Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides

被引：26

作者：

Luo, Ziwei ^{[1
]}

Yang, Xinkan ^{[1
]}

Tsui, Gavin Chit ^{[1
]}

机构：

[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 15期

关键词：

METAL-FREE TRIFLUOROMETHYLTHIOLATION; ARYL BORONIC ACIDS; DECARBOXYLATIVE TRIFLUOROMETHYLTHIOLATION; CATALYZED TRIFLUOROMETHYLTHIOLATION; SILVER(I) TRIFLUOROMETHANETHIOLATE; NUCLEOPHILIC TRIFLUOROMETHYLATION; SUBSTITUENT CONSTANTS; TERMINAL ALKYNES; FLUORINE; TRIMETHYLSILANE;

D O I：

10.1021/acs.orglett.0c02235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of perfluoroalkyl sulfides is described. The method employs stable and readily accessible thiosulfonates as new electrophiles with commercial nucleophilic perfluoroalkylating reagents. The mild reaction conditions allow access to a wide variety of both aryl- and alkyl-substituted perfluoroalkyl sulfides amenable to pharmaceutical development. Furthermore, the reaction operation is straightforward, odorless, does not produce toxic wastes, and, therefore should appeal to practitioners in industrial-scale productions.

引用

页码：6155 / 6159

页数：5

共 82 条

[1]

[Anonymous], 2008, J MED CHEM, V51, P4359

[2] Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides [J].

Baert, Francois ;

Colomb, Julie ;

Billard, Thierry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10382-10385

[3] Late stage trifluoromethylthiolation strategies for organic compounds [J].

Barata-Vallejo, Sebastian ;

Bonesi, Sergio ;

Postigo, Al .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) :7150-7182

[4] Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates [J].

Billard, T ;

Large, S ;

Langlois, BR .

TETRAHEDRON LETTERS, 1997, 38 (01) :65-68

[5] A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides [J].

Billard, T ;

Langlois, BR .

TETRAHEDRON LETTERS, 1996, 37 (38) :6865-6868

[6] 18F-Fluoroform: a 18F-trifluoromethylating agent for the synthesis of SCF2 18F-aromatic derivatives [J].

Carbonnel, Elodie ;

Besset, Tatiana ;

Poisson, Thomas ;

Labar, Daniel ;

Pannecoucke, Xavier ;

Jubault, Philippe .

CHEMICAL COMMUNICATIONS, 2017, 53 (42) :5706-5709

[7] Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C-H Bonds via Nondirected Oxidative C(sp3)-H Activation [J].

Chen, Chao ;

Xu, Xiu-Hua ;

Yang, Bin ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2014, 16 (12) :3372-3375

[8] Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur [J].

Chen, Chao ;

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12454-12457

[9] Sandmeyer trifluoromethylthiolation of arenediazonium salts with sodium thiocyanate and Ruppert-Prakash reagent [J].

Danoun, Gregory ;

Bayarmagnai, Bilguun ;

Gruenberg, Matthias F. ;

Goossen, Lukas J. .

CHEMICAL SCIENCE, 2014, 5 (04) :1312-1316

[10] Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers [J].

Exner, Benjamin ;

Bayarmagnai, Bilguun ;

Jia, Fan ;

Goossen, Lukas J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (48) :17220-17223

← 1 2 3 4 5 6 7 8 9 →