Transition Metal-catalyzed Functionalization Of 1-naphthylamine At C-8 Carbon-hydrogen Bond

Direct and selective functionalization of C-H bonds has emerged as one of the most promising and powerful synthetic tool for the formation of C-C bonds.The application of this tactic to the rapid synthesis of bioactive molecules such as natural products and medicinal compounds has garnered significant attention of researchers due to the strategic advantages in terms of great efficiency and economy.In this thesis,our researches have focused on the quinolinamide-directed regioselective C8 arylation of 1-naphthylamines with aryl bromides by the catalysis of Pd?OAc?₂,to offer exclusively 8-aryl-1-naphthylamine derivatives under solvent-free condition.In view of great regioselectivity,compatibility and efficiency of this methodology,we turned our attention to investigate whether the method could also facilitate the C8 alkylation of 1-naphthylamines with non-functionalized alkyl bromides as coupling partners.A practical methodology for the Pd-catalyzed regioselective alkylation of 8-C-H bonds in 1-naphthylamides containing a quinolinamide moiety as a bidentate directing group with functionalized alkyl chlorides is described.Various functionalized alkyl halides including?-chloro alkyl chlorides and benzyl chlorides can be employed as coupling partners,providing exclusively 8-alkyl-1-naphthylamide derivatives.