Article Dans Une Revue Tetrahedron Letters Année : 2010

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

Résumé

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.

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hal-05123389 , version 1 (20-06-2025)

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Yohan Macé, Charlotte Pradet, Matthew Popkin, Jean-Claude Blazejewski, Emmanuel Magnier. Mechanistical insight into ‘electrophilic’ trifluoromethylation with S-(trifluoromethyl)dibenzothiophenium salts. Tetrahedron Letters, 2010, 51 (41), pp.5388-5391. ⟨10.1016/j.tetlet.2010.07.154⟩. ⟨hal-05123389⟩
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