Name: 103-64-0|(2-Bromovinyl)benzene|95%
Brand: Ambeed
SKU: A117091
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1
[ 29786-93-4 ]
[ 103-64-0 ]
1-phenylhex-1-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis-tributylphosphine palladium⁽⁰⁾ In toluene at 20℃; Schlenk technique; Inert atmosphere;	General procedure for the Pd-catalysed cross-coupling with alkyllithium reagents (Caution Some organolithium reagents can be pyrophoric.) In a dry Schlenk flask, Pd[P(t-Bu)3]2 (5 mol%, 0.015 mmol, 7.66 mg) and the substrate (0.3 mmol) were dissolved in 2 ml of dry toluene under an inert atmosphere. The corresponding lithium reagent (1.2 equiv.) was diluted with toluene to reach a concentration of 0.36 M. This solution was slowly added over 1 h using a syringepump. After the addition was completed, a saturated aqueous solution of NH4Cl was added and the mixture was extracted three times with diethyl ether. The organic phases were collected, and solvent evaporation under reduced pressure afforded the crude product, which was then purified by column chromatography.
	With Petroleum ether

Reference： [1]Giannerini, Massimo; Fananas-Mastral, Martin; Feringa, Ben L. [Nature Chemistry, 2013, vol. 5, # 8, p. 667 - 672]
[2]Marvel; Hager; Coffman [Journal of the American Chemical Society, 1927, vol. 49, p. 2326]

2
[ 103-64-0 ]
[ 538-81-8 ]

Reference： [1]Journal of Organometallic Chemistry,1986,vol. 303,p. 131 - 138
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1902,vol. 135,p. 1346
Annales de Chimie (Cachan, France),1907,vol. <8> 10,p. 168
[3]Recueil des Travaux Chimiques des Pays-Bas,1926,vol. 45,p. 358
Recueil des Travaux Chimiques des Pays-Bas,1928,vol. 47,p. 734

3
[ 103-64-0 ]
[ 536-74-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium-t-butoxide
92%	With sodium bis-(trimethyl-silyl)amide In 1,2-dimethoxyethane at 20℃; for 1h;
90.8%	With potassium hydroxide; zinc powder at 120℃; for 6h; Inert atmosphere;	1-6 Example six In a 250ml three-necked flask, add 183g (1mol) of bromostyrene, 39g (0.6mol) of zinc powder, 28g (0.5mol) of potassium hydroxide, nitrogen protection, stir evenly, heat to 120°C for reaction for 6 hours,The reaction was stopped, filtered, the filter cake was drained, the filtrate was distilled at atmospheric pressure, and 92.6 g of fractions at 140°C to 143°C were collected, namely the product phenylacetylene, with a yield of 90.8% and a GC purity of 99.5%. The remaining residues were distilled under reduced pressure, the pressure was -0.095MP, and 12.6 g of fractions at 100°C to 105°C were collected, namely bromo styracene, which was applied to the next batch of experiments.

86%	With potassium-t-butoxide In 1-methyl-pyrrolidin-2-one at 50℃; for 0.166667h; Schlenk technique; Inert atmosphere;
	With potassium hydroxide at 200 - 215℃;
	With petroleum; sodium amide at 160℃;
	With ammonia; sodium amide
	With diethyl ether; sodium amide; aniline
	With potassium hydroxide
	With phosphorus pentoxide
	With fired clay
	With metal chloride
	With potassium hydroxide; ethanol at 125 - 130℃;
	With potassium hydroxide at 200℃; Erhitzen des Reaktionsgemisches auf 230grad;
	With potassium hydroxide; ethanol Reinigung durch Destillation im Vakuum;
	Multi-step reaction with 2 steps 1: diethyl ether; sodium 2: water / 120 °C / im geschlossenen Rohr
	With tripotassium phosphate tribasic In ethanol at 80℃;	Synthesis of acetylenes from vicinal dibromides General procedure: A mixture of vicinal dibromide (5 mmol), anhydrous K3PO4 (5 mmol), PEG-900 (1.25 mmol), and EtOH (10 mL) was stirred at 80 °C. The progress of the reaction was monitored by analysis of the samples using TLC and gas chromatography. When the vicinal dibromide had been completely converted into the monobromo product, a second portion of K3PO4 (5 mmol) was added.Following completion of the reaction the mixture was filtered and the filtrate was diluted with CH2Cl and washed several times with H2O. The organic phase was dried over MgSO4 and evaporated under vacuum to afford a mixture of product and the monobromo derivative. The acetylene was separated by vacuum distillation. The identity and purity of the products were confirmed by GC-MS and 1H NMR spectroscopy.

Reference： [1]Heredia, Adrián A.; Peñéñory, Alicia B. [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 910 - 918]
[2]Li, Minyan; Gutierrez, Osvaldo; Berritt, Simon; Pascual-Escudero, Ana; YeÅlçimen, Ahmet; Yang, Xiaodong; Adrio, Javier; Huang, Georgia; Nakamaru-Ogiso, Eiko; Kozlowski, Marisa C.; Walsh, Patrick J. [Nature Chemistry, 2017, vol. 9, # 10, p. 997 - 1004]
[3]Current Patent Assignee: SHANDONG BOYUAN PHARMACEUTICAL CHEMISTRY - CN114181028, 2022, A Location in patent: Paragraph 0025-0036
[4]Zaid, Yassir; Mboyi, Clève Dionel; Drapeau, Martin Pichette; Radal, Léa; Chahdi, Fouad Ouazzani; Rodi, Youssef Kandri; Ollevier, Thierry; Taillefer, Marc [Organic Letters, 2019, vol. 21, # 6, p. 1564 - 1568]
[5]Rupe; Rinderknecht [Justus Liebigs Annalen der Chemie, 1925, vol. 442, p. 66] Hessler [Journal of the American Chemical Society, 1922, vol. 44, p. 425]
[6]Truchet [Annales de Chimie (Cachan, France), 1931, vol. <10>16, p. 396][Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1930, vol. 191, p. 855]
[7]Vaughn [Journal of the American Chemical Society, 1934, vol. 56, p. 2064] Vaughn; Vogt; Nieuwland [Journal of the American Chemical Society, 1934, vol. 56, p. 2120]
[8]Bodroux [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1939, vol. 208, p. 1023]
[9]Dufraisse [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1920, vol. 171, p. 961][Annales de Chimie (Cachan, France), 1922, vol. <9> 17, p. 162]
[10]Hein; Meyer [Fresenius Zeitschrift fur Analytische Chemie, 1927, vol. 72, p. 30]
[11]Hein; Meyer [Fresenius Zeitschrift fur Analytische Chemie, 1927, vol. 72, p. 30]
[12]Hein; Meyer [Fresenius Zeitschrift fur Analytische Chemie, 1927, vol. 72, p. 30]
[13]Manchot [Justus Liebigs Annalen der Chemie, 1912, vol. 387, p. 291]
[14][Organic Syntheses 2 <New York 1922>, S. 67]
[15]Straus [Justus Liebigs Annalen der Chemie, 1905, vol. 342, p. 257]
[16]Glaser [Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 166]
[17]Location in patent: experimental part Shenawi-Khalil, Sanaa; Sonavane, Sachin U.; Sasson, Yoel [Tetrahedron Letters, 2012, vol. 53, # 18, p. 2295 - 2297]

4
[ 6286-30-2 ]
[ 103-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	With water
	With aqueous alkali
	With ethanol; potassium acetate

	With sodium carbonate higher-melting form;
	With sodium carbonate higher-melting form;
	With sodium carbonate at 100℃;

Reference： [1]Erlenmeyer [Chemische Berichte, 1880, vol. 13, p. 306] Glaser [Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 166] Erlenmeyer [Zeitschrift fur Chemie, 1864, p. 549]
[2]Sudborough; Thompson [Journal of the Chemical Society, 1903, vol. 83, p. 673]
[3]Straus [Chemische Berichte, 1909, vol. 42, p. 2878]
[4]Dufraisse [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1920, vol. 171, p. 961][Annales de Chimie (Cachan, France), 1922, vol. <9> 17, p. 162]
[5]Nef, J.V. [Justus Liebigs Annalen der Chemie, 1899, vol. 308, p. 264 - 328]
[6]Nef, J.V. [Justus Liebigs Annalen der Chemie, 1899, vol. 308, p. 264 - 328]

5
[ 375-80-4 ]
[ 103-64-0 ]
[ 55009-93-3 ]

Reference： [1]Journal of Organic Chemistry,1975,vol. 40,p. 810 - 811

6
[ 375-80-4 ]
[ 103-64-0 ]
[ 55009-89-7 ]

Reference： [1]Journal of Organic Chemistry,1975,vol. 40,p. 810 - 811

7
[ 84-51-5 ]
[ 103-64-0 ]
[ 96809-97-1 ]

Reference： [1]Bulletin de la Societe Chimique de France,1963,p. 1707 - 1709

8
[ 2386-58-5 ]
[ 103-64-0 ]
[ 57185-68-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine In N,N-dimethyl-formamide at 140℃; for 24h;

Reference： [1]Hirooka, Syuzi; Tanbo, Yuzi; Takemura, Katsuya; Nakahashi, Hironori; Matsuoka, Tsuyoshi; Kuroda, Shigeyasu [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 4, p. 1431 - 1433]

9
[ 124-38-9 ]
[ 103-64-0 ]
[ 621-82-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique; Stage #2: bromostyrene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 16h; Schlenk technique;	25 Preparation of benzoic acid General procedure: In a Schlenk (50 mL) reaction flask with a carbon dioxide balloon attached to a branch tube, add Cu (OAc) 2.H2O (0.0125 mmol), 1,2-bis (diphenylphosphine) benzene (0.018 mmol), and 1,4 -Dioxane (2.0mL), PMHS (2.5mmol) was added under stirring, and then the reaction flask was placed in an oil bath at 60 ° C for 25min to react under carbon dioxide atmosphere, followed by toluene (8mL) and bromobenzene (1.0 mmol), Pd (OAc) 2 (0.03 mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.06 mmol), Et3N (2.5 mmol, 2.5 equiva.), The carbon dioxide was then removed and reacted at 100 ° C until the raw bromobenzene disappeared. After cooling to room temperature, sodium hydroxide solution (1M, 10.0mL) was added, stirred for 10min, and filtered. The solid was washed three times with water, and the filtrate was washed with ethyl acetate ( 2 × 10mL) left after extraction, the aqueous layer was adjusted to pH 1-2 with hydrochloric acid solution (1M), extracted with ethyl acetate (3 × 15mL), dried over anhydrous sodium sulfate,The solvent was removed to give benzoic acid. Yield, 65%.
80%	In N,N-dimethyl-formamide at 5℃; electrochemical oxidation;

