Visible-Light, Iodine-Promoted Formation of -Sulfonyl Imines and -Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents.

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 -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 -sulfonyl imines that utilizes stable, widely available reagents.