Modular Synthesis of Sulfonyl Benzoheteroles by Silver-Catalyzed Heteroaromatization of Propargylic Alcohols with p-Toluenesulfonylmethyl Isocyanide (TosMIC): Dual Roles of TosMIC

A new silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC) has been developed that provides an efficient and modular approach to sulfonyl benzoheteroles. For the first time, TosMIC plays a dual role in one reaction: sulfonyl source and ligand. An unprecedented deoxysulfonylation/hydration/condensation reaction pathway is disclosed.