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Dalian Institute of Chemical Physics (in: CAS) - CN110724047, 2020, A Location in patent: Paragraph 0085-0086; 0165-0167; 0177
[2]Sock, Oumar; Troupel, Michel; Perichon, Jacques [Tetrahedron Letters, 1985, vol. 26, # 12, p. 1509 - 1512]

10
[ 201230-82-2 ]
[ 103-64-0 ]
[ 555-75-9 ]
[ 103-36-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	In n-heptane at 150℃; for 14h;
66%	In n-heptane at 150℃; for 14h; effect of use of var. catalyzer, and temp.;

Reference： [1]Alper, Howard; Antebi, Shlomo; Woell, James B. [Angewandte Chemie, 1984, vol. 96, # 9, p. 710 - 711]
[2]Alper, Howard; Antebi, Shlomo; Woell, James B. [Angewandte Chemie, 1984, vol. 96, # 9, p. 710 - 711]

11
[ 103-64-0 ]
[ 120120-26-5 ]
[ 55009-95-5 ]
(E)-3,3,3-trifluoro-1-phenylpropene [ No CAS ]
[ 74031-42-8 ]

Yield	Reaction Conditions	Operation in experiment
14%	With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h; Yields of byproduct given;
14 (unit not given)	With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h; Yield given;

Reference： [1]Urata, Hisao; Fuchikami, Takamasa [Tetrahedron Letters, 1991, vol. 32, # 1, p. 91 - 94]
[2]Urata, Hisao; Fuchikami, Takamasa [Tetrahedron Letters, 1991, vol. 32, # 1, p. 91 - 94]

12
[ 103-64-0 ]
[ 100-42-5 ]
[ 1445-78-9 ]
[ 612-94-2 ]
[ 536-74-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 1523 - 1528
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1743 - 1749

13
[ 103-64-0 ]
[ 101349-79-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(I) oxide; <i>L</i>-proline; potassium iodide In ethanol at 110℃; for 29h; Schlenk technique; Inert atmosphere; Green chemistry; stereospecific reaction;	1 2-bromo-1-phenylethylene (45.7625 mg, 0.25 mmol), potassium iodide (KI, 124.5 mg, 0.75 mmol), cuprous oxide (3.6 mg, 0.025 mmol), L-proline (5.8 mg, 0.05 mmol) ) And added sequentially to a 25 mL Schlenk flask, and purified ethanol (3 mL) was added and allowed to react in a 110 ° C oil bath for 29 h. After completion of the reaction, the reaction solution was filtered through a silica gel column into a 10 mL volumetric flask and the volume of the solution was quantified to the specified scale with ethyl acetate. The yield of 2-iodophenylethylene was 82% using gas chromatography.
77%	Stage #1: bromostyrene With n-butyllithium; zirconocene dichloride In tetrahydrofuran at -78 - 20℃; Stage #2: With iodine In tetrahydrofuran at -20 - 20℃; Further stages.;
64%	Stage #1: bromostyrene With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: With 1,1,1-trifluoro-2-iodoethane In tetrahydrofuran

With ethene; potassium iodide In various solvent(s) at 50℃; for 1h; electrolysis; Yield given;

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN104829419, 2017, B Location in patent: Paragraph 0032-0035
[2]Liard; Marek [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 7218 - 7220]
[3]Blackmore, Ian J.; Boa, Andrew N.; Murray, Ernest J.; Dennis, Michael; Woodward, Simon [Tetrahedron Letters, 1999, vol. 40, # 36, p. 6671 - 6672]
[4]Meyer, Gilbert; Rollin, Yolande; Perichon, Jacques [Tetrahedron Letters, 1986, vol. 27, # 30, p. 3497 - 3500]

14
[ 2425-28-7 ]
[ 103-64-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium hydrogensulfate; hydroquinone In water at 150 - 185℃;

Reference： [1]Cervinka, Otakar; Dudek, Vaclav; Fabryova, Anna; Kolar, Jiri; Lukac, Juraj; et al. [Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 10, p. 2748 - 2752]

15
[ 103-64-0 ]
[ 108-98-5 ]
[ 16619-61-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N,N-diethylaniline In N,N-dimethyl-formamide at 70℃; for 23h;
	at 140 - 160℃; Yield given;
80 % Chromat.	With sodium hydroxide; trans-bromo(phenyl)bis(triphenylphosphine)palladium(II); cetyltributylphosphonium bromide; triphenylphosphine In toluene at 80℃; for 9h;

Reference： [1]Yatsumonji, Yasutaka; Okada, Orie; Tsubouchi, Akira; Takeda, Takeshi [Tetrahedron, 2006, vol. 62, # 42, p. 9981 - 9987]
[2]Kuznetsova, M. A.; Korchevin, N. A.; Deryagina, E. N.; Voronkov, M. G. [Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 6, p. 1136 - 1140][Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 6, p. 1255 - 1260]
[3]Foa, M.; Santi, R.; Garavaglia, F. [Journal of Organometallic Chemistry, 1981, vol. 206, # 3, p. C29 - C32]

16
[ 103-64-0 ]
[ 252652-84-9 ]
(2S,4S,2'E)-4-isobutyl-2-(1'-methylene-3'-phenylprop-2'-enyl)-N-(4-methylphenylsulfonyl)azetidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 70℃;
81%	With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.75h;

Reference： [1]Anzai, Miyuki; Toda, Ayako; Ohno, Hiroaki; Takemoto, Yoshiji; Fujii, Nobutaka; Ibuka, Toshiro [Tetrahedron Letters, 1999, vol. 40, # 41, p. 7393 - 7397]
[2]Ohno; Anzai; Toda; Ohishi; Fujii; Tanaka; Takemoto; Ibuka [Journal of Organic Chemistry, 2001, vol. 66, # 14, p. 4904 - 4914]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; <i>tert</i>-butyl alcohol In water Irradiation; oxidation in air-saturated solution, pH ca.7;

18
[ 103-64-0 ]
[ 588-72-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With fluorescein In 1,4-dioxane at 20℃; for 24h; Inert atmosphere; Irradiation; stereoselective reaction;
70%	With sodium hydroxide In isopropyl alcohol for 2h; Reflux;
	With sodium hydroxide In isopropyl alcohol Heating;

2.55 g	With sodium hydroxide In isopropyl alcohol for 1.5h; Reflux; Inert atmosphere;
	With sodium hydroxide In water; isopropyl alcohol for 1.5h; Inert atmosphere; Reflux;	2. General Procedure 2: Synthesis of (E)-vinyl bromide synthesis from aldehydes. General procedure: Step 3: Selective destruction of the (Z)-isomer as reported by Dolby. The crude product (~20.0 mmol, 100 mol %) from the previous step was dissolved in i-PrOH (30mL). Solid NaOH (17.0 mmol, 85 mol %) was added and the mixture was heated to reflux for 1.5 hours. The reaction mixture was cooled to room temperature, diluted with pentane (100 mL), and partitioned with distillated H2O (2 × 100 mL). The organic phase was collected, and washed with an aqueous solution of HCl (1M, 75 mL), dried over Na2SO4. The solvent was removed under reduced pressure. The crude material was purified by flash chromatography.
	With sodium hydroxide In isopropyl alcohol Reflux;
	With sodium hydroxide In isopropyl alcohol Reflux;

Reference： [1]Zhang, Hao; Xu, Qing; Yu, Lei; Yu, Shouyun [European Journal of Organic Chemistry, 2020, vol. 2020, # 10, p. 1472 - 1477]
[2]Mueller, Daniel; Alexakis, Alexandre [Organic Letters, 2012, vol. 14, # 7, p. 1842 - 1845]
[3]Cannes; Condon; Durandetti; Perichon; Nedelec [Journal of Organic Chemistry, 2000, vol. 65, # 15, p. 4575 - 4583]
[4]Liu, Jiandong; Ren, Qinghua; Zhang, Xinghua; Gong, Hegui [Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15544 - 15548][Angew. Chem., 2016, vol. 128, # 50, p. 15773 - 15777]
[5]Gu, Jun; Qiu, Canbin; Lu, Wenbin; Qian, Qun; Lin, Kunhua; Gong, Hegui [Synthesis, 2017, vol. 49, # 8, p. 1867 - 1873]
[6]Yu, Weijie; Chen, Long; Tao, Jiasi; Wang, Tao; Fu, Junkai [Chemical Communications, 2019, vol. 55, # 42, p. 5918 - 5921]
[7]Zhao, Jiangui; Zheng, Xueli; Tao, Shaokun; Zhu, Yuxin; Yi, Jiwei; Tang, Songbai; Li, Ruixiang; Chen, Hua; Fu, Haiyan; Yuan, Maolin [Organic Letters, 2021, vol. 23, # 15, p. 6067 - 6072]

19
[ 103-64-0 ]
[ 82598-07-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With D-Glucose; gold(III) acetate; tetra(n-butyl)ammonium hydroxide In water monomer at 90℃; for 15h;
85%	With palladium diacetate; sodium hydroxide; agarose In water monomer at 90℃; for 12h;
64%	With palladium diacetate; sodium hydroxide; agarose In water monomer at 90℃; for 12h;

52%	Stage #1: bromostyrene With magnesium In tetrahydrofuran at 0℃; for 1h; Stage #2: With synthetic air; cobalt(II) chloride In tetrahydrofuran at 0℃; for 0.5h;
30%	With Ni(PPh<SUB>3</SUB>)<SUB>2</SUB>Cl<SUB>2</SUB>; sodium hydride; triphenylphosphine In toluene at 70 - 90℃;
16%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; methyl 4-iodobenzoate; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium(II) chloride; zinc powder In tetrahydrofuran at 20℃; for 2.5h; Schlenk technique; Sealed tube; Inert atmosphere;
10%	With potassium fluoride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1-bromo-4-methoxy-benzene; N,N-dimethyl acetamide; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium(II) chloride; zinc powder at 0℃; for 1h; Schlenk technique; Sealed tube; Inert atmosphere;

