Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

Abstract

Aryl iodides and aryl sulfonyl hydrazides were reacted with carbon monoxide in the presence of DBU and a palladium catalyst to provide optimal yields ofS-aryl thioesters. Aryl sulfonyl hydrazides served as aryl thiol surrogates. Optimal results were obtained when the reaction was carried out with Pd(dba)(2)/dppb in toluene at 80 degrees C for 12 h. The methodology exhibits superior functional group tolerance, being compatible with moieties like fluoride, chloride, bromide, ester, ketone, cyanide and nitro.