873-31-4 (2-氯苯乙炔,1-Chloro-2-ethynylbenzene)

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Methanol ; 2 h, rt
1.2 Solvents: Water ; rt

参考文献：

The synthesis of [1,2,3]-triazole-based bent core liquid crystals via microwave-mediated 'Click Reaction' and their mesomorphic behaviour

Wang, Kunlun; et al, Liquid Crystals, 2019, 46(2), 257-271

合成路线：1 步

105273-33-4

_86%

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Methanol ; 3 h, rt

参考文献：

Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization

Li, Jing; et al, Organic Letters, 2015, 17(10), 2522-2525

合成路线：1 步

105273-33-4

_78%

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Methanol

参考文献：

An efficient and general procedure for the cross-coupling of trimethylsilylacetylene and vinylic, aromatic or heteroaromatic bromides

Brandsma, L.; et al, Synthetic Communications, 1990, 20(12), 1889-92

合成路线：1 步

119450-02-1

_92%

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ; 12 h, 115 °C

参考文献：

Convenient synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids using a K2CO3/DMSO system

Cheng, Xuezhi; et al, Chinese Journal of Chemistry, 2011, 29(11), 2350-2354

合成路线：1 步

119450-02-1

_90%

反应条件：

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ; 1.0 min
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ; 1.0 min

参考文献：

Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction

Kuang, Chunxiang; et al, Tetrahedron, 2005, 61(16), 4043-4052

合成路线：1 步

119450-02-1

_90%

反应条件：

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ; 1 min; rt
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ; 1 min
1.3 Solvents: Diethyl ether , Water

参考文献：

A one-pot synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids under microwave irradiation

Kuang, Chunxiang; et al, Chemistry Letters, 2005, 34(1), 28-29

合成路线：1 步

401514-40-7

_92%

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride , Triphenylphosphine Solvents: Tetrahydrofuran , Water ; 3 h, 80 °C

参考文献：

An Efficient Method for the Production of Terminal Alkynes from 1,1-Dibromo-1-alkenes and its Application in the Total Synthesis of Natural Product Dihydroxerulin

Liu, Shihui; et al, Advanced Synthesis & Catalysis, 2015, 357(2-3), 553-560

合成路线：1 步

401514-40-7

_92%

反应条件：

1.1 Reagents: Cesium carbonate Solvents: Dimethyl sulfoxide ; 12 h, 115 °C

参考文献：

Cs2CO3-mediated synthesis of terminal alkynes from 1,1-dibromo-1-alkenes

Zhao, Ming; et al, Tetrahedron Letters, 2011, 52(9), 992-994

合成路线：1 步

401514-40-7

_5%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 2 h, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water ; -78 °C

参考文献：

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

Jeremias, Noah; et al, Organic Letters, 2021, 23(15), 5674-5678

合成路线：1 步

19819-95-5

_84%

反应条件：

1.1 Reagents: Potassium carbonate , Sulfonyl fluoride Solvents: Dimethyl sulfoxide ; 2 h, rt
1.2 Reagents: Cesium fluoride ; rt → 100 °C; 2 h, 100 °C; 100 °C → rt

参考文献：

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Zha, Gao-Feng ; et al, Journal of the American Chemical Society, 2018, 140(50), 17666-17673

合成路线：1 步

2142-68-9

_77%

反应条件：

1.1 Reagents: Pyridine , Phosphorus pentachloride (pyridine-supported) ; 210 s, 110 °C

参考文献：

One-step synthesis of aromatic terminal alkynes from their corresponding ketones under microwave irradiation

Ghaffarzadeh, Mohammad; et al, Synthetic Communications, 2006, 36(14), 1973-1981

合成路线：1 步

342652-04-4

_73%

参考文献：

Simple route from aldehydes to alkynes and 1-chloro-1-alkynes

Villieras, J.; et al, Synthesis, 1975, (7), 458-61

合成路线：1 步

615-41-8

_72%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium ; 18 h, rt
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 4 h, rt

参考文献：

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

Cloutier, Melissa; et al, Organic Letters, 2019, 21(10), 3866-3870

合成路线：2 步

615-41-8

反应条件：

1.1 Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: 1,2-Dichloroethane ; rt; 4 h, 40 °C
2.1 Reagents: Potassium carbonate Solvents: Methanol ; 1 h, rt

参考文献：

Electrochemical Gold-Catalyzed 1,2-Difunctionalization of C-C Multiple Bonds

Kumar, Anil ; et al, Angewandte Chemie, 2023, 62(37),

合成路线：2 步

615-41-8

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: 1,2-Dichloroethane ; rt; 4 h, 40 °C
2.1 Reagents: Potassium carbonate Solvents: Methanol ; 1 h, rt

参考文献：

Electrochemical gold-catalyzed 1,2-difunctionalization of C-C multiple bonds

Kumar, Anil; et al, ChemRxiv, 2023, 1, 1-6

合成路线：1 步

24654-08-8

_66%

反应条件：

1.1 Reagents: Sodium bicarbonate Solvents: Water

参考文献：

Modes of action of phosphorus pentachloride. III. Action on acetylene derivatives

Bergmann, Ernst; et al, Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen, 1933, 66, 278-86

