Remote Radical Desaturation of Unactivated C−H Bonds in Amides
Yong Xia, Kalipada Jana, Armido Studer
Abstract
Abstract Desaturation of inert aliphatic C−H bonds in alkanes to form the corresponding alkenes is challenging. In this communication, a new and practical strategy for remote site‐selective desaturation of amides via radical chemistry is reported. The readily installed N‐allylsulfonylamide moiety serves as an N radical precursor. Intramolecular 1,5‐hydrogen atom transfer from an inert C−H bond to the N‐radical generates a translocated C‐radical which is subsequently oxidized and deprotonated to give the corresponding alkene. The commercially available methanesulfonyl chloride is used as reagent and a Cu/Ag‐couple as oxidant. The remote desaturation is realized on different types of unactivated sp 3 ‐C−H bonds. The potential synthetic utility of this method is further demonstrated by the dehydrogenation of natural product derivatives and drugs.