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Disulfide‐Catalyzed Visible‐Light‐Mediated Oxidative Cleavage of C=C Bonds and Evidence of an Olefin–Disulfide Charge‐Transfer Complex
Author(s) -
Deng Yuchao,
Wei XiaoJing,
Wang Hui,
Sun Yuhan,
Noël Timothy,
Wang Xiao
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201607948
Subject(s) - olefin fiber , photochemistry , photocatalysis , chemistry , visible spectrum , disulfide bond , catalysis , dissociation (chemistry) , oxidative cleavage , cleavage (geology) , charge transfer complex , bond cleavage , organic chemistry , materials science , biochemistry , optoelectronics , fracture (geology) , composite material
A photocatalytic method for the aerobic oxidative cleavage of C=C bonds has been developed. Electron‐rich aromatic disulfides were employed as photocatalyst. Upon visible‐light irradiation, typical mono‐ and multi‐substituted aromatic olefins could be converted into ketones and aldehydes at ambient temperature. Experimental and computational studies suggest that a disulfide–olefin charge‐transfer complex is possibly responsible for the unconventional dissociation of S−S bond under visible light.