Synthesis of α-aryl sulfides by deaminative coupling of α-amino compounds with thiophenols

Abstract

By the deaminative coupling reaction of α-aminoesters and α-aminoacetonitriles with thiols, a new strategy for the synthesis of α-thioaryl esters and nitriles is described, representing an example of converting C(sp³)–N into C(sp³)–S bonds. The substrates form diazo compounds in situ in the presence of NaNO₂, and then a transition-metal-free S–H bond insertion reaction occurs with thiophenol derivatives. The method is simple in operation and post-treatment and has good universality. The corresponding thioethers were obtained in moderate to good (up to 90%) yields under mild conditions.