ No CAS ]
C₂₄H₂₅NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 4-ethynylacetophenone; ethyl 1-[(4-methylphenyl)sulfonyl]-2-aziridineacrylate With bis(norbornadiene)rhodium(l)tetrafluoroborate In 1,2-dichloro-ethane for 0.5h; Inert atmosphere; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In 1,2-dichloro-ethane at 50℃; for 1h; Inert atmosphere;	General Procedure for Synthesis of Pyrroles 9 General procedure: To a solution of 5 (0.2 mmol, 1 equiv.) and [Rh(NBD)2]BF4 (5 mol%) in 1,2-DCE (1 mL) was added the corresponding acetylene (0.3 mmol, 1.5 equiv.) in 1,2-DCE (1 mL). The resulting mixture was stirred for 0.5 h. Upon the addition of DABCO (0.1 mmol, 0.5 equiv.), the mixture was heated to 50°C for 1 h. The reaction mixture was then quenched with the addition of trifluoroacetic acid (0.3 mmol,1.5 equiv). The solvent was removed under reduced pressure and the residue was purified by columnchromatography using CH2Cl2/hexane as the eluent to give the desired pyrrole 9.

Reference： [1]Wan, Shu-Hao; Liu, Shiuh-Tzung [Tetrahedron, 2019, vol. 75, # 9, p. 1166 - 1170]

63
[ 42472-69-5 ]
(py)CuIII(CF3)3 [ No CAS ]
(Z)-1-(4-(3,3,3-trifluoroprop-1-en-1-yl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylsilane; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; Green chemistry; stereoselective reaction;	3 Example 3 A method of preparing a cis-trifluoromethylstyrene compound using the following process steps:in room temperature, Add NaOtBu 38 mg (0.4 mmol) to a 25 mL Schlenk tube equipped with a stir bar. Then seal the tube with a rubber stopper, Vacuum and refill with dry nitrogen three times . Next, 47 mg (0.4 mmol) of triethylsilane was weighed and dissolved in 2 mL of DMF solution. A mixture of the two was injected into the reaction tube through a syringe. The reaction tube was reacted in an oil bath at 110 ° C for 1 h. Subsequently, Weigh 35 mg (0.1 mmol) of copper trifluoromethyl compound 1 with a balance And 4-acetylphenylacetylene 14 mg (0.1 mmol), And dissolve the two in 1 mL of DMF. Then, the mixture is injected into the reaction tube with a syringe. Continue to react for 12 h. After the reaction is completed, it is cooled to room temperature. The reaction system was diluted with 15 mL of dichloromethane and filtered. The filtrate was washed three times with 60 mL of saturated brine. The organic layer was dried over anhydrous Na 2 SO 4 . Add a small amount of silica gel to spin column chromatography. The product 3c was obtained as a colorless oil (yield 51%).

Reference： [1]Current Patent Assignee: JIANGNAN UNIVERSITY - CN109503338, 2019, A Location in patent: Paragraph 0051-0057

64
[ 128-37-0 ]
[ 42472-69-5 ]
C₂₅H₃₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h; regioselective reaction;	Typical synthetic procedure for compounds 3, 4 (with 3a asan example): General procedure: to a solution of phenylacetylene (1a)(0.055 mL, 0.5 mmol), 2,6-di-tert-butyl-4-methylphenol(BHT) (2a) (133 mg, 0.6 mmol), NaN3 (39 mg, 0.6 mmol)and KF (58 mg, 1.0 mmol) in DMF (1 mL) at 50 °C, Ag2CO3(41 mg, 0.15 mmol) was added. The reaction mixture wasthen stirred for 6 h when TLC conformed that substrate 1a was consumed. The resulting reaction mixture was cooled toroom temperature and extracted by dichloromethane(3×15 mL). The organic layer was washed with brine(3×40 mL), dried over MgSO4 and concentrated. Purificationof the crude product via flash column chromatography (silicagel; petroleum ether) and concentratinon in vacuo affordedthe desired product of 3a-N2/3a-N1 in 91% yield.