Reference： [1]Monopoli, Antonio; Cotugno, Pietro; Palazzo, Gerardo; Ditaranto, Nicoletta; Mariano, Bruno; Cioffi, Nicola; Ciminale, Francesco; Naccia, Angelo [Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2777 - 2788]
[2]Location in patent: experimental part Firouzabadi, Habib; Iranpoor, Nasser; Kazemi, Faezeh [Journal of Molecular Catalysis A: Chemical, 2011, vol. 348, # 1-2, p. 94 - 99]
[3]Chen, Shaohang; Cui, Chengsen; Duan, Peigao; Hollmann, Frank; Li, Huanhuan; Wever, Ron; Younes, Sabry H. H.; Zhang, Wuyuan [ACS Catalysis, 2022, vol. 12, # 8, p. 4554 - 4559]
[4]Location in patent: scheme or table Mayer, Matthias; Czaplik, Waldemar Maximilian; Jacobi Von Wangelin, Axel [Synlett, 2009, # 18, p. 2919 - 2923]
[5]Lin; Hong [Journal of Organic Chemistry, 2001, vol. 66, # 8, p. 2877 - 2880]
[6]Liu, Jiandong; Ren, Qinghua; Zhang, Xinghua; Gong, Hegui [Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15544 - 15548][Angew. Chem., 2016, vol. 128, # 50, p. 15773 - 15777]
[7]Liu, Jiandong; Ren, Qinghua; Zhang, Xinghua; Gong, Hegui [Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15544 - 15548][Angew. Chem., 2016, vol. 128, # 50, p. 15773 - 15777]

20
[ 103-64-0 ]
[ 536-74-3 ]
1,4-diphenylbut-3-en-1-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With piperidine; silica-supported palladium catalyst at 70℃; for 0.5h;
73%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetra-n-butylammoniumfluoride trihydrate In tetrahydrofuran at 20℃; Inert atmosphere;
66%	With sodium hydroxide; palladium dichloride at 20 - 80℃; for 3h; Green chemistry;	General procedure for the sonogashira couplingreaction of aryl halides and phenylacetyenein the presence of PdCl2/DPPPEG200 in PEG200 General procedure: A round-bottom flask was charged with phenylacetylene(1.5 mmol, 0.16 mL), NaOH (1.5 mmol, 100 mg), PEG200(2 mL), and aryl halide (1.0 mmol). To this mixture,3.0 mol% of PdCl2 and 8.0 mol% of DPPPEG200 wereadded. The reaction mixture was placed in an 80 C oilbath and stirred to complete. The completion of the reactionwas monitored by TLC. After completion of reaction,the mixture was cooled to room temperature, and the catalystwas removed by addition of Et2O and then centrifugated.The isolated catalyst was dried and reused. Thefiltered solution was evaporated reduced pressure, and theexpected product was purified by column chromatographyover silica gel [60 Merck (230-240 mesh)] using petroleumether/ethyl acetate (5:1) as eluent to afford the product withhigh purity in 58-95 % yield.

64%	With potassium carbonate for 5.5h; Heating; Green chemistry;	General Procedure for the Sonogashira Coupling Reaction of Aryl Halides and Phenylacetyenein the Presence of Pd(0)/SDPP General procedure: A round-bottom flask was charged with phenylacetylene (0.75 mmol, 0.08 mL), K2CO3 (0.75 mmol, 100 mg), PEG 200 (1 mL), and aryl halide (0.5 mmol). To this mixture, Pd(0) nano-catalyst supported on SDPP (1.5 mol-%, 3.0 mg) prepared according to our previous report [13] was added. In the case of aryl iodides and activated aryl bromides, the reaction mixture was placed in a 100 °C oil bath; and in the case of the less active and deactivated aryl bromides and chlorides, the reaction mixture was placed in a 120 °C oil bath. After completion of the reaction, the catalyst was removed by centrifugation and the remaining mixture was extracted with ethyl acetate (310 mL) and water several times and dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure, and then purified by column chromatography over silica gel 60 (230-240 mesh; Merck) using petroleum ether/ethyl acetate (5 : 1) as eluent to afford the product with high purity in 51-95% yield. Note: This procedure can also be used, but the catalyst is prepared in situ by adding the appropriate amounts of SDPP and Pd(OAc)2.
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Tyrrell, Elizabeth; Whiteman, Leon; Williams, Neil [Synthesis, 2009, # 5, p. 829 - 835]
[2]Zhang, Jing; Ugrinov, Angel; Zhao, Pinjing [Angewandte Chemie - International Edition, 2013, vol. 52, # 26, p. 6681 - 6684][Angew. Chem., 2013, vol. 125, # 26, p. 6813 - 6816,4]
[3]Iranpoor, Nasser; Firouzabadi, Habib; Riazi, Asma [Journal of the Iranian Chemical Society, 2015, vol. 12, # 1, p. 155 - 165]
[4]Iranpoor, Nasser; Firouzabadi, Habib; Motevalli, Somayeh; Rajabi, Khashayar [Australian Journal of Chemistry, 2015, vol. 68, # 6, p. 926 - 930]
[5]Chang, Zhi-Xin; Li, Fu-Rong; Xia, Chengcai; Li, Fei; Li, Hong-Shuang [Advanced Synthesis and Catalysis, 2021, vol. 363, # 6, p. 1722 - 1726]

21
[ 103-64-0 ]
[ 5720-07-0 ]
[ 1694-19-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2H⁽¹⁺⁾Cl₄Pd^(2-)2H₃N; poly[N-isopropylacrylamide-co-diphenyl(4'-styryl)phosphine]; sodium carbonate In water at 100℃; for 24h;
91%	With sodium carbonate In water at 100℃; for 24h;

Reference： [1]Yamada, Yoichi M. A.; Takeda, Koji; Takahashi, Hideyo; Ikegami, Shiro [Journal of Organic Chemistry, 2003, vol. 68, # 20, p. 7733 - 7741]
[2]Yamada, Yoichi M. A.; Takeda, Koji; Takahashi, Hideyo; Ikegami, Shiro [Organic Letters, 2002, vol. 4, # 20, p. 3371 - 3374]

22
[ 201230-82-2 ]
[ 103-64-0 ]
[ 1888-75-1 ]
[ 60512-85-8 ]
(1E)-4-methyl-1-phenylpent-1-en-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 63% 2: 13%	Stage #1: isopropyllithium With indium(III) chloride In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: carbon monoxide; bromostyrene In tetrahydrofuran; hexane at 66℃; for 3h;

Reference： [1]Lee, Phil Ho; Lee, Sung Wook; Lee, Kooyeon [Organic Letters, 2003, vol. 5, # 7, p. 1103 - 1106]

23
[ 64187-51-5 ]
[ 103-64-0 ]
N-(4-methoxybenzylidene)styrylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium t-butanolate; DavePhos In toluene at 90℃; for 3h;

Reference： [1]Barluenga, Jose; Aznar, Fernando; Valdes, Carlos [Angewandte Chemie - International Edition, 2004, vol. 43, # 3, p. 343 - 345]

24
[ 103-64-0 ]
[ 96735-58-9 ]
N-(3-phenylallylidene)styrylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium t-butanolate; DavePhos In toluene at 90℃; for 3h;

Reference： [1]Barluenga, Jose; Aznar, Fernando; Valdes, Carlos [Angewandte Chemie - International Edition, 2004, vol. 43, # 3, p. 343 - 345]

25
[ 103-64-0 ]
[ 85654-07-5 ]
N-(4-chlorobenzylidene)styrylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium t-butanolate; DavePhos In toluene at 90℃; for 2h;

Reference： [1]Barluenga, Jose; Aznar, Fernando; Valdes, Carlos [Angewandte Chemie - International Edition, 2004, vol. 43, # 3, p. 343 - 345]

26
[ 103-64-0 ]
[ 100717-47-3 ]
2-methyl-2-styryl-5-(N-methyl-anilinomethylene)-cyclopentanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium t-butanolate In toluene at 20℃;

Reference： [1]Chieffi; Kamikawa; Ahman; Fox; Buchwald [Organic letters, 2001, vol. 3, # 12, p. 1897 - 1900]

27
[ 383-62-0 ]
[ 103-64-0 ]
2,2-difluoro-4-phenyl-but-3-enoic acid ethyl ester [ No CAS ]
(E)-ethyl 2,2-difluoro-4-phenylbut-3-enoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 8618 - 8621

28
[ 103-64-0 ]
[ 98-80-6 ]
[ 588-59-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; orotic acid; Cs₂CO₃ In acetone at 100℃; for 16h; Inert atmosphere;
58%	With Cs₂CO₃ In dimethyl sulfoxide at 135 - 140℃; for 24h;

Reference： [1]Chen, Shaohang; Cui, Chengsen; Duan, Peigao; Hollmann, Frank; Li, Huanhuan; Wever, Ron; Younes, Sabry H. H.; Zhang, Wuyuan [ACS Catalysis, 2022, vol. 12, # 8, p. 4554 - 4559]
[2]Li, Jin-Heng; Li, Ji-Lan; Xie, Ye-Xiang [Synthesis, 2007, # 7, p. 984 - 988]

29
[ 95-14-7 ]
[ 103-64-0 ]
2-(E)-β-styrylbenzotriazole [ No CAS ]
[ 111198-10-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 87% 2: 7%	With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h;

Reference： [1]Taillefer, Marc; Ouali, Armelle; Renard, Brice; Spindler, Jean-Francis [Chemistry - A European Journal, 2006, vol. 12, # 20, p. 5301 - 5313]

30
[ 201230-82-2 ]
[ 103-64-0 ]
[ 71-36-3 ]
[ 52392-64-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine at 60℃;
81%	With palladium diacetate; caesium carbonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In N,N-dimethyl-formamide at 80℃; Inert atmosphere;

