Organocatalytic electrochemical synthesis of α-quaternary amino aldehydes

Abstract

α-Quaternary amino aldehydes are highly valuable synthetic targets in synthetic and medicinal chemistry, yet the efficient synthesis of sterically hindered α-quaternary amino aldehydes, especially for amino drug modification, remains a significant challenge. Herein, we report an efficient electrochemical organocatalytic method for the direct α-sulfonamidation of aldehydes, providing straightforward access to these scaffolds with broad substrate scope and excellent functional group tolerance. This protocol demonstrates significant utility in the late-stage modification of sulfonamide drugs and affords versatile products that can be readily transformed into diverse synthetically valuable building blocks. Mechanistic studies support a cationic nucleophilic addition pathway and in situ generated hypobromite would act as an oxidative mediator.