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Direct Photoredox‐Catalyzed Reductive Difluoromethylation of Electron‐Deficient Alkenes
Author(s) -
Tang XiaoJun,
Zhang Zuxiao,
Dolbier William R.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504363
Subject(s) - trimethylsilyl , chemistry , silane , nucleophile , radical , catalysis , photoredox catalysis , tin , tris , reductive elimination , medicinal chemistry , photochemistry , catalytic cycle , electron , combinatorial chemistry , organic chemistry , physics , photocatalysis , biochemistry , quantum mechanics
Photoredox‐catalyzed reductive difluoromethylation of electron‐deficient alkenes was achieved in one step under tin‐free, mild and neutral conditions. This protocol affords a facile method to introduce RCF 2 (R=H, Ph, Me, and CH 2 N 3 ) groups at sites β to electron‐withdrawing groups. It was found that TTMS (tris(trimethylsilyl)silane) served nicely as both the H‐atom donor and the electron donor in the catalytic cycle. Experimental and DFT computational results provided evidence that RCF 2 (R=H, Ph, Me) radicals are nucleophilic in nature.