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Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp 3 )−H Functionalization under Mild Reaction Conditions
Author(s) -
Zhang Jing,
Li Yang,
Zhang Fuyuan,
Hu Chenchen,
Chen Yiyun
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510014
Subject(s) - chemoselectivity , chemistry , radical , surface modification , alkoxy group , catalysis , hydrogen atom abstraction , substrate (aquarium) , photoredox catalysis , photochemistry , hydrogen atom , combinatorial chemistry , organic chemistry , alkyl , photocatalysis , oceanography , geology
Reported herein is the first visible‐light‐induced formation of alkoxyl radicals from N‐alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp 3 )−H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp 3 )−H functionalization reaction effectively with high regio‐ and chemoselectivity.