Fluoroamide-Directed Regiodivergent C-Alkylation of Nitroalkanes

Herein, by exploiting different activation modes of fluoroamides, we achieved α- and δ-C(sp3)–H alkylation of nitroalkanes with switchable regioselectivity. Cu catalysis enabled the interception of a distal C-centered radical by a N-centered radical to couple nitroalkanes and unactivated δ-C–H bonds. In addition, imines generated in situ by fluoroamides were trapped by nitroalkanes to realize the α-C–H alkylation of amides. Both of those scalable protocols have broad substrate scopes and good functional group tolerance.