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Copper‐Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S‐Arylation through Disulfide‐Directed C−H Activation
Author(s) -
Wang Dawei,
Yu Xin,
Yao Wei,
Hu Wenkang,
Ge Chenyang,
Shi Xiaodong
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600597
Subject(s) - thiophenol , chemistry , catalysis , disulfide bond , hydroxylation , combinatorial chemistry , copper , organic chemistry , enzyme , biochemistry
Copper‐catalyzed thiophenol C−H activation is described. Through an initial attempt to conduct C‐arylation with arylboronic acid, a rather surprising sequential C−H activation and S‐arylation was discovered. Mechanistic investigation revealed the disulfide intermediate as the key component in directing C−H oxidation. The overall reaction proceeded under mild conditions with molecular oxygen as the oxidant. Discovery of disulfide as the directing group provides a potential new direction for catalytic C−H functionalization under mild conditions.