Formation of the Tertiary Sulfonamide C(sp3)-N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling

A synthetic strategy for the formation of C(sp(3))-N bonds, particularly through a copper-catalyzed oxidative cross-coupling, is rare. Herein, we report a novel synthetic approach for the preparation of tertiary sulfonamides via copper-catalyzed intra-and intermolecular oxidative C(sp(3))-N cross-coupling reactions. This method allows the utilization of the readily available C(sp(3))-based pinacol boronate as a substrate and the tolerance of a wide range of functional groups under mild reaction conditions. The success of this strategy relies on the unprecedented additive effects of silanol and NaIO4 .

Automated summary

This rare synthetic strategy utilizes a copper-catalyzed oxidative cross-coupling to form C(sp(3))-N bonds, allowing the preparation of tertiary sulfonamides. The method is tolerant of a wide range of functional groups under mild conditions and relies on the additive effects of silanol and NaIO4.