88284-48-4 (2-(三甲基硅)苯基三氟甲烷磺酸盐,2-(Trimethylsilyl)phenyl trifluoromethanesulfonate)

_90%

反应条件：

1.1 Reagents: Pyridine Solvents: Dichloromethane ; 0 °C; 2 h, 0 °C

参考文献：

Improved synthesis of the benzyne precursor 2-(trimethylsilyl)phenyl trifluoromethanesulfonate

Atkinson, Darcy J.; et al, Synthesis, 2010, (6), 911-913

合成路线：1 步

_84%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 40 min, -78 °C
1.2 -78 °C; 40 min, -78 °C; -78 °C → rt; 20 min, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

Stereoretentive ring-opening metathesis polymerization to access all-cis poly(p-phenylene vinylene)s with living characteristics

Hsu, Ting-Wei; et al, ChemRxiv, 2020, 1, 1-7

合成路线：1 步

_94%

反应条件：

1.1 Solvents: Tetrahydrofuran ; 90 min, reflux
1.2 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -100 °C; 20 min, -100 °C → -80 °C; -80 °C → -100 °C
1.3 -100 °C; 20 min, -100 °C → -80 °C
1.4 Reagents: Sodium bicarbonate Solvents: Water ; cooled

参考文献：

Synthesis of aryl stannanes from silyl triflates via aryne intermediates

Lakshmi, B. Vasantha; et al, Synlett, 2011, (3), 345-348

合成路线：1 步

_92%

反应条件：

1.1 45 min, 80 °C
1.2 Solvents: Tetrahydrofuran ; rt → -100 °C
1.3 Reagents: Butyllithium ; -100 °C; 20 min, -100 °C → -80 °C; -80 °C → -100 °C
1.4 -100 °C; 20 min, -100 °C → -80 °C

参考文献：

An efficient procedure for the synthesis of ortho-trialkylsilylaryl triflates: easy access to precursors of functionalized arynes

Pena, Diego; et al, Synthesis, 2002, (10), 1454-1458

合成路线：1 步

_87%

反应条件：

1.1 Solvents: Tetrahydrofuran ; rt; 3 h, reflux; reflux → rt
1.2 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -100 °C; 20 min, -100 °C → -78 °C; -78 °C → -100 °C
1.3 -100 °C; 20 min, -100 °C → -78 °C
1.4 Reagents: Sodium bicarbonate Solvents: Water ; cooled

参考文献：

Acetic Acid Promoted Metal-Free Aerobic Carbon-Carbon Bond Forming Reactions at α-Position of Tertiary Amines

Ueda, Hirofumi; et al, Organic Letters, 2014, 16(16), 4194-4197

合成路线：1 步

36601-47-5

_91%

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether ; 1 min, rt
1.2 Solvents: Diethyl ether ; 7.3 s, rt
1.3 Reagents: Sodium carbonate Solvents: Water

参考文献：

Continuous-Flow Synthesis of Trimethylsilylphenyl Perfluorosulfonate Benzyne Precursors

Michel, Boris; et al, Organic Letters, 2014, 16(10), 2684-2687

合成路线：1 步

36601-47-5

_90%

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether , Hexane ; 79.2 s, rt
1.2 Solvents: Diethyl ether ; 67 min, rt
1.3 Reagents: Sodium carbonate Solvents: Water ; rt

参考文献：

One-Pot Synthesis of Heteroatom-Bridged Cyclic Diaryliodonium Salts

Damrath, Mattis; et al, Organic Letters, 2022, 24(13), 2562-2566

合成路线：1 步

_86%

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether ; 4 h, 0 °C → rt
1.2 overnight, 0 °C → rt

参考文献：

Trifluoromethanesulfonic anhydride

Martinez, Antonio Garcia; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2016, 1, 1-17

合成路线：1 步

_73%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -100 °C; 20 min, -100 °C → -78 °C; -78 °C → -100 °C
1.2 -100 °C; 20 min, -100 °C → -78 °C
1.3 Reagents: Sodium bicarbonate Solvents: Water ; cooled

参考文献：

Access to Highly Functionalized Indanes from Arynes and α,γ-Diketo Esters

Hu, Wanyao; et al, Organic Letters, 2019, 21(4), 941-945

合成路线：1 步

反应条件：

参考文献：

Acetic Acid Promoted Metal-Free Aerobic Carbon-Carbon Bond Forming Reactions at α-Position of Tertiary Amines

Ueda, Hirofumi; et al, Organic Letters, 2014, 16(16), 4194-4197

合成路线：1 步

_84%

反应条件：

1.1 Solvents: Tetrahydrofuran ; 4 h, 80 °C; 80 °C → rt
1.2 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 40 min, -78 °C
1.3 -78 °C; 40 min, -78 °C; -78 °C → rt; 20 min, rt
1.4 Reagents: Sodium bicarbonate Solvents: Water ; cooled

参考文献：

Stereoretentive Ring-Opening Metathesis Polymerization to Access All-cis Poly(p-phenylenevinylene)s with Living Characteristics

Hsu, Ting-Wei; et al, Journal of the American Chemical Society, 2020, 142(28), 11983-11987

