Palladium-catalyzed synthesis of S-aryl thiocarbamates via desulfurative C–S cross-coupling reaction of dithiocarbamates

Abstract

A new protocol has been demonstrated here for synthesizing S-aryl thiocarbamates via the desulfurative C–S cross coupling of dithiocarbamate esters with arylsilanes in the presence of a Pd(II)-catalyst and a Cu(II)-oxidant. A series of S-aryl thiocarbamates have been prepared by using several dithiocarbamate esters containing cyclic and acyclic secondary amines and arylsilanes with different substituents. A probable mechanistic pathway has been proposed based on a control experiment and spectroscopic analysis. Post-synthetic modification of S-aryl thiocarbamates allows exchange of S-aryl groups with suitable aromatic thiols via C–S single bond cleavage.