Metal-free amidation of ether sp3 C–H bonds with sulfonamides using PhI(OAc)2

Abstract

A selective protocol for the metal-free α-C–H amidation of ethers using sulfonamides and hypervalent iodine oxidants has been developed. The absence of precious metals and the conditions employed make the method environmentally attractive. A number of cyclic and acyclic, linear and branched ethers have been successfully amidated, and a broad sulfonamide scope has been demonstrated. Two unusual reactions, namely the amidation of an unactivated tert-butyl group and a tandem C–C coupling reaction, are also described.