Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)₂–H Coupling

Abstract

We here have developed an S(O)2–N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet nitrene and followed coupling with sulfonyl radicals in situ to achieve structurally diverse benzenesulfinamides in good yields.

Keywords

• aryl azides
• arylsulfinic acids
• copper/visible light catalysis
• S(O)₂–N coupling
• benzenesulfinamide derivatives