Reference： [1]Liu, Zhenhua; Hao, Wenjing; Gao, Wen; Zhu, Guangyu; Li, Xiang; Tong, Lili; Tang, Bo [Science China Chemistry, 2019, vol. 62, # 8, p. 1001 - 1006]

65
[ 75-77-4 ]
[ 42472-69-5 ]
[ 75883-03-3 ]

Yield	Reaction Conditions	Operation in experiment
47%	With diethylzinc In hexane; acetonitrile at 80℃; for 20h; Schlenk technique; Inert atmosphere;	General Procedures for the Et2Zn-mediated silylation of terminal alkynes: To a 25 mL Schlenk flask alkyne (2 mmol), chlorosilane (2 mmol), solvent (10 mL) and 1 M n-hexane solution of Et2Zn (1 mL) is added and the mixture is stirred at 80 °C for 20 h unless otherwise stated. After cooling, the reaction mixture is evaporating solvent on a rotary evaporator and analyzed with 1H NMR using CH2Br2 as an internal standard. Silica gel column chromatography with hexane/ ethyl acetate as the eluent affords the purified alkynylsilane product.

Reference： [1]Huang, Pan; Xu, Dawen; Reich, Robert M.; Kaiser, Felix; Liu, Boping; Kühn, Fritz E. [Tetrahedron Letters, 2019, vol. 60, # 24, p. 1574 - 1577]

66
[ 42472-69-5 ]
6-bromo-N,N-dimethyl-3-benzylnaphthalene-1-amine [ No CAS ]
1-(4-((5-(dimethylamino)-7-phenylnaphthalen-2-yl)ethynyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 100℃; for 32h; Inert atmosphere;	7 Synthesis of 1-(4-((5-(dimethylamino)-7-phenylnaphthalen-2-yl)ethynyl)phenyl)ethanone 0.20 mmol of 6-bromo-N,N-dimethyl-3-phenylnaphthalen-1-amine, 0.30 mmol of 4-(4-ethynylphenyl)ethanone, 0.01 mmol of Pd (PPh). )3Cl2, 0.01 mmol CuI, 0.40 mmol diisopropylamine, 1.0 mL THF was added to the reactor.Under a nitrogen atmosphere, heat to 100 ° C, stirring for 32 h, stop the reaction, cool to room temperature, wash with saturated ammonium chloride solution, then extract with dichloromethane, dry, distillate the solvent under reduced pressure, the crude product is separated by column chromatography The target product was obtained in a yield of 82%.

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN109912432, 2019, A Location in patent: Paragraph 0039-0041

67
[ 42472-69-5 ]
3-(4-bromophenyl)-N,N-dimethylnaphthalen-1-amine [ No CAS ]
1-[4-(2-{4-[4-(dimethylamino)naphthalen-2-yl]phenyl}ethynyl)phenyl]ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 100℃; for 30h; Inert atmosphere;	3 Synthesis of 1-(4-(4-(4-(dimethylamino)naphthalen-2-yl)phenyl)ethynyl)phenyl)ethanone 0.20 mmol of 3-(4-bromophenyl)-N,N-dimethylnaphthalen-1-amine, 0.26 mmol of 1-(4-ethynylphenyl)ethanone, 0.008 mmol of Pd (PPh)3Cl2, 0.01 mmol CuI, 0.40 mmol diisopropylamine, 1.0 mL THF was added to the reactor.Under a nitrogen atmosphere, heat to 100 ° C, stirring for 30 h, stop the reaction, cool to room temperature, wash with saturated ammonium chloride solution, then extract with dichloromethane, dry, distillate the solvent under reduced pressure, the crude product is separated by column chromatography The target product was obtained in a yield of 83%.

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN109912432, 2019, A Location in patent: Paragraph 0027-0029

68
[ 1514-82-5 ]
[ 42472-69-5 ]
1-(4-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Inert atmosphere; Schlenk technique;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 40℃; Schlenk technique; Inert atmosphere;	3. General Process for the Synthesis of 1a, 2a, 3a, 4a, 5a and 6a General procedure: A Schlenk flask was charged with Pd(PPh3)2Cl2 (2 mol %) and CuI (5 mol %) under N2 atmosphere.Dry triethyamine and 2-bromo-3,3,3-trifluoro-1-propene (1.2 equiv) were added subsequently followedby dropwise addition of phenylacetylene (1.0 equiv). The reaction mixture was stirred at 40 oC untilcompletion. The reaction was then quenched with saturated NH4Cl solution and extracted with pentane.Combined extracts were dried over Na2SO4 and solvent was removed under vacuum. The residue waspurified by column chromatography to afford the corresponding enyne 1a. All 1,3-enynes can beprepared in good yield by this procedure1-2.