Reference： [1]McNulty, James; Nair, Jerald J.; Robertson, Al [Organic Letters, 2007, vol. 9, # 22, p. 4575 - 4578]
[2]Location in patent: scheme or table McNulty, James; Nair, Jerald J.; Sliwinski, Marcin; Robertson, Al J. [Tetrahedron Letters, 2009, vol. 50, # 20, p. 2342 - 2346]

31
[ 201230-82-2 ]
[ 103-64-0 ]
[ 67-63-0 ]
[ 60512-85-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃;
64%	With palladium diacetate; caesium carbonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In N,N-dimethyl-formamide at 80℃; Inert atmosphere;
63%	With triethylamine at 60℃;

Reference： [1]Location in patent: scheme or table McNulty, James; Nair, Jerald J.; Capretta, Alfredo [Tetrahedron Letters, 2009, vol. 50, # 28, p. 4087 - 4091]
[2]Location in patent: scheme or table McNulty, James; Nair, Jerald J.; Sliwinski, Marcin; Robertson, Al J. [Tetrahedron Letters, 2009, vol. 50, # 20, p. 2342 - 2346]
[3]McNulty, James; Nair, Jerald J.; Robertson, Al [Organic Letters, 2007, vol. 9, # 22, p. 4575 - 4578]

32
[ 103-64-0 ]
[ 5097-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) Mg / 1.) THF, 2.) 5 min, THF 2: 7.4 percent / toluene / 24 h / Heating

Reference： [1]Katritzky, Alan R.; Beltrami, Hector; Sammes, Michael P. [Journal of Chemical Research, Miniprint, 1981, # 5, p. 1684 - 1696]

34
[ 354-38-1 ]
[ 103-64-0 ]
[ 14618-24-7 ]

Reference： [1]Patent: EP1178040,2002,A1 .Location in patent: Page 5-6
[2]Patent: EP1178040,2002,A1 .Location in patent: Page 11
[3]Patent: EP1178040,2002,A1 .Location in patent: Page 11
[4]Patent: EP1178040,2002,A1 .Location in patent: Page 11
[5]Patent: EP1178040,2002,A1 .Location in patent: Page 10
[6]Patent: EP1178040,2002,A1 .Location in patent: Page 10
[7]Patent: EP1178040,2002,A1 .Location in patent: Page 10
[8]Patent: EP1178040,2002,A1 .Location in patent: Page 10
[9]Patent: EP1178040,2002,A1 .Location in patent: Page 9
[10]Patent: EP1178040,2002,A1 .Location in patent: Page 8
[11]Patent: EP1178040,2002,A1 .Location in patent: Page 8, 9
[12]Patent: EP1178040,2002,A1 .Location in patent: Page 8
[13]Patent: EP1178040,2002,A1 .Location in patent: Page 8
[14]Patent: EP1178040,2002,A1 .Location in patent: Page column 8
[15]Patent: EP1178040,2002,A1 .Location in patent: Page 12
[16]Patent: EP1178040,2002,A1 .Location in patent: Page 8
[17]Patent: EP1178040,2002,A1 .Location in patent: Page 8

35
[ 748796-37-4 ]
[ 103-64-0 ]
[ 625390-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 48h; Heating in a sealed tube;	22.22a Example 22 Compound of formula I: A and B taken together with the carbon atom to which they are attached = C=CHCHCH-phenyl, X and Y taken together with the carbon atom to which they are attached = C=NAc, L = CH2CH3, W is N (CH3)2, Z = OC (benzyl and R2 = H. Step 22a. Compound of formula I : A and B taken together with the carbon atom to which they are attached are C=CHCH=CH-phenyl, X and Y taken together with the carbon atom to which they are attached are C=NAc, L = CH2CH3, W is N (CH3)2, Z = OH, and R2' = Ac.; To a solution of the compound of formula 1 : A and B taken together with the carbon atom to which they are attached are C=CH2, X and Y taken together with the carbon atom to which they are attached are C=NAc, L = CH2CH3, W is N (CH3) 2, Z = OH, and R2 = Ac (0.5 g, 0.7 mmol) in 8 ml anhydrous DMF, P-bromostyrene (0.15 ml, 1.2 mmol) and K2CO3 (200 mg, 1.5 mmol) were added at room temperature. The mixture was degassed briefly and a catalytic amount of dihydrogen dichlorobis (di-tert-butylphosphinito-KP) palladate (II) (POPd from Combiphos catalysts, Inc. ) was added. The reaction mixture was heated to 100°C in a sealed tube for 48 hours. Ethyl acetate (50 mL) was added and the solution was washed 3 times with aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Si02, acetone: hexanes/1 : 1) to provide the title compound. MS (ESI) m/z 813 (M+H) +
	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 100℃; for 48h;	35.35a To a solution of the compound of formula (1-5), wherein V = N-Ac, Rl l = H, and R2' = Ac (0.5 g, 0.7 mmol) in 8 ml anhydrous DMF, P-bromostyrene (0.15 ml, 1.2 mmol) and K2C03 (200 mg, 1.5 mmol) were added at room temperature. The mixture was degassed briefly and a catalytic amount of dihydrogen dichlorobis (di-tert-butylphosphinito- KP) palladate (II) (POPd from Combiphos catalysts, Inc. ) was added. The reaction mixture was heated to 100°C in a sealed tube for 48 hours. Ethyl acetate (50 mL) was added and the solution was washed 3 times with aqueous NaHC03. The organic layer was dried over anhydrous Na2S04. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (SiO2, acetone: hexanes/1 : 1) to provide the title compound. MS (ESI) m/z 813 (M+H) +

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2003/95466, 2003, A1 Location in patent: Page/Page column 74
[2]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2005/61525, 2005, A1 Location in patent: Page/Page column 115

36
[ 628703-03-7 ]
[ 103-64-0 ]
[ 625390-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 100℃; for 48h;	35.35a Compound of formula (1-5) : V is N-Ac, R_ is CH-CH-Ph, R9'= Ac To a solution of the compound of formula (1-5), wherein V = N-Ac, Rn = H, and R2' = Ac (0.5 g, 0.7 mmol) in 8 ml anhydrous DMF, p-bromostyrene (0.15 ml, 1.2 mmol) and K2CO3 (200 mg, 1.5 mmol) were added at room temperature. The mixture was degassed briefly and a catalytic amount of dihydrogen dichlorobis (di-tert-butylphosphinito- KP) palladate (II) (POPd from Combiphos catalysts, Inc. ) was added. The reaction mixture was heated to 100°C in a sealed tube for 48 hours. Ethyl acetate (50 mL) was added and the solution was washed 3 times with aqueous NaHC03. The organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Si02, acetone: hexanes/1 : 1) to provide the title compound. MS (ESI) m/z 813 (M+H) +

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2005/61526, 2005, A1 Location in patent: Page/Page column 121

37
C₃₇H₆₀N₂O₁₁ [ No CAS ]
[ 103-64-0 ]
[ 625390-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 48h; Heating in a sealed tube;	35.35a Example 35 Compound of formula 1 : A and B taken together with the carbon atom to which they are attached are C=CH-CH=CH-Ph, X and Y taken together with the carbon atom to which they are attached are C=N-Ac, L = CH_CH3, Z = H, and R'= H Step 35a: Compound of formula (1-5): V is N-Ac, R11 is CH-CH-Ph, R2' = Ac; To a solution of the compound of formula (1-5), wherein V = N-Ac, RI = H, and R2' = Ac (0.5 g, 0.7 mmol) in 8 ml anhydrous DMF, p-bromostyrene (0.15 ml, 1.2 mmol) and K2CO3 (200 mg, 1.5 mmol) were added at room temperature. The mixture was degassed briefly and a catalytic amount of dihydrogen dichlorobis (di-tert-butylphosphinito- XP) palladate (II) (POPd from Combiphos catalysts, Inc. ) was added. The reaction mixture was heated to 100°C in a sealed tube for 48 hours. Ethyl acetate (50 mL) was added and the solution was washed 3 times with aqueous NaHCO3. The organic layer was dried over anhydrous Na2S04. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (SiO2, acetone: hexanes/l: l) to provide the title compound. MS (ESI) m/z 813 (M+H) +

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2003/97659, 2003, A1 Location in patent: Page/Page column 121-122

38
C₃₅H₅₆N₂O₁₂ [ No CAS ]
[ 103-64-0 ]
C₄₄H₆₄N₂O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 100℃;	59 Example 59; Compound of Formula VII, Wherein R1 and R2 Taken Together with the Carbon Atom to which they are Attached are CCH[CHCHPh], R20H, and Rx=Ac; A mixture of compound from Example 16 (0.15 mmol), (2-bromo-vinyl)-benzene (1.6 eq.), potassium carbonate (2.6 eq.), and POPd (14 mol %) in acetonitrile (3 ml) was degassed, sealed and heated to 100° C. overnight. The mixture was then cooled and filtered through a pad of celite and the filtrate was evaporated to dryness. The residue was purified by column chromatography eluting with 1:3 (acetone/hexane) to give an off-white foam. MS (ESI): m/z 797.06 [M+H].

