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...

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Bibliographic Details
Published in:Tetrahedron letters 2010-10, Vol.51 (41), p.5388-5391
Main Authors: Macé, Yohan, Pradet, Charlotte, Popkin, Matthew, Blazejewski, Jean-Claude, Magnier, Emmanuel
Format: Article
Language:English
Subjects:
Ethers
Mechanistic studies
Nucleophiles
Radical pathway
Radicals
Reaction mechanisms
Sulfonium salts
Tetrahedrons
Trapping
Trifluoromethylation reaction
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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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.07.154