Solvent Controlled Transformation between Sulfonyl Hydrazides and Alkynes: Divergent Synthesis of Benzo[b]thiophene‐1,1‐dioxides and (E)‐β‐iodo Vinylsulfones

Abstract

AbstractA green, efficient and controllable transformation between sulfonyl hydrazides and alkynes leading to benzo[b]thiophene‐1,1‐dioxides and (E)‐β‐iodo vinylsulfones via radical pathway has been developed. The reaction occurs rapidly in the presence of simply H2O2 and KI without the help of any transition metal. The chemoselectivity of the reaction is determined by the solvent in which the process is performed: TFE favors the cyclic product, while H2O medium generates the iodosulfonylative product. Notably, this protocol also represents the first direct approach to the aggregation‐induced‐emmision (AIE) active benzo[b]thiophene‐1,1‐dioxides from readily available sulfonyl hydrazides and alkynes in one step.magnified image