Palladium-catalyzed Synthesis of S-Aryl Thiocarbamate via Desulfurative C-S Cross-coupling Reaction of Dithiocarbamates

Abstract

A new protocol for synthesizing S-aryl thiocarbamate has been demonstrated here by the desulfurative C-S cross coupling of dithiocarbamate esters with arylsilanes in presence of Pd(II)-catalyst and 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 control experiment and spectroscopic analysis. Post-synthetic modification of S-aryl thiocarbamate allows exchange of S-aryl group with suitable aromatic thiol via C-S single bond cleavage.