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

Abstract

Abstract A 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 H 2 O 2 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 H 2 O 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