Photoredox-Controlled Mono- and Di-Multifluoroarylation of C(sp3)-H Bonds with Aryl Fluorides

A controllable mono-and di-multifluoroarylation of acyclic and cyclic N-aryl amines with aryl fluorides by photocatalyzed dual C(sp(3))-H/C(sp(2))-F functionalization has been developed, providing new access to a wide array of valuable alpha-fluoroarylated amines. In addition, the one-pot consecutive hetero-di-multifluoroarylation of N-aryl pyrrolidines and N,N-dimethylanilines was achieved with high to excellent diastereoselectivity. This new defluorinative C(sp(3))-C(sp(2)) coupling is distinguished by a broad scope, good regioselectivity, and mild conditions as well as gram-scale and late-stage applicability, and thus constitutes a significant advance in the arylation of unactivated C(sp(3))-H bonds with aryl fluorides.