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Photocatalytic Neophyl Rearrangement and Reduction of Distal Carbon Radicals by Iminyl Radical‐Mediated C−C Bond Cleavage
Author(s) -
Yu XiaoYe,
Wang PengZi,
Yan DongMei,
Lu Bin,
Chen JiaRong,
Xiao WenJing
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800834
Subject(s) - chemistry , radical , photocatalysis , photochemistry , bond cleavage , cleavage (geology) , carbon fibers , selectivity , catalysis , organic chemistry , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material
The control of selectivity in the reactions of the highly reactive open‐shell carbon radicals is an attractive but often challenging task. Building on the strategy of photoinduced iminyl radical‐mediated C−C bond cleavage, we have developed photocatalytic neophyl rearrangement and reduction of distal carbon radicals under visible light irradiation of O ‐acyl oximes. This mild protocol tolerates a wide range of readily available O ‐acyl oximes, enabling facile synthesis of diversely substituted α,β ‐unsaturated nitriles and β ‐functionalized saturated nitriles in a highly selective manner.