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - US2006/122128, 2006, A1 Location in patent: Page/Page column 49-50

39
[ 363-72-4 ]
[ 103-64-0 ]
(E)-1,2,3,4,5-pentafluoro-6-styrylbenzene [ No CAS ]
[ 80365-31-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With cesium hydroxide; phenylallylchloro-[1,3-bis(diisopropylphenyl)-2-imidazolidinylidene]palladium(II); [1,3-bis(tert-butyl)imidazol-2-ylidene]copper(I) chloride In toluene at 110℃; for 15h; Inert atmosphere; Glovebox; Overall yield = 98 %;
1: 77% 2: 12%	With potassium phosphate In N,N-dimethyl-formamide; xylene at 130℃; for 24h;

Reference： [1]Lesieur, Mathieu; Lazreg, Faïma; Cazin, Catherine S. J. [Chemical Communications, 2014, vol. 50, # 64, p. 8927 - 8929]
[2]Do, Hien-Quang; Daugulis, Olafs [Journal of the American Chemical Society, 2008, vol. 130, # 4, p. 1128 - 1129]

40
[ 103-64-0 ]
[ 107473-14-3 ]
[ 1271742-39-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With diisopropylamine at 20℃;

Reference： [1]Nieto-Oberhuber, Cristina; Perez-Galan, Patricia; Herrero-Gomez, Elena; Lauterbach, Thorsten; Rodriguez, Cristina; Lopez, Salome; Bour, Christophe; Rosellon, Antonio; Cardenas, Diego J.; Echavarren, Antonio M. [Journal of the American Chemical Society, 2008, vol. 130, # 1, p. 269 - 279]

41
[ 29032-56-2 ]
[ 103-64-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran N2-atmosphere; 43°C (18 h); filtering, washing (ether); elem. anal.;

Reference： [1]Huang, Chien-Chih; Duan, Jiun-Pey; Wu, Ming-Yuan; Liao, Fen-Ling; Wang, Sue-Lein; Cheng, Chien-Hong [Organometallics, 1998, vol. 17, # 4, p. 676 - 682]

42
[ 100-42-5 ]
[ 103-64-0 ]
[ 538-81-8 ]

Reference： [1]Synthesis,2008,p. 1142 - 1152

43
[ 5497-67-6 ]
[ 103-64-0 ]
[ 1039196-21-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium acetate In N,N-dimethyl-formamide at 110℃; for 20h;

Reference： [1]Lemhadri, Mhamed; Battace, Ahmed; Berthiol, Florian; Zair, Touriya; Doucet, Henri; Santelli, Maurice [Synthesis, 2008, # 7, p. 1142 - 1152]

44
[ 1968-40-7 ]
[ 103-64-0 ]
[ 1039196-18-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium acetate In N,N-dimethyl-formamide at 110℃; for 20h;

Reference： [1]Lemhadri, Mhamed; Battace, Ahmed; Berthiol, Florian; Zair, Touriya; Doucet, Henri; Santelli, Maurice [Synthesis, 2008, # 7, p. 1142 - 1152]

45
indium(III) benzenethiolate [ No CAS ]
[ 103-64-0 ]
[ 7214-53-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
95%	Stage #1: bromostyrene In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: indium(III) benzenethiolate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 2h;	4 Preparation of trans- β -styrenyl-phenylsulfide [formula 8] A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 niL) was stirred for 5 minutes under a nitrogen atmosphere. To this solution was added 1-bromostyrene (91.5 mg, 0.5 mmol) dissolved in 0.5 mL of DMF and then the reaction mixture was stirred for 10 minutes at room temperature. Li(SPh)3 (74mg, 0.167 mmol) in DMF ( 1 mL) and diisopropylethyl amine (65 mg, 0.5 mmol) were added to this reaction mixture.The reaction mixture was stirred for 2 hours at 100 degrees Celsius. The solution was cooled to room temperature and then 1 mL of hydrochloric acid (5 % of aqueous solution) was added to stop the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times) and sequentially washed with 10 mL of water, a saturated NaHCO3 (10 mL) solution and a saturated NaCl (20 mL) solution. The extracted organic compound was dried over anhydrous MgSO4 and then filtered. After evaporation of solvents, the crude product was purified by column chromatography to give /rø«s-beta-styrenyl-phenylsulfide (101 mg, 95 %) (formula 8). 1H-NMR (300 MHz, CDCl3) δ 7.60(m, 10H), 6.70(d, J=15.4Hz, IH), 6.62(d, J=15.4Hz, IH).

Reference： [1]Lee, Jae-Young; Phil, Ho Lee [Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7413 - 7416]
[2]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - WO2009/69888, 2009, A2 Location in patent: Page/Page column 10-11

46
[ 929-05-5 ]
[ 103-64-0 ]
C₁₄H₁₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; (3-(diphenylphosphaneyl)propyl)diphenylphosphine oxide In dimethyl sulfoxide at 115℃; for 5h; Inert atmosphere; regioselective reaction;

Reference： [1]Location in patent: experimental part McConville, Matthew; Saidi, Ourida; Blacker, John; Xiao, Jianliang [Journal of Organic Chemistry, 2009, vol. 74, # 7, p. 2692 - 2698]

47
[ 103-64-0 ]
[ 108-98-5 ]
[ 7214-56-4 ]
[ 7214-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: thiophenol With sodium t-butanolate In tetrahydrofuran at 23℃; for 0.166667h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #3: bromostyrene With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I); lithium iodide In tetrahydrofuran at 90℃; for 2h; Inert atmosphere;
81.818 % de	Stage #1: bromostyrene With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In toluene for 0.0333333h; Inert atmosphere; Stage #2: thiophenol With lithium hexamethyldisilazane In toluene at 110℃; Inert atmosphere; Overall yield = 91 %; Overall yield = 77 mg;
80 % de	With nickel(II) iodide; triisopropyl phosphite; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; Overall yield = 90 percent; Overall yield = 1.07 g; stereospecific reaction;	Ni-Catalyzed C-S Cross-Coupling Reaction; General Procedure 1 General procedure: Reactions were run in 2-dram vials and stir bars that were oven-dried overnight. The vial was charged with NiI2 (1.25 mol%), ligand P(OiPr)3 (5 mol%) under a flow of argon. DMF (1 mL) was added. Styryl bromide (0.42 mmol), DIPEA (2.5 equiv), and thiophenol (0.48 mmol) were added subsequently in that order. The vial was fitted with a Teflon cap and Teflon tape. The reaction was heated between 120 °C for 18 h. All NMR spectra were collected in CDCl3. Compounds were airstable at r.t. but were stored in the freezer for precaution. E/Z ratios were obtained via 1H NMR from the crude reaction mixture to avoid the possibility of artificial changes during the purification process. For the reaction run on a 5.6 mmol scale, all procedures were the same using a 9.5-dram vial and all reagents were scaled accordingly.

Reference： [1]Eichman, Chad C.; Stambuli, James P. [Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 4005 - 4008]
[2]Velasco, Noelia; Virumbrales, Cintia; Sanz, Roberto; Suárez-Pantiga, Samuel; Fernández-Rodríguez, Manuel A. [Organic Letters, 2018, vol. 20, # 10, p. 2848 - 2852]
[3]Larin, Egor M.; Lautens, Mark; Marchese, Austin D.; Mirabi, Bijan [Synthesis, 2020, vol. 52, # 2, p. 311 - 319]

48
[ 103-64-0 ]
[ 1906-57-6 ]
[ 4192-77-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane In 1-methyl-pyrrolidin-2-one at 150℃; for 10h; Inert atmosphere;

Reference： [1]Shang, Rui; Fu, Yao; Li, Jia-Bin; Zhang, Song-Lin; Guo, Qing-Xiang; Liu, Lei [Journal of the American Chemical Society, 2009, vol. 131, p. 5738 - 5739]

49
[ 103-64-0 ]
[ 169736-06-5 ]
[ 612503-58-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: (S)-1,4-dibenzyl-2-vinylpiperazine With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 20℃; for 16h; Stage #2: bromostyrene With sodium hydroxide; water In tetrahydrofuran for 24h; Heating / reflux;	192 Example 192; (S)-1, 4-Dibenzyl-2- .-piperazine; Combine 9-borabicyclo [3.3. 1] nonane (81.6 mL, 40.3 mmol, 0.5 M in THF) and (S)-1, 4-dibenzyl-2-vinyl-piperazine (2.0 g, 6.8 mmol) and stir at ambient temperature. After 16 hours, take half volume of it, add triphenylphosphine (143 mg, 0.55 mmol), tetrakis (triphenylphosphine) palladium (0) (78.5 mg, 0.068 mmol), and beta-bromostyrene (0.93 g, 5.08 mmol). Add 3N NaOH (2.8 mL, 8.8 mmol) slowly, gas evolution will occur. Heat to reflux. After 24 hours, cool to ambient temperature. Remove the solvent under reduced pressure, dilute with diethyl ether, wash with IN HC1, IN NaOH, H20 and brine, dry the organic layer over Na2S04, filter and concentrate under reduced pressure. Purification by flash chromatography on silica gel using 2N ammonia in methanol- methylene chloride (0.5%-3%) as the eluent, collect compound and pass through 10 g SCX column, using MeOH, 0.2 N NH3 in MeOH as eluent to give the title compound (750 mg, 56%): mass spectrum (electrospray): m/z = 397.3 (M+1) ; 1H NMR (300 MHz, CDC13) : 87. 35-7.16 (m, 15H), 6.36-6. 12 (m, 2H), 4.01 (d, 1H, J= 13.2), 3.56-3. 43 (m, 2H), 3.25 (d, 1 H, J = 13.4 Hz), 2.75-2. 68 (m, 2H), 2.56-2. 48 (m, 2H), 2.29-2. 13 (m, 5H), 1.82-1. 76 (m, 2H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2003/82877, 2003, A1 Location in patent: Page/Page column 93

50
[ 23012-14-8 ]
[ 103-64-0 ]
[ 1134024-11-5 ]
[ 132629-37-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 647 - 650

51
[ 103-64-0 ]
[ 637-44-5 ]
[ 13343-79-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	17 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.
92%	Stage #1: bromostyrene; phenylpropyolic acid With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium chloride; silver(l) oxide In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; Stage #2:

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]
[2]Location in patent: scheme or table Kim, Hyunseok; Lee, Phil Ho [Advanced Synthesis and Catalysis, 2009, vol. 351, # 17, p. 2827 - 2832]

52
[ 103-64-0 ]
[ 1626-24-0 ]
[ 103-30-0 ]
[ 82598-07-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 816 - 819

53
[ 103-64-0 ]
[ 1074-29-9 ]
[ 103-30-0 ]
[ 886-65-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 28% 2: 9%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 100℃; for 12h; Inert atmosphere;

Reference： [1]Zhang, Zun-Ting; Pitteloud, Jean-Philippe; Cabrera, Laura; Liang, Yong; Toribio, Myrdich; Wnuk, Stanislaw F. [Organic Letters, 2010, vol. 12, # 4, p. 816 - 819]

54
[ 103-64-0 ]
[ 1552-94-9 ]
[ 17329-15-6 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 592 - 595

