Remote Radical Trifluoromethylation: A Unified Approach to the Selective Synthesis of γ-Trifluoromethyl α,β-Unsaturated Carbonyl Compounds - Institut des Sciences Moléculaires de Marseille Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2022

Remote Radical Trifluoromethylation: A Unified Approach to the Selective Synthesis of γ-Trifluoromethyl α,β-Unsaturated Carbonyl Compounds

Résumé

Site-selective trifluoromethylation of silyl dienol ethers derived from α,β-unsaturated aldehydes, ketones, and amides was achieved for the first time in the remote γ position. This photoredox catalyzed process is quite general to compounds bearing many functionalities and is applicable to the late-stage functionalization of biorelevant molecules. The use of S-perfluoroalkyl sulfoximines as ·RF radical sources enables the generalization of the reaction to other perfluoroalkyl groups (RF = CF2H, C4F9). Importantly, an unprecedented enantioselective C(sp3)–H perfluoroalkylation process is disclosed.

Domaines

Chimie organique
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Dates et versions

hal-03936896 , version 1 (14-03-2023)

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Marina Briand, Linh Thai, Flavien Bourdreux, Nicolas Vanthuyne, Xavier Moreau, et al.. Remote Radical Trifluoromethylation: A Unified Approach to the Selective Synthesis of γ-Trifluoromethyl α,β-Unsaturated Carbonyl Compounds. Organic Letters, 2022, 24 (51), pp.9375-9380. ⟨10.1021/acs.orglett.2c03676⟩. ⟨hal-03936896⟩
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