Direct aminosulfonylation of electron-rich (hetero)arenes utilizing tert-butyl chlorosulfonylcarbamate and diisopropylethylamine†

Abstract

Sulfonamides, especially primary aryl sulfonamides, are very important scaffolds not only because of their wide applications as pharmacophores in drugs, but also their derivatization into other sulfonamides and different sulfur-containing compounds. Among aryl sulfonamides, most syntheses of electron-rich (hetero)aryl sulfonamides are still severely limited by the classic chlorosulfonation or oxidative chlorination reactions with significant drawbacks. In this work, using the proposed and unique tert-butyl sulfonylcarbamate intermediate generated in situ from easily accessible tert-butyl chlorosulfonylcarbamate and diisopropylethylamine, a catalyst-free, mild and very practical aminosulfonylation protocol for a wide range of electron-rich (hetero)arene substrates with good to excellent yields was reported.