55
[ 95-14-7 ]
[ 103-64-0 ]
[ 1380345-33-4 ]
[ 111198-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2,3-Benzotriazole With copper(l) iodide; 2-(2'-pyridyl)benzimidazole; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: bromostyrene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;

Reference： [1]Kabir, M. Shahjahan; Lorenz, Michael; Namjoshi, Ojas A.; Cook, James M. [Organic Letters, 2010, vol. 12, # 3, p. 464 - 467]

56
[ 1158098-73-7 ]
[ 103-64-0 ]
[ 1211284-17-1 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1116 - 1119

57
[ 6262-87-9 ]
[ 103-64-0 ]
C₁₇H₁₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium phosphate; copper(l) iodide; cis-1,2-cyclohexane In N,N-dimethyl-formamide at 80℃; for 15h;

Reference： [1]Location in patent: scheme or table Kabir, M. Shahjahan; Lorenz, Michael; Van Linn, Michael L.; Namjoshi, Ojas A.; Ara, Shamim; Cook, James M. [Journal of Organic Chemistry, 2010, vol. 75, # 11, p. 3626 - 3643]

58
[ 621-82-9 ]
[ 103-64-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide In dichloromethane at 20℃; for 4h;
92%	With N-Bromosuccinimide; manganese (II) acetate tetrahydrate In water; acetonitrile at 20℃;
75%	With N,N-dimethyl-formamide; potassium bromide; trichlorophosphate In acetonitrile at 20℃; Sonication;	Ultrasonically Assisted Vilsmeier-Haack Synthesis ofb-Bromostyrenes (Sonication) General procedure: To a centimolar cinnamic acid, 0.015 mol of Vilsmeier-Haackreagent and KBr and solvent (Me CN) were added in a cleanin a round bottom flask and clamped in a sonicator at roomtemperature. After completion of the reaction, as ascertainedby TLC, the reaction mixture is treated with sodium thiosulfate solution, followed by the addition of ethyl acetate. Theseparation and purification procedure is by and large similarto the above procedure.

	Stage #1: Cinnamic acid With lithium acetate In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In water; acetonitrile at 20℃;	3.3. General procedure for preparation of vinyl halides¹¹ General procedure: β-Unsaturated carboxylic acid (1.48 g, 10 mmol) was added to a solution of LiOAc (0.07 g, 1 mmol) in MeCN/H2O (97:3 v/v, 30 mL). After the mixture was stirred for 5 min at room temperature, 1-iodopyrrolidine-2,5-dione (2.25 g, 10 mmol) was added. Usual workup by flash column chromatography on silica gel to afford the 1-((E)-2-bromovinyl)benzene 2a (1.36 g, 85%).
	Stage #1: Cinnamic acid With lithium acetate In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In water; acetonitrile	Synthesis of substituted beta bromostyrenes² General procedure: α,β-Unsaturated cinnamic acid (300mg, 2mmol) was added to a solution of lithium acetate (13mg, 0.2mmol) in4.5mL of acetonitrile:water (97:3v/v). After the mixture was stirred for 5min at RT, N-bromosuccinimide (370mg,2.1mmol) was added as a solid portion wise. Reaction progress was monitored by TLC. Usual workup followed bysilicagel column chromatography afforded the pure haloalkene.Thestereoselectivity (E:Z) was measured by GC-MS.
	With N-Bromosuccinimide; manganese (II) acetate tetrahydrate In water; acetonitrile at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Fursule, Ravindra Abhykumar; Patil, Pravin Onkar; Shewale, Bharti Devaji; Kosalge, Satish Bhaskar; Deshmukh, Prashant Krishnarao; Patil, Dilip Ashok [Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 11, p. 1243 - 1245]
[2]Cai, Guilong; Zhou, Zhibing; Wu, Wenchao; Yao, Bo; Zhang, Shaowen; Li, Xiaofang [Organic and Biomolecular Chemistry, 2016, vol. 14, # 37, p. 8702 - 8706]
[3]Kumar, M. Satish; Rajanna; Venkanna; Venkateswarlu; Sudhakar Chary [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2016, vol. 46, # 5, p. 642 - 646]
[4]Location in patent: experimental part Xu, Run-Sheng; Yue, Lei; Pan, Yuan-Jiang [Tetrahedron, 2012, vol. 68, # 25, p. 5046 - 5052]
[5]Mohan, Balaji; Hwang, Sori; Woo, Hyunje; Park, Kang Hyun [Tetrahedron, 2014, vol. 70, # 17, p. 2699 - 2702]
[6]Li, Huan; Zhang, Zhikun; Shangguan, Xianghang; Huang, Shan; Chen, Jun; Zhang, Yan; Wang, Jianbo [Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11921 - 11925][Angew. Chem., 2014, vol. 126, # 44, p. 12115 - 12119,5]

59
[ 103-64-0 ]
[ 536-74-3 ]
[ 13343-79-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	1 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.
98%	With iodo(4,5-bis(diphenylphosphano)-9,9-dimethylxanthene)copper(I); caesium carbonate In 1,4-dioxane at 135℃; for 24h; Inert atmosphere;
82%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 25℃; for 12h;

70%	With tetrabutylammomium bromide; potassium acetate at 100℃; for 15h; Inert atmosphere;
67%	With copper(I) oxide; caesium carbonate In N,N-dimethyl-formamide at 135℃; for 24h; Inert atmosphere;	General procedure for Table 4: General procedure: A sealable vial equipped with a magnetic stir bar was charged with Cs2CO3 (325 mg, 1.0 mmol), Cu2O (3.5mg, 0.025 mmol) under a nitrogen atmosphere. The aperture of the vial was then covered with a rubber septum. Under a nitrogen atmosphere, alkyne (1, 0.75 mmol), vinyl halide (6, 0.5 mmol) and DMF (0.5 mL) were added by syringe. The septum was then replaced by a screw cap containing a Teflon-coated septum,and the reaction vessel was placed at 135 °C. After stirring at this temperature for 12-24 h, the heterogeneous mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). Theresulting solution was filtered through a pad of silica gel then washed with ethyl acetate (20 mL) and concentrated to give the crude material which was then purified by column chromatography on silica gel to yield enynes 7.
52%	With potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 135℃; for 24h; Inert atmosphere;	4.4.1. (E)-1,4-Diphenylbut-1-en-3-yne (7a, >99%E) According to the typical procedure, the reaction of 1a (103 mg,1.01 mmol) with HBr (30 wt% in AcOH, 325 mg, 1.21 mmol) was carried out in toluene (2 mL) for 30 min. The crude product 2a was subjected to the Cu-mediated coupling with 1a as follows [14]. Under an argon atmosphere, a solution of 2a in DMSO (5 mL) and 1a (128 mg, 1.25 mmol) were added to a mixture of CuI (191 mg,1.00 mmol) and K3PO4 (428 mg, 2.02 mmol). The mixture was heated to 135 °C and stirred for 24 h. The resultant mixture was cooled to room temperature and diluted with H2O (10 mL). The mixture was extracted with hexane (15 mL) and EtOAc (15 mL). The combined organic layers were washed by brine (10 mL) and dried over Na2SO4 and evaporated under reduced pressure. Purificationof the residual oil by silica gel column chromatography (hexane) gave 7a as white solid (108 mg, 0.529 mmol, 52%, >99%E). 1H NMR (400 MHz, CDCl3) d 7.50e7.43 (m, 4H), 7.37e7.30 (m, 6H), 7.05 (d,J 16.4 Hz, 1H), 6.40 (d, J 16.4 Hz, 1H); 13C NMR (101 MHz, CDCl3) d 141.3, 136.3, 131.5, 128.7, 128.6, 128.3, 128.2, 126.3, 123.4, 108.1,91.7, 88.9. These data are in accordance with the literature values [37].
40%	With CuI(xantphos); caesium carbonate In N,N-dimethyl-formamide at 135℃; for 1h; Inert atmosphere; Microwave irradiation;

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]
[2]Lin, Yun-Yung; Wang, Yu-Jen; Cheng, Jun-Hao; Lee, Chin-Fa [Synlett, 2012, vol. 23, # 6, p. 930 - 934]
[3]Li, Jincan; Li, Wanfang; Yu, Shun; Zhao, Yu [Angewandte Chemie - International Edition, 2020, vol. 59, # 34, p. 14404 - 14408][Angew. Chem., 2020, vol. 132, # 34, p. 14510 - 14514,5]
[4]Location in patent: experimental part Firouzabadi, Habib; Iranpoor, Nasser; Ghaderi, Arash [Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 865 - 871]
[5]Tsai, Wan-Ting; Lin, Yun-Yung; Chen, Yi-An; Lee, Chin-Fa [Synlett, 2014, vol. 25, # 3, p. 443 - 447]
[6]Kumaki, Wataru; Kinoshita, Hidenori; Miura, Katsukiyo [Tetrahedron, 2022, vol. 110]
[7]Tsai, Wen-Ting; Lin, Yun-Yung; Wang, Yu-Jen; Lee, Chin-Fa [Synthesis, 2012, vol. 44, # 10, p. 1507 - 1510]

60
[ 103-64-0 ]
[ 794-50-3 ]
4-phenyl-1,3-bis-(2,4,6-trimethylphenyl)-1H-1,2,3-triazolium hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: bromostyrene; 1,3-bis-(2,4,6-trimethylphenyl)triaz-1-ene With potassium hexafluorophosphate; tert-butylhypochlorite In dichloromethane at -78 - 20℃; Darkness; Stage #2: In acetone at 20℃; for 1h;	9; 35 Example 35; [0145] 1 ,3-Bis(2,4,6-trimethylylphenyl)-4-phenyl- 1H- 1 ,2,3-triazoliumhexafiuorophosphate (lOba), alternate preparation. To a stirred suspension of triazene 8b (5.63 g, 20 mmol) and anhydrous potassium hexafiuorophosphate (3.68 g, 10 mmol) and β- bromostyrene 11a (mixture of isomers, 5.13 mL, 40 mmol) in dry dichloromethane (100 mL) in the dark at -78°C is added tert-butyl hypochlorite (3.33 mL, 30 mmol), upon which the mixture instantly darkens. The mixture is stirred overnight as it is slowly allowed to warm to room temperature. The contents are then filtered, and the solid residue is washed with dichloromethane. The filtrate is collected, and volatiles are evaporated under reduced pressure. Diethyl ether is then added, and the mixture is vigorously triturated for ca. Ihour, with occasional scratching of the glass surfaces to ensure efficient mixing. Filtration and washing with copious quantities of diethyl ether afford, after drying under vacuum, triazolium salt lOba as an off-white solid (10.21 g, 97%). Analytical samples were obtained after recrystallization by vapor diffusion of diethyl ether in an acetonitrile solution of lOba. Characterization data are identical as for lOba prepared by the first method.