Reference： [1]Dai, Dong-Ting; Li, Qi; Liu, Zheng-Li; Ma, Wei-Wei; Xu, Yun-He; Yang, Chao; Zhao, Meng [Organic Letters, 2020]
[2]Kuang, Zhijie; Chen, Haohua; Qiu, Jian; Ou, Zongliang; Lan, Yu; Song, Qiuling [Chem, 2020, vol. 6, # 9, p. 2347 - 2363]

69
[ 42472-69-5 ]
1-(4-(3-(4-ethynylphenyl)-3-hydroxybut-1-yn-1-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrabutylammomium bromide In dimethyl sulfoxide for 1 - 3h; Electrolysis;	General procedure for the synthesis of 2/4/7/9/11.- General procedure: To a solution of 0.5 mmol of 2/4/7/9/11 in DMSO (3 ml) in a threeneck round bottom flask fitted with platinum electrodes (1 cm × 1cm) and passed a constant current of 15 mA was passed for 1-3 h from an amperostate. Reaction was monitored by thin layer chromatography. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml), washed with brine(20 ml). The aqueous layer was extracted with ethyl acetate (30 ml).The combined ethyl acetate layer was washed with brine (20 ml).The organic layer was evaporated under reduced pressure. The crude products were purified by preparative TLC.

Reference： [1]Li, Qian-Yu; Swaroop, Toreshettahally R.; Wang, Heng Shan; Wang, Zi-Qiang [Journal of the Electrochemical Society, 2020, vol. 167, # 4]

70
[ 42472-69-5 ]
C₁₂H₁₀BrN₃O [ No CAS ]
C₂₂H₁₇N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine; triphenylphosphine In toluene at 100℃; for 5h;	3.3 Synthesis of compound 6 Dissolve 500 mg of compound 2 (3.47 mmol), 320 mg of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4, 0.278 mmol) and 1210 mg of compound 5 (4.16 mmol) in a mixture of toluene and diisopropylamine (from 20 mL of toluene) Mixed with 20mL of diisopropylamine), heated to reflux at 100 for 5 hours, after the reaction solution is cooled with a mixture of dichloromethane and water (such as dichloromethane and water volume ratio of 1: 1 mix Liquid) extraction twice, the organic phase was washed with saturated brine, and then dried over anhydrous sodium sulfate, filtered, and spin-dried, and the crude product obtained was eluted with a normal phase silica gel column (eluent is a mixture of petroleum ether and dichloromethane Liquid, in which the volume ratio of the two is petroleum ether: dichloromethane = 1: 1), to obtain 440 mg of compound 6 (yellow solid, yield 36%).
36%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine In toluene at 100℃; for 5h;

Reference： [1]Current Patent Assignee: GUANGZHOU UNIVERSITY OF CHINESE MEDICINE - CN111072466, 2020, A Location in patent: Paragraph 0080-0081; 0086-0087
[2]Chen, Huihong; Huang, Xin-An; Liang, Yunshi; Wu, Haiting; Xiang, Lingling; Zhang, Jing; Zhao, Hailong [Organic and biomolecular chemistry, 2020, vol. 18, # 27, p. 5120 - 5124]

71
[ 42472-69-5 ]
[ 1671-88-1 ]
6-(4-ethynylphenyl)-3-(pyridin-2-yl)-7H-pyrido[2,1-d][1,2,4]triazolo[4,3-b][1,2,5]triazepin-8-ium iodide [ No CAS ]

Reference： [1]Green Chemistry,2020,vol. 22,p. 3111 - 3116

72
[ 42472-69-5 ]
(E)-1-(1-chloro-2-iodo)-1-[4-(acetyl)]styrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 4-ethynylacetophenone With acetic acid; lithium chloride; lithium iodide In dichloromethane at 0℃; for 0.166667h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 13h;	8 Take 4-acetylphenylacetylene (28mg, 0.2mmol), lithium iodide (32mg, 0.24mmol), lithium chloride (10mg, 0.24mmol) into a 10mL reaction flask, then add 1mL of acetic acid and 0.5mL of dichloromethane , Cool to 0°C and stir for 10 minutes, add m-chloroperoxybenzoic acid (50mg, 0.24 mmol), stir for 1 hour, slowly increase the temperature to room temperature, and continue the reaction for 12 hours. After the reaction is over, add ethyl acetate 10 mL of the ester was added with 5 mL of water for extraction, the organic phase was dried with anhydrous sodium sulfate, and 50 mg of the target compound was obtained by column chromatography. The yield of the target compound was determined to be 83%.

