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

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.