Site‐Selective Remote Radical C−H Functionalization of Unactivated C−H Bonds in Amides Using Sulfone Reagents

Abstract

Abstract A general and practical strategy for remote site‐selective functionalization of unactivated aliphatic C−H bonds in various amides by radical chemistry is introduced. C−H bond functionalization is achieved by using the readily installed N‐allylsulfonyl moiety as an N‐radical precursor. The in situ generated N‐radical engages in intramolecular 1,5‐hydrogen atom transfer to generate a translocated C radical which is subsequently trapped with various sulfone reagents to afford the corresponding C−H functionalized amides. The generality of the approach is documented by the successful remote C−N 3 , C−Cl, C−Br, C−SCF 3 , C−SPh, and C−C bond formation. Unactivated tertiary and secondary C−H bonds, as well as activated primary C−H bonds, can be readily functionalized by this method.