Reference： [1]Current Patent Assignee: YANCHENG INSTITUTE OF TECHNOLOGY - CN111807938, 2020, A Location in patent: Paragraph 0090-0095

73
[ 42472-69-5 ]
[ 824-79-3 ]
1-(4-acetylphenyl)-2-tosylethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: sodium 4-methylbenzenesulfinate With 2-Picolinic acid; copper(l) iodide; trimethylsilylazide In methanol for 0.0833333h; Green chemistry; Stage #2: 4-ethynylacetophenone With oxygen In methanol at 25 - 28℃; Irradiation; Green chemistry;

Reference： [1]Charpe, Vaibhav Pramod; Das, Deb Kumar; Hwang, Kuo Chu; Hwu, Jih Ru; Lin, Chun-Cheng; Pampana, V. K. K.; Sagadevan, Arunachalam [Green Chemistry, 2021, vol. 23, # 10, p. 3569 - 3574]

74
[ 111-88-6 ]
[ 201230-82-2 ]
[ 42472-69-5 ]
S-octyl (E)-3-(4-acetylphenyl)prop-2-enethioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With palladium(II) trifluoroacetate; 5-chloro-2-hydroxybenzoic acid; boric acid; bis[2-(diphenylphosphino)phenyl] ether In acetonitrile at 110℃; for 14h; Autoclave; regioselective reaction;

Reference： [1]Ai, Han-Jun; Lu, Wangyang; Wu, Xiao-Feng [Angewandte Chemie - International Edition, 2021, vol. 60, # 31, p. 17178 - 17184][Angew. Chem., 2021, vol. 133, # 31, p. 17315 - 17321]

75
[ 111-88-6 ]
[ 201230-82-2 ]
[ 42472-69-5 ]
S-octyl 2-(4-acetylphenyl)prop-2-enethioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With trifuran-2-yl-phosphane; 5-chloro-2-hydroxybenzoic acid; boric acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In acetonitrile at 120℃; for 14h; Autoclave; regioselective reaction;

Reference： [1]Ai, Han-Jun; Lu, Wangyang; Wu, Xiao-Feng [Angewandte Chemie - International Edition, 2021, vol. 60, # 31, p. 17178 - 17184][Angew. Chem., 2021, vol. 133, # 31, p. 17315 - 17321]

76
[ 591-50-4 ]
[ 201230-82-2 ]
[ 42472-69-5 ]
[ 73183-34-3 ]
C₂₉H₃₈B₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With {(π-CH2CHCH2)PdCl}2; chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene; <i>tert</i>-butyl alcohol at 20 - 80℃; for 12h; Inert atmosphere; Autoclave;	2.2.2 General procedure II General procedure: A vial (4 mL) was charged with (η3-C3H5-PdCl)2 (0.7 mol%),DPEPhos (2.8 mol%), IMesCuCl (5.0 mol%), B2pin2(76.2 mg, 1.5 equiv.), NaOtBu (28.8 mg, 1.5 equiv.), and astirring bar. The vial was closed by PTFE/white rubberseptum (Wheaton 13 mm Septa) and phenolic cap andconnected with atmosphere with a needle. The vial wasevacuated under vacuum and recharged with argon for threetimes. Then, toluene (1.0 mL) was injected under argon byusing a syringe. After that aryl iodides 1 (0.25 mmol, 1.25equiv.), and internal alkynes 2 (0.2 mmol, 1.0 equiv.) wereadded, and the vial (or several vials) was placed in an alloyplate, which was transferred into a 300 mL autoclave of the4560 series from Parr Instruments. After flushing the autoclavethree times with CO, a pressure of 10 bar of CO wasadjusted at ambient temperature. Then, the reaction wasperformed for 12 h at 80 °C. When the reaction was completed,the autoclave was cooled down with ice water toroom temperature and the pressure was released carefully.The solution was then filtered through celite and concentratedin vacuo. After that NaBH4 (0.6 mmol, 3 equiv.)and CH3OH (1.0 mL) were added into the residue, the reactionwas stirred at room temperature for 1.0 h, and then the crude reaction mixture was diluted with Et2O (10 mL)and H2O (5 mL). The organic phase was separated, and theaqueous layer was extracted twice with Et2O. The combinedorganic layers were washed with brine, dried over MgSO4,filtered and concentrated on a rotary evaporator. Finally, theresidue was purified by silica gel chromatography (hexane/ethyl acetate) to afford the corresponding products 3ax-3bb (Reaction 2).

