Teaching an Old Reagent New Tricks: Direct Aminosulfonylation of Electron-rich (hetero)Arenes Utilizing tert-Butyl Chlorosulfonylcarbamate with Diisopropylethylamine

Sulfonamides, especially primary aryl sulfonamides are very important scaffolds not only because of the wide applications as pharmacophores in drugs, but also the derivatization for other sulfonamides and different sulfur-containing compounds. Among the 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, by the proposed and unique tert-butyl sulfonylcarbamate intermediate generated in situ from easily accessed tert-butyl chlorosulfonylcarbamate and diisopropylethylamine, a catalyst-free, mild and very pratical aminosulfonylation protocol for a wide scope of electron-rich (hetero)arene substrates with good to excellent yields was reported.