合成路线：1 步

67-72-1

_59%

参考文献：

Regiospecific functionalization of unsaturated compounds via their dilithio derivatives. Part III. Synthesis of o-halophenylacetylenes via the dianion of phenylacetylene

Hommes, H.; et al, Tetrahedron Letters, 1981, 22(26), 2495-6

合成路线：1 步

_59%

反应条件：

1.1 Reagents: Hexachloroethane Solvents: Tetrahydrofuran
1.2 Reagents: Oxonium

参考文献：

Hexachloroethane

Strekowski, Lucjan; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2014, 1, 1-4

合成路线：1 步

反应条件：

1.1 Catalysts: Hexachloroethane Solvents: Tetrahydrofuran

参考文献：

Hexachloroethane

Strekowski, Lucjan; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

合成路线：1 步

128-09-6

参考文献：

Regiospecific functionalization of unsaturated compounds via their dilithio derivatives. Part III. Synthesis of o-halophenylacetylenes via the dianion of phenylacetylene

Hommes, H.; et al, Tetrahedron Letters, 1981, 22(26), 2495-6

合成路线：1 步

187463-09-8

参考文献：

Product class 8: linear alkynes: synthesis by elimination

Sankararaman, S., Science of Synthesis, 2008, 43, 435-467

合成路线：1 步

21047-57-4

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Methanol ; 4 h, rt

参考文献：

Palladium-Catalyzed Oxidative Annulation Leading to Substituted Pyrrolo[3,2,1-jk]carbazoles by Sequential C-N and C-C Bond Formation

Azizzade, Meysam; et al, Organic Letters, 2023, 25(11), 1823-1828

合成路线：1 步

2254065-00-2

反应条件：

1.1 Reagents: Cesium fluoride ; rt → 100 °C; 2 h, 100 °C; 100 °C → rt

参考文献：

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Zha, Gao-Feng ; et al, Journal of the American Chemical Society, 2018, 140(50), 17666-17673

合成路线：1 步

558-13-4

反应条件：

1.1 Reagents: Triphenylphosphine Solvents: Dichloromethane ; 0 °C; 40 min, rt
1.2 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 1 h, -78 °C; 2 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water

参考文献：

Palladium-Catalyzed Tandem C-H Functionalization/Cyclization Strategy for the Synthesis of 5-Hydroxybenzofuran Derivatives

Ichake, Sachin S.; et al, Organic Letters, 2017, 19(1), 54-57

合成路线：2 步

558-13-4

反应条件：

1.1 Reagents: Triphenylphosphine Solvents: Dichloromethane ; 20 min, 0 °C; 10 min, 0 °C
1.2 5 min, 0 °C; 40 min, 0 °C; 0 °C → rt; 40 min, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 2 h, -78 °C
2.2 Reagents: Ammonium chloride Solvents: Water ; -78 °C

参考文献：

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

Jeremias, Noah; et al, Organic Letters, 2021, 23(15), 5674-5678

合成路线：2 步

558-13-4

反应条件：

1.1 Reagents: Triphenylphosphine Solvents: Dichloromethane ; 60 min, 0 °C
2.1 Reagents: Cesium carbonate Solvents: Dimethyl sulfoxide ; 8 h, 115 °C

参考文献：

One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes and Allylamines To Access 2,3-Dihydro-1H-imidazo[1,2-a]indoles

Jin, Hongwei; et al, Synthesis, 2020, 52(9), 1417-1424

合成路线：1 步

90-13-1

参考文献：

Photothermal Oxidative Destruction of Chloronaphthalene

Nimlos, Mark R.; et al, Environmental Science and Technology, 1994, 28(5), 816-22

合成路线：2 步

694-80-4

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ; 25 °C; 24 h, 25 °C
2.1 Reagents: Potassium carbonate Solvents: Methanol ; 3 h, 25 °C

参考文献：

Visible light-induced deoxygenation/cyclization of salicylic acid derivatives and aryl acetylene for the synthesis of flavonoids

Fan, Xiaodong; et al, Chemical Communications (Cambridge, 2022, 58(43), 6348-6351

合成路线：2 步

694-80-4

反应条件：

1.1 Reagents: Diisopropylamine Catalysts: Triphenylphosphine , Palladium chloride , Cuprous iodide ; 1.5 h, 60 °C; 60 °C → 0 °C
1.2 Reagents: Diisopropylamine ; overnight, 60 °C
2.1 Reagents: Potassium carbonate Solvents: Methanol ; 2 h, rt
2.2 Solvents: Water ; rt

参考文献：

The synthesis of [1,2,3]-triazole-based bent core liquid crystals via microwave-mediated 'Click Reaction' and their mesomorphic behaviour

Wang, Kunlun; et al, Liquid Crystals, 2019, 46(2), 257-271

合成路线：2 步

694-80-4

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ; rt; 24 h, rt
2.1 Reagents: Potassium carbonate Solvents: Methanol ; 3 h, rt

参考文献：

Aerobic Oxynitration of Alkynes with tBuONO and TEMPO

Dutta, Uttam; et al, Organic Letters, 2014, 16(24), 6302-6305

合成路线：2 步

95-50-1