Mechanistical insight into 'electrophilic' trifluoromethylation with S-(trifluoromethyl)dibenzothiophenium salts

被引：27

作者：

Mace, Yohan ^{[1
]}

Pradet, Charlotte ^{[2
]}

Popkin, Matthew ^{[2
]}

Blazejewski, Jean-Claude ^{[1
]}

Magnier, Emmanuel ^{[1
]}

机构：

[1] Univ Versailles St Quentin en Yvelines, Inst Lavoisier Versailles, UMR CNRS 8180, F-78035 Versailles, France

[2] GlaxoSmithKline, Synthet Chem, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 41期

关键词：

Trifluoromethylation reaction; Radical pathway; Mechanistic studies; Sulfonium salts; PERFLUOROALKYL IODIDES; FLUORINE; HALIDES; BROMOTRIFLUOROMETHANE; REACTIVITY; CHEMISTRY; SULFIDES; ETHERS; AGENTS;

D O I：

10.1016/j.tetlet.2010.07.154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trifluoromethyl sulfonium salts are widely used for the introduction of a trifluoromethyl group through reaction with a wide range of nucleophiles. Nevertheless, the reaction mechanism is far from obvious and has been the subject of various literature discussions. In this Letter, we show, through trapping experiments with a radical probe that, at least in the case of nucleophiles such as enol silyl ethers, the reaction proceeds by SET. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5388 / 5391

页数：4

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