Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes, sulfonamides, and PhI(OAc)₂ under practical and mild reaction conditions has been developed. According to mechanistic studies described within, the reaction proceeds through an initial step involving a radical initiator (generated either by visible-light or heat) to activate the reacting substrates. The reaction provides a synthetically useful and operationally simple, relatively mild alternative to the traditional formation of N-sulfonyl imines that utilizes stable, widely available reagents.
Keywords: N-sulfonyl imine; aldimine synthesis; hypervalent iodine; iminoiodinane; iodine promoted; iodobenzene diacetate (PIDA); nitrogen-centered radical; sulfonamide; visible-light.