Nickel-catalyzed direct formation of the C–S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent

Abstract

Various unsymmetrical aryl sulfides were synthesized by nickel-catalyzed C–S bond formation in good to excellent yields. The reactions employed arylsulfonyl chlorides as an aryl thiol source and Mn dust as a reducing agent. The scope and versatility of the method have been successfully demonstrated with 42 examples. Mechanistic studies revealed the existence of an intermediate disulfide substance. A catalytic cycle was proposed including a three-step reduction by Mn for the achievement of the reaction, and Ni(0) and Ni(I) species were supposed to be involved in the reaction mechanism.