Electrochemical access to aryl sulfides from aryl thiols and electron-rich arenes with the potassium iodide as a mediator

Abstract

An indirect electrooxidation method catalyzed by potassium iodide at a low potential for the synthesis of aryl sulfides from aryl thiols and electron-rich arenes has been developed. Cyclic voltammetry was carried out to investigate the electrocatalytic activity of KI for sulfenylation of 1,3,5-trimethoxybenzene. On the basis of in situ FTIR data, cyclic voltammetry and control experiments, the reaction mechanism involving redox chemistry of KI and generation of intermediate 1,2-bis(4-chlorophenyl)disulfane during the reaction was proposed. Under the optimal conditions, various aryl thiols react with electron-rich arenes to afford the corresponding aryl sulfides in 28–92% isolated yields.