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Defluorinative alkylation of 1-trifluoromethyl alkenes with alkyl radicals derived from visible light-induced deoxygenation of xanthate salts: synthesis of gem -difluoroalkenes.

Xin LiYan JiaoLifei HanJinwei SunXuan Zhang
Published in: Organic & biomolecular chemistry (2023)
Catalyst- and metal-free difluoroallylation of alkyl precursors with trifluoromethyl alkenes for the synthesis of gem -difluoroalkenes is appealing and challenging. We herein describe a visible light-induced approach that enables deoxygenative difluoroallylation of abundant alcohols via xanthate salts with trifluoromethyl alkenes, where xanthate salts work as a photoreductant and an alkylating reagent, avoiding the use of external catalysts. This one-pot method can accommodate primary, secondary and tertiary alcohols with good functionality tolerance and be successfully applied to the late-stage functionalization of natural products and drugs.
Keyphrases
  • ionic liquid
  • room temperature
  • highly efficient
  • visible light
  • metal organic framework