Reference： [1]Yuan, Yang; Wu, Fu-Peng; Spannenberg, Anke; Wu, Xiao-Feng [Science China Chemistry, 2021, vol. 64, # 12, p. 2142 - 2153]

77
[ 22979-35-7 ]
[ 42472-69-5 ]
C₁₉H₁₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With ferric(III) bromide; palladium diacetate; triethylamine hydrobromide; tert-butyldiphenylphosphine In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;

Reference： [1]Guo, Hongyu; Zhang, Sheng; Yu, Xiaoqiang; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming [ACS Catalysis, 2021, vol. 11, # 17, p. 10789 - 10795]

78
[ 40426-99-1 ]
[ 42472-69-5 ]
dimethyl 3-(4-acetylphenyl)-4-(bromomethyl)-cyclopent-2-ene-1,1-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 20h; Inert atmosphere; Irradiation;	3.2. General Procedure for ATRA/ATRC Reaction General procedure: A Pyrex test tube from Corning (Tokyo, Japan) (12.5 cm 1.6 cm) containing amixture of alkyne 1 or alkene 4 (1.0 equiv, 0.1 mmol), -halogencarbonyl 2 (3.0 equiv,0.3 mmol) and N,N-diisopropylethylamine (1.0 equiv, 0.1 mmol) in ethyl acetate (0.75 mL)was degassed via FPT cycling three times and backfilled with Ar. The tube was placed ca.0.5 cm from 3W420 nm LED. The resulting solution was stirred at ambient temperaturefor 20 h. The residue was concentrated in vacuo. The resulting mixture was purified byflash column chromatography on silica gel to yield product 3, 5 or 6.

Reference： [1]Itoh, Akichika; Matsuo, Kazuki; Yamaguchi, Eiji; Yoshitake, Tadashi [Molecules, 2021, vol. 26, # 22]

79
[ 35107-79-0 ]
[ 42472-69-5 ]
1-[(E)-2-(4-acetylphenyl)ethenyl]-1,1,2,2-tetramethyl-2-phenyldisilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 20℃; for 96h; regioselective reaction;	4.3.16. Synthesis of 1-[(E)-2-(4-acetylphenyl)ethenyl]- 1,1,2,2-tetramethyl-2-phenyldisilane ( E-2i ) A mixture of 1 (95 mg, 0.49 mmol), 4-ethynylacetophenone (111 mg, 0.77 mmol), RuHCl(CO)(PPh 3 ) 3 (24 mg, 0.025 mmol) and tridecane (56 mg, 0.30 mmol) in toluene (2 mL) was stirred at room temperature for 4 days. After evaporation of the solvent, the residue was separated by column chromatography over silica gel (eluent: hexane-ethyl acetate (20:1)) to give 2i (106 mg, 64%, E / Z = 96/4) as a colorless oil. E -2i . 1 H NMR (600 MHz, CDCl 3 ): δ0.23 (s, 6H), 0.39 (s, 6H), 2.60 (s, 3H), 6.63 (d, 1H, J = 18.6 Hz), 6.80 (d, 1H, J = 18.6 Hz), 7.33-7.35 (m, 3H), 7.44-7.47 (m, 4H), 7.92 (d, 2H, J = 8.4 Hz). 13 C NMR (151 MHz, CDCl 3 ): δ-4.1, -3.7, 26.8, 126.5, 127.9, 128.7, 128.9, 132.5, 134.0, 136.3, 139.1, 142.8, 142.9, 197.8. 29 Si NMR (119 MHz, CDCl 3 ): δ-23.3, -20.9. IR (NaCl): 3070, 2950, 1680, 1600, 1430, 1410, 1360, 1270, 830, 800, 730, 700 cm -1 . MS (EI, 70 eV): m/z 338 (M + , 11), 323 (10), 260 (52), 245 (12), 239 (12), 207 (13), 187 (10), 177 (10), 145 (12), 137 (21), 135 (100), 75 (18), 73 (13), 59 (16). HRMS (FD): found 338.1531, calcd for C 20 H 26 OSi 2 338.1522.

