Premium
Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal‐Free C(sp 3 )–C(sp 3 ) Cleavage and Allylation/Alkenylation
Author(s) -
Zhang Jing,
Li Yang,
Xu Ruoyu,
Chen Yiyun
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707171
Subject(s) - alkoxy group , chemistry , cleavage (geology) , acceptor , radical , metal , bond cleavage , photochemistry , stereochemistry , medicinal chemistry , catalysis , organic chemistry , alkyl , materials science , physics , fracture (geology) , composite material , condensed matter physics
The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex‐enabled alkoxyl radical generation under metal‐free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N ‐alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp 3 )‐C(sp 3 ) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst‐free approach with linear primary, secondary, and tertiary alkoxyl radicals.