Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides with Alkyl Halides via Bidentate-Chelation Assistance

A Pd-catalyzed regioselective alkylation of C8–H bonds in 1-naphthylamides containing a quinolinamide or picolinamide moiety as a bidentate directing group with alkyl halides is reported. The amide directing group can be easily hydrolyzed under basic conditions. Various alkyl halides including alkyl iodides and benzyl bromide or chloride can be employed as coupling partners, exclusively providing 8-alkyl-1-naphthylamide derivatives.