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Oxidative Coupling of Enamines and Disulfides via Tetrabutylammonium Iodide/ tert‐ Butyl Hydroperoxide‐Mediated Intermolecular Oxidative C( sp 2 )S Bond Formation Under Transition Metal‐Free Conditions
Author(s) -
Sun Jiyun,
ZhangNegrerie Daisy,
Du Yunfei
Publication year - 2016
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.201501099
Subject(s) - chemistry , intermolecular force , enamine , oxidative phosphorylation , oxidative coupling of methane , catalysis , photochemistry , iodide , medicinal chemistry , organic chemistry , molecule , biochemistry
The reaction of enamine compounds with disulfides in the presence of tert ‐butyl hydroperoxide and a catalytic amount of tetrabutylammonium iodide conveniently afforded a variety of α ‐thioenamine compounds through the intermolecular oxidative C( sp 2 )S coupling. Incorporating both of the sulfide moieties in the disulfides into the final products under oxidative conditions, this novel approach exhibits the feature of atom efficiency. A radical mechanistic pathway for the reaction process has been proposed.