Oxidative Coupling of Enamines and Disulfides via Tetrabutylammonium Iodide/tert‐Butyl Hydroperoxide‐Mediated Intermolecular Oxidative C(sp2)S Bond Formation Under Transition Metal‐Free Conditions

Abstract 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. magnified image