合成路线：1 步

_66%

反应条件：

1.1 Reagents: Triethylamine , Isopropyl isocyanate Solvents: Dichloromethane ; 2 h, 23 °C
1.2 Reagents: N,N,N′,N′-Tetramethylethylenediamine , (1,1-Dimethylethyl)dimethylsilyl 1,1,1-trifluoromethanesulfonate Solvents: Diethyl ether , Pentane ; 5 min, 0 °C; 30 min, 0 °C → 23 °C
1.3 Reagents: N,N,N′,N′-Tetramethylethylenediamine ; 23 °C → -78 °C
1.4 Reagents: Butyllithium Solvents: Hexane ; 70 min, -78 °C; 1 h, -78 °C
1.5 35 min, -78 °C; 85 min, -78 °C
1.6 Reagents: Sodium bisulfate Solvents: Water ; 45 min, -78 °C → 23 °C
1.7 Reagents: Diethylamine , 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetonitrile ; 45 min, 40 °C; 40 °C → 23 °C
1.8 Solvents: Acetonitrile ; 20 min, 23 °C; 2 h, 23 °C
1.9 Reagents: Sodium bicarbonate , Sodium bisulfate Solvents: Water ; 23 °C

参考文献：

Efficient Synthesis of 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate: A Versatile Precursor to o-Benzyne

Bronner, Sarah M.; et al, Journal of Organic Chemistry, 2009, 74(22), 8842-8843

合成路线：1 步

反应条件：

1.1 Reagents: Bromine Solvents: Acetic acid ; 30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ; 2 h, 70 °C
1.3 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 1 h, -78 °C
1.4 -78 °C; 1 h, -78 °C
1.5 Reagents: Sodium bicarbonate Solvents: Water ; cooled

参考文献：

Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

Lei, Meng; et al, Tetrahedron Letters, 2019, 60(20), 1389-1392

合成路线：1 步

37595-74-7

反应条件：

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 3 h, rt

参考文献：

Dual Nickel-/Palladium-Catalyzed Reductive Cross-Coupling Reactions between Two Phenol Derivatives

Xiong, Baojian; et al, Organic Letters, 2020, 22(16), 6334-6338

合成路线：1 步

37595-74-7

反应条件：

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 3 h, rt

参考文献：

Dual nickel/palladium-catalyzed reductive cross-coupling reactions between two phenol derivatives

Xiong, Baojian; et al, ChemRxiv, 2020, 1, 1-8

合成路线：1 步

参考文献：

1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines

Cho, Seoyoung; et al, Organic Letters, 2020, 22(4), 1670-1674

合成路线：1 步

7440-44-0

反应条件：

1.1 Reagents: Cesium fluoride , 18-Crown-6 Solvents: Acetonitrile , 1,2-Dichlorobenzene ; overnight, 70 °C

参考文献：

Cycloaddition of benzyne to SWCNT: towards CNT-based paddle wheels

Criado, Alejandro; et al, Chemical Communications (Cambridge, 2010, 46(37), 7028-7030

合成路线：1 步

参考文献：

Assembly of polyfunctional arenes with three contiguous and different substituents by Pd-catalyzed four-component reactions

Shen, Yong; et al, Cell Reports Physical Science, 2021, 2(11),

合成路线：1 步

参考文献：

Aerobic Cu-catalyzed oxidative 1 : 2 coupling of benzynes with terminal alkynes

Lu, Tianhao; et al, Chemical Communications (Cambridge, 2020, 56(59), 8214-8217

合成路线：1 步

参考文献：

Copper-Mediated Trifluoromethylation-Allylation of Arynes

Yang, Xinkan; et al, Organic Letters, 2018, 20(4), 1179-1182

合成路线：2 步

107-46-0

反应条件：

1.1 Solvents: Tetrahydrofuran ; 2 h, 85 °C
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; 20 min, -80 °C
2.2 -78 °C; 30 min, rt
2.3 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

Regioselective synthesis of 2-(2-hydroxyaryl)pyridines from the reactions of benzynes with pyridine N-oxides

Shaibu, Balagopal S.; et al, Organic & Biomolecular Chemistry, 2012, 10(34), 6834-6839

合成路线：2 步

108-95-2

反应条件：

1.1 Reagents: Bromine Solvents: Acetic acid ; 0 °C; 30 min, 0 °C
2.1 Solvents: Tetrahydrofuran ; 2 h, reflux; reflux → rt
2.2 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1.5 h, -78 °C
2.3 -78 °C; 2 h, -78 °C
2.4 Reagents: Sodium bicarbonate Solvents: Water ; -78 °C

参考文献：

Copper-Mediated Cascade C-H/N-H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids

Zhang, Ting-Yu; et al, Organic Letters, 2018, 20(1), 220-223

合成路线：2 步

17881-65-1

75-77-4

反应条件：

1.1 Reagents: Sodium Solvents: Toluene ; 4 h, 110 °C; 30 min, 110 °C; 110 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Methanol , Water ; neutralized, rt
2.1 Reagents: Pyridine Solvents: Dichloromethane ; 2 h, 0 °C; 0 °C → rt; 2 h, rt
2.2 Solvents: Water ; rt

参考文献：

Alkyl substituted [2.2]paracyclophane-1,9-dienes

Lidster, Benjamin J.; et al, Organic & Biomolecular Chemistry, 2016, 14(25), 6079-6087

合成路线：2 步

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; rt; 30 min, rt
2.1 Reagents: Pyridine Solvents: Dichloromethane ; 0 °C; 2 h, 0 °C

参考文献：

Improved synthesis of the benzyne precursor 2-(trimethylsilyl)phenyl trifluoromethanesulfonate

Atkinson, Darcy J.; et al, Synthesis, 2010, (6), 911-913

合成路线：2 步

36601-47-5

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
2.1 Reagents: Pyridine Solvents: Dichloromethane

参考文献：

Benzynes in Natural Product Synthesis

Hunter, Ruth F., 1989, , ,

合成路线：2 步

75-77-4