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2011/139704, 2011, A2 Location in patent: Page/Page column 32-34; 56

61
[ 103-64-0 ]
[ 1294447-76-9 ]
1,3-bis(2,6-difluorophenyl)-4-phenyl-1H-1,2,3-triazolium hexafluorophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hexafluorophosphate; tert-butylhypochlorite In dichloromethane at -78 - 20℃; Darkness;	9; 42 Example 42; [0153] l,3-Bis(2,6-difluorophenyl)-4-phenyl-lH-l,2,3-triazolium hexafluorophosphate (lOda), alternate preparation. To a stirred suspension of triazene 8d (808 mg, 3 mmol) and anhydrous potassium hexafluorophosphate (750 mg, 4 mmol) and β-bromostyrene 11a (mixture of isomers, 770 μ, 6 mmol) in dry dichloromethane (20 mL) in the dark at -78°C is added tert-butyl hypochlorite (500 μ, 4.4 mmol), upon which the mixture instantly darkens. The mixture is stirred overnight as it is slowly allowed to warm to room temperature. The contents are then filtered, and the solid residue is washed with dichloromethane. The filtrate is collected, and volatiles are evaporated under reduced pressure. Diethyl ether is then added, and the mixture is vigorously triturated for ca. Ihour, with occasional scratching of the glass surfaces to ensure efficient mixing. Filtration and washing with copious quantities of diethyl ether afford, after drying under vacuum, triazolium salt lOda as a white solid (1.55 g, 100%). Analytical samples were obtained after recrystallization by vapor diffusion of diethyl ether in an acetonitrile solution of lOda. Characterization data are identical as for lOda prepared by the first method.

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2011/139704, 2011, A2 Location in patent: Page/Page column 34-35; 61

62
[ 103-64-0 ]
[ 1864-94-4 ]
[ 2757-04-2 ]
[ 330983-74-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3100 - 3103

63
[ 93-52-7 ]
[ 103-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In ethanol at 80℃; for 0.166667h;	Synthesis of acetylenes from vicinal dibromides General procedure: A mixture of vicinal dibromide (5 mmol), anhydrous K3PO4 (5 mmol), PEG-900 (1.25 mmol), and EtOH (10 mL) was stirred at 80 °C. The progress of the reaction was monitored by analysis of the samples using TLC and gas chromatography. When the vicinal dibromide had been completely converted into the monobromo product, a second portion of K3PO4 (5 mmol) was added.Following completion of the reaction the mixture was filtered and the filtrate was diluted with CH2Cl and washed several times with H2O. The organic phase was dried over MgSO4 and evaporated under vacuum to afford a mixture of product and the monobromo derivative. The acetylene was separated by vacuum distillation. The identity and purity of the products were confirmed by GC-MS and 1H NMR spectroscopy.

Reference： [1]Location in patent: experimental part Shenawi-Khalil, Sanaa; Sonavane, Sachin U.; Sasson, Yoel [Tetrahedron Letters, 2012, vol. 53, # 18, p. 2295 - 2297]

64
[ 103-64-0 ]
[ 837-18-3 ]
5-(benzenesulfonyl-benzyl-amino)-4-phenyl-penta-2,4-dienoic acid benzyl ester [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3304 - 3307

65
[ 103-64-0 ]
[ 837-18-3 ]
N-benzyl-N-styryl-benzenesulfonamide [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3304 - 3307

66
[ 103-64-0 ]
[ 24388-23-6 ]
[ 588-59-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	With palladium diacetate; caesium carbonate In methanol; toluene at 60℃; for 7h;	General procedure for Suzuki coupling: General procedure: Preparation of biphenyl-4-carbonitrile (38): Pd(OAc)2 (2.3 mg, 1 mmol %), 4-bromo-benzonitrile (37) (182 mg, 1.0 mmol), 4,4,6-trimethyl-2-phenyl-[1,3,2] dioxaborinane (26) (224.4 mg, 1.1 mmol), Cs2CO3 (650 mg, 2 mmol), toluene (4 mL)-methanol (1 mL) were mixed together in a small reaction tube and the mixture was heated at 60 °C. The reaction progress was followed by TLC (15% ethyl acetate:hexanes). After the starting materials were consumed the mixture was cooled and filtered through celite followed by washing with toluene. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (15% ethyl acetate:hexanes) to obtain the title compound in 95% yield. 1H NMR (400 MHz, CDCl3): δ 7.74-7.67 (m, 4H), 7.62-7.58 (m, 2H), 7.53-7.41 (m, 3H). 13C NMR (100.6 MHz, CDCl3): δ 145.9, 139.4, 133.7, 132.9, 132.8, 129.4, 128.9, 128.0, 127.5, 119.2, 111.1

Reference： [1]Location in patent: experimental part Myslinska, Malgorzata; Heise, Glenn L.; Walsh, Dana J. [Tetrahedron Letters, 2012, vol. 53, # 24, p. 2937 - 2941]

67
[ 103-64-0 ]
C₇H₅F₃OS [ No CAS ]
5-(trifluoromethyl)-2-(styrylthio)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; regioselective reaction;	3.4. General procedure for synthesis of 2-(styrylthio)phenols derivatives 3a-3w, 5a-5n, 7a-7f General procedure: A mixture of thiophenols (0.5 mmol), 1-((E)-2-iodovinyl)benzenes (0.6 mmol), CuI (19 mg, 20 mol %), L5 (19 mg, 20 mol %), and Cs2CO3 (326 mg, 2 equiv) in DMSO (3 mL) was stirred in N2 at 100 °C for 24 h., The mixture was quenched with saturated salt water (10 mL) after the reaction completion. The solution was extracted with ethyl acetate (3×10 mL). The organic layers were combined and dried by sodium sulfate. The product 2-(styrylthio)phenols was obtained by flash column chromatography on silica gel.

Reference： [1]Location in patent: experimental part Xu, Run-Sheng; Yue, Lei; Pan, Yuan-Jiang [Tetrahedron, 2012, vol. 68, # 25, p. 5046 - 5052]

68
[ 103-64-0 ]
C₆H₄Cl₂OS [ No CAS ]
4,5-dichloro-2-(styrylthio)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; regioselective reaction;	3.4. General procedure for synthesis of 2-(styrylthio)phenols derivatives 3a-3w, 5a-5n, 7a-7f General procedure: A mixture of thiophenols (0.5 mmol), 1-((E)-2-iodovinyl)benzenes (0.6 mmol), CuI (19 mg, 20 mol %), L5 (19 mg, 20 mol %), and Cs2CO3 (326 mg, 2 equiv) in DMSO (3 mL) was stirred in N2 at 100 °C for 24 h., The mixture was quenched with saturated salt water (10 mL) after the reaction completion. The solution was extracted with ethyl acetate (3×10 mL). The organic layers were combined and dried by sodium sulfate. The product 2-(styrylthio)phenols was obtained by flash column chromatography on silica gel.

Reference： [1]Location in patent: experimental part Xu, Run-Sheng; Yue, Lei; Pan, Yuan-Jiang [Tetrahedron, 2012, vol. 68, # 25, p. 5046 - 5052]

69
[ 103-64-0 ]
[ 113269-55-9 ]
5-bromo-2-(styrylthio)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; regioselective reaction;	3.4. General procedure for synthesis of 2-(styrylthio)phenols derivatives 3a-3w, 5a-5n, 7a-7f General procedure: A mixture of thiophenols (0.5 mmol), 1-((E)-2-iodovinyl)benzenes (0.6 mmol), CuI (19 mg, 20 mol %), L5 (19 mg, 20 mol %), and Cs2CO3 (326 mg, 2 equiv) in DMSO (3 mL) was stirred in N2 at 100 °C for 24 h., The mixture was quenched with saturated salt water (10 mL) after the reaction completion. The solution was extracted with ethyl acetate (3×10 mL). The organic layers were combined and dried by sodium sulfate. The product 2-(styrylthio)phenols was obtained by flash column chromatography on silica gel.

Reference： [1]Location in patent: experimental part Xu, Run-Sheng; Yue, Lei; Pan, Yuan-Jiang [Tetrahedron, 2012, vol. 68, # 25, p. 5046 - 5052]

70
[ 103-64-0 ]
[ 4525-65-9 ]
[ 1402012-77-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 5370 - 5373,4

71
[ 103-64-0 ]
[ 1885-38-7 ]

Yield	Reaction Conditions	Operation in experiment
83%		General procedure: beta-Bromostyrene (1.10 g, 6.0 mmol) in THF (7.5 mL) was added toa flask containing Mg turnings (0.17 g, 6.9 mmol) at room temperature. After being stirred for 1.5 h, N-formylpiperidine (0.34 g,3.0 mmol) in THF (2 mL) was added to the reaction mixture at 0C and the obtained mixture was stirred for 1 h at room temperature.Then, acetic anhydride (0.6 mL, 6.0 mmol) was added to the reactionmixture at 0 C and the mixturewas stirred for 0.5 h at roomtemperature. Then, aq NH3 (6 mL, 28-30%) and I2 (1.53 g, 6.0 mmol) were added to the reaction mixture at 0C and the obtainedmixture was stirred for 0.5 h at room temperature. Then, the reaction mixture was quenched with satd aq Na2SO3 and was extracted with CHCl3 (3*20 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue waspurified by short column chromatography on silica gel (eluent:hexane/ethyl acetate=9:1, v/v) to provide pure cinnamonitrile (0.32 g) in 83% yield.

