Palladium-catalyzed aromatic C–H alkylation of 1-naphthylamines with dichloroalkanes and its application in fused polycyclic amine synthesis

Abstract

Herein, we report a palladium-catalyzed aromatic C–H bond alkylation reaction of 1-naphthylamines at the C8 site with dichloroalkanes as alkylating agents. DFT calculation demonstrates the distinctive advantage of the separated dichloroalkanes in the reaction by stabilizing the key intermediate via C–H⋯N or C–H⋯π interaction induced by the additional Cl atom. In addition to the specific alkylation site selectivity in the naphthyl ring, the products provided by the current C–H alkylation protocol display important applications in the construction of fused polycyclic amines via a one-step treatment.