Copper-catalyzed remote C(sp3)-H heteroarylation of N-fluorocarboxamides with azoles

Abstract

A general protocol for intermolecular distal C(sp³)-H heteroarylation of N-fluorocarboxamides with azoles under copper catalysis has been accomplished. Notably, both benzylic C(sp³)-H bonds and aliphatic C(sp³)-H bonds in carboxamides could conduct reactions smoothly and exhibited remarkable regioselectivity. This cross-dehydrogenative coupling reaction involved a sequential course of amidyl radical generation, 1,5-hydrogen atom transfer (HAT), and heteroarylation steps. This approach was capable of accomplishing the heteroarylation reaction of the distal carbon-hydrogen bonds of amides by simultaneously activating C(sp²)-H and C(sp³)-H, avoiding the utilization of pre-functionalized heteroarenes.