Reference： [1]Egawa, Saki; Kanno, Ken-ichiro; Kyushin, Soichiro; Mita, Masato; Noguchi, Seiya; Ono, Yukie; Otsuka, Naoki [Journal of Organometallic Chemistry, 2022, vol. 961]

80
[ 35107-79-0 ]
[ 42472-69-5 ]
1-[1-(4-acetylphenyl)ethenyl]-1,1,2,2- tetramethyl-2-phenyldisilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: 1,1,2,2-tetramethyl-2-phenyldisilane; 4-ethynylacetophenone With [RuCl₂pentamethylcyclopentadiene]_n In toluene at 20℃; for 41h; Stage #2: With N,N,N,N,-tetramethylethylenediamine; copper(l) chloride In acetone at 20℃; for 1h; regioselective reaction;	4.3.23. Synthesis of 1-[1-(4-acetylphenyl)ethenyl]-1,1,2,2- tetramethyl-2-phenyldisilane ( α-2i ) A mixture of 1 (95 mg, 0.49 mmol), 4-ethynylacetophenone (107 mg, 0.742 mmol), [Cp RuCl 2 ] n (9.4 mg, 0.031 mmol) and tridecane (59 mg, 0.32 mmol) in toluene (2 mL) was stirred at room temperature for 41 h. After evaporation of the solvent, the residue was separated by column chromatography over silica gel (eluent: hexane-ethyl acetate (20:1)). The crude product was dis- solved in acetone (2 mL), and TMEDA (10 mg, 0.086 mmol) and copper(I) chloride (8 mg, 0.08 mmol) were added. The mixture was stirred at room temperature for 1 h in air. After evaporation of the solvent, the residue was separated by column chromatography over silica gel (eluent: hexane-ethyl acetate (20:1)) to give 2i (87 mg, 53%, α/ E = 98/2) as a colorless oil. α-2i . 1 H NMR (600 MHz, CDCl 3 ): δ0.23 (s, 6H), 0.30 (s, 6H), 2.58 (s, 3H), 5.59 (d, 1H, J = 2.7 Hz), 5.87 (d, 1H, J = 2.7 Hz), 7.10 (d, 2H, J = 8.4 Hz), 7.28-7.32 (m, 3H), 7.36-7.38 (m, 2H), 7.81 (d, 2H, J = 8.4 Hz). 13 C NMR (151 MHz, CDCl 3 ): δ-3.6, -3.0, 26.7, 127.1, 127.9, 128.4, 128.7, 129.0, 133.9, 135.2, 138.8, 150.3, 151.9, 197.9. 29 Si NMR (119 MHz, CDCl 3 ): δ-21.1, -20.3. IR (NaCl): 3070, 2950, 2890, 1680, 1600, 1430, 1400, 1360, 1270, 1110, 850, 830, 790, 770, 730, 700 cm -1 . MS (EI, 70 eV): m/z 338 (M + , 9), 239 (15), 177 (47), 135 (100), 130 (11). HRMS (FD): found 338.1522, calcd for C 20 H 26 OSi 2 338.1522.

Reference： [1]Egawa, Saki; Kanno, Ken-ichiro; Kyushin, Soichiro; Mita, Masato; Noguchi, Seiya; Ono, Yukie; Otsuka, Naoki [Journal of Organometallic Chemistry, 2022, vol. 961]

81
[ 42472-69-5 ]
S-(trifluoromethyl)thianthrenium triflate [ No CAS ]
[ 6462-50-6 ]
(E)-1-(4-(3,3,3-trifluoro-1-((4-methoxyphenyl)sulfonyl)prop-1-en-1-yl)phenyl)ethan-1-one [ No CAS ]