Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp²)–H, C(sp³)–H, and Late-Stage Functionalizations

Abstract

Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C­(sp²)–H bonds of (hetero)­arenes and alkenes, as well as unactivated C­(sp³)–H bonds under Rh^III catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope (not limited to strongly heterocyclic coordinating groups), and tolerance of valuable functional substituents, such as unprotected amine and hydroxyl groups. The synthetic applicability of this protocol is also demonstrated by late-stage functionalization of biologically important scaffolds