Reference： [1]Tetrahedron,2013,vol. 69,p. 1462 - 1469

72
[ 103-64-0 ]
[ 1315335-86-4 ]
1-allyl-5-methoxy-3-oxo-2-(3-phenylallyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In acetone at 130℃; for 1.5h; Microwave irradiation;	6 4.2.6. 1-Allyl-5-methoxy-3-oxo-2-(3-phenyl-allyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (7) General procedure: Oil 161 mg (yield 96%). IR (ATR) vmax=1737, 1696 cm-1; Rf 0.39 (n-Hexane/EtOAc, 4:1); 1H NMR (300 MHz, CDCl3) δ 7.24-7.08 (m, 5H), 7.02 (d, J=2.3 Hz, 1H), 6.78 (d, J=8.9 Hz, 1H), 6.49 (d, J=15.7 Hz, 1H), 5.99-5.78 (m, 2H), 5.36-5.18 (m, 2H), 4.23-4.10 (m, 2H), 4.09-3.84 (m, 2H), 3.75 (s, 3H), 3.18-3.02 (m, 2H), 1.22 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3); δ 195.3, 167.5, 157.8, 152.6, 137.0, 134.5, 133.8, 128.4 (2CH), 128.3, 127.3, 126.1 (2CH), 122.5, 119.4, 117.2, 111.0, 105.2, 78.3, 62.1, 55.7, 47.7, 36.4, 14.1; HRMS (C24H25NO4): calcd, 391.1784 found, 391.1797. Elemental analysis for C24H25NO4. Calcd: C, 73.64%, H, 6.44%, N, 3.58%. Found: C, 72.96%, H, 6.47%, N, 4.06%.

Reference： [1]Pagire, Haushabhau S.; Chun, Hang-Suk; Bae, Myung Ae; Ahn, Jin Hee [Tetrahedron, 2013, vol. 69, # 14, p. 3039 - 3044]

73
[ 103-64-0 ]
[ 4079-51-0 ]
4-bromo-2-(2-hydroxy-4-phenylbut-3-yn-2-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 0℃; for 1h;

Reference： [1]Schevenels, Florian; Tinant, Bernard; Declercq, Jean-Paul; Markó, István E. [Chemistry - A European Journal, 2013, vol. 19, # 13, p. 4335 - 4343]

74
[ 103-64-0 ]
[ 766-97-2 ]
(E)-1-methyl-4-(4-phenylbut-3-en-1-yn-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	2 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

75
[ 103-64-0 ]
[ 40307-11-7 ]
[ 1201221-03-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	3 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

76
[ 103-64-0 ]
[ 79887-10-8 ]
[ 1448055-65-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	4 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

77
[ 103-64-0 ]
[ 768-60-5 ]
[ 116156-19-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	5 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

78
[ 103-64-0 ]
[ 79887-14-2 ]
(E)-1-phenyl-4-(4-ethoxyphenyl)but-1-en-3-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine; In water; dimethyl sulfoxide; at 100℃; for 24h;Inert atmosphere; Green chemistry;	General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 muL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Tetrahedron,2013,vol. 69,p. 6969 - 6974

79
[ 766-98-3 ]
[ 103-64-0 ]
(E)-1-fluoro-4-(4-phenylbut-3-en-1-yn-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	7 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

80
[ 873-73-4 ]
[ 103-64-0 ]
(E)-1-phenyl-4-(4-chlorophenyl)but-1-en-3-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	8 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

81
[ 2227-57-8 ]
[ 103-64-0 ]
[ 116156-19-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	17 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

82
[ 2227-58-9 ]
[ 103-64-0 ]
(E)-1-methyl-4-(4-phenylbut-3-en-1-yn-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	17 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

83
[ 3240-10-6 ]
[ 103-64-0 ]
(E)-1-phenyl-4-(4-chlorophenyl)but-1-en-3-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Green chemistry;	17 General procedure for low-loading copper-catalyzed coupling of vinyl halide and alkyne in the presence of PPh₃ as the ligand performed in water General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 μL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100°C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Tetrahedron, 2013, vol. 69, # 34, p. 6969 - 6974]

84
[ 60007-39-8 ]
[ 103-64-0 ]
[ 95452-52-1 ]
[ 95452-51-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 11%	With triethylamine tris(hydrogen fluoride) at 23℃; for 63h; Inert atmosphere; Sealed tube;
1: 85% 2: 11%	With 1,3-bis(trifluoromethyl)benzene at 50℃; for 32h;	23 EXAMPLE 23 EXAMPLE 23 To β-bromostyrene (cis/trans = 1:8; purity 96%; 17 μL; 0.125 mmol) were added a CuC2F5 solution obtained as in Example 18 (0.425 M; 0.44 mL; 1.5 equiv) and 1,3-bis(trifluoromethyl)benzene (internal standard; 9.7 μL). After 63 hours at room temperature, GC-MS and quantitative 19F NMR analysis indicated the formation of (3,3,4,4,4-pentafluorobut-1-en-1-yl)benzene as a mixture of E (85%) and Z (11%) isomers at >99% conversion of β-bromostyrene.
84.615 % de	With air In N,N-dimethyl-formamide at 90℃; for 60h; Inert atmosphere; Overall yield = 74 %; Overall yield = 33.1 mg;

1: 85 %Chromat. 2: 11 %Chromat.

In N,N-dimethyl-formamide at 20℃; for 63h;

23 To β-bromostyrene (cis/trans = 1:8; purity 96%; 17 μL; 0.125 mmol) were added a CuC2F5 solution obtained as in Example 18(0.425 M; 0.44 mL; 1.5 equiv) and 1,3-bis(trifluoromethyl)benzene (internal standard; 9.7 pL). After 63 hours at room temperature, GC-MS and quantitative 19F NMR analysis indicated the formation of (3,3,4,4,4-pentafluorobut-1-en-1-yl)benzene as a mixture of E (85%) and Z (11%) isomers at >99% conversion of β-bromostyrene.

Reference： [1]Lishchynskyi, Anton; Grushin, Vladimir V. [Journal of the American Chemical Society, 2013, vol. 135, # 34, p. 12584 - 12587]
[2]Current Patent Assignee: GOVERNMENT OF SPAIN - EP2835374, 2015, A1 Location in patent: Paragraph 0211
[3]Serizawa, Hiroki; Aikawa, Kohsuke; Mikami, Koichi [Organic Letters, 2014, vol. 16, # 13, p. 3456 - 3459]
[4]Current Patent Assignee: GOVERNMENT OF SPAIN - WO2015/18855, 2015, A1 Location in patent: Page/Page column 43

85
[ 103-64-0 ]
[ 100-59-4 ]
[ 103-29-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N,N′-Bis(2-pyridylmethylidene)-1,2-trans-(R,R + S,S)-cyclohexanediamine; hydrogen; iron(II) chloride In tetrahydrofuran at -20 - 20℃; for 18h;

Reference： [1]Frank, Dominik J.; Guiet, Lea; Kaeslin, Alexander; Murphy, Elliot; Thomas, Stephen P. [RSC Advances, 2013, vol. 3, # 48, p. 25698 - 25701]

86
[ 103-64-0 ]
[ 1408285-51-7 ]
(E)-4,4,5,5-tetramethyl-2-(5-styrylthiophen-2-yl)-1,3,2-dioxaborolane [ No CAS ]
[ 239075-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 60℃; for 16h;

Reference： [1]He, Lu-Ying; Schulz-Senft, Mathias; Thiedemann, Birk; Linshoeft, Julian; Gates, Paul J.; Staubitz, Anne [European Journal of Organic Chemistry, 2015, vol. 2015, # 11, p. 2498 - 2502]

87
[ 103-64-0 ]
[ 1408285-51-7 ]
(E)-4,4,5,5-tetramethyl-2-(5-styrylthiophen-2-yl)-1,3,2-dioxaborolane [ No CAS ]
(Z)-4,4,5,5-tetramethyl-2-(5-styrylthiophen-2-yl)-1,3,2-dioxaborolane [ No CAS ]
[ 239075-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene at 60℃; for 17h;

Reference： [1]He, Lu-Ying; Schulz-Senft, Mathias; Thiedemann, Birk; Linshoeft, Julian; Gates, Paul J.; Staubitz, Anne [European Journal of Organic Chemistry, 2015, vol. 2015, # 11, p. 2498 - 2502]

88
[ 103-64-0 ]
[ 1408285-51-7 ]
(E)-4,4,5,5-tetramethyl-2-(5-styrylthiophen-2-yl)-1,3,2-dioxaborolane [ No CAS ]
(Z)-4,4,5,5-tetramethyl-2-(5-styrylthiophen-2-yl)-1,3,2-dioxaborolane [ No CAS ]
[ 82598-07-0 ]
[ 239075-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane; toluene at 65℃; for 26h;

Reference： [1]He, Lu-Ying; Schulz-Senft, Mathias; Thiedemann, Birk; Linshoeft, Julian; Gates, Paul J.; Staubitz, Anne [European Journal of Organic Chemistry, 2015, vol. 2015, # 11, p. 2498 - 2502]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	103-64-0	MDL No. :	MFCD00000185
Formula :	C₈H₇Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YMOONIIMQBGTDU-VOTSOKGWSA-N
M.W :	183.05	Pubchem ID :	5314126
Synonyms :

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.4
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.19 cm/s

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	3.13
Log Po/w (WLOGP) :	2.94
Log Po/w (MLOGP) :	3.32
Log Po/w (SILICOS-IT) :	3.01
Consensus Log Po/w :	2.94

[ CAS No. 103-64-0 ] {[proInfo.proName]}

Quality Control of [ 103-64-0 ]

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Physicochemical Properties

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Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 103-64-0 ]

Application In Synthesis of [ 103-64-0 ]

[ 103-64-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 103-64-0 ]

Aryls

Alkenes

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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

Log S (ESOL) :	-3.37
Solubility :	0.0773 mg/ml ; 0.000423 mol/l
Class :	Soluble
Log S (Ali) :	-2.8
Solubility :	0.291 mg/ml ; 0.00159 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.34
Solubility :	0.0839 mg/ml ; 0.000458 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
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P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
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P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 103-64-0 ] {[proInfo.proName]}

Quality Control of [ 103-64-0 ]

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[ 103-64-0 ] Synthesis Path-Downstream 1~88

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Aryls

Alkenes

Bromides

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[ 103-64-0 ]