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N‐Heterocyclic Carbene Catalyzed γ‐Dihalomethylenation of Enals by Single‐Electron Transfer
Author(s) -
Yang Wen,
Hu Weimin,
Dong Xiuqin,
Li Xin,
Sun Jianwei
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608371
Subject(s) - carbene , regioselectivity , catalysis , chemistry , intermolecular force , radical , combinatorial chemistry , electron transfer , organocatalysis , electron , photochemistry , organic chemistry , molecule , enantioselective synthesis , physics , quantum mechanics
An N‐heterocyclic carbene (NHC) catalyzed dihalomethylenation of enals is described. It is a rare example of merging NHC catalysis with single‐electron chemistry, a challenging topic with limited previous success. The versatile carbon‐centered trihalomethyl radicals have been demonstrated, for the first time, to be compatible with an NHC‐bound intermediate, thus leading to efficient and regioselective intermolecular C−C bond formation. The mild process provides straightforward access to unsaturated δ,δ‐dihalo esters.