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

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 tr...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 51; no. 41; pp. 5388 - 5391
Main Authors Macé, Yohan, Pradet, Charlotte, Popkin, Matthew, Blazejewski, Jean-Claude, Magnier, Emmanuel
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.10.2010
Elsevier
Subjects
Chemistry
Chemistry, Organic
Ethers
Mechanistic studies
Nucleophiles
Physical Sciences
Radical pathway
Radicals
Reaction mechanisms
Science & Technology
Sulfonium salts
Tetrahedrons
Trapping
Trifluoromethylation reaction
Trifluoromethylation reaction
Sulfonium salts
Radical pathway
Mechanistic studies
HALIDES
SULFIDES
REACTIVITY
ETHERS
CHEMISTRY
FLUORINE
BROMOTRIFLUOROMETHANE
AGENTS
PERFLUOROALKYL IODIDES
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.07.154