F+ Reagent-Promoted Pd-Catalyzed C7–H Arylation of 1-Naphthamides

Abstract

The development of a strategy for remote C7–H functionalizations of the naphthalene rings is greatly challenging. Disclosed herein is an example of direct and regioselective arylation of the naphthalene rings at the C7 position that is promoted by F+ reagents. This protocol features good tolerance of reactive functional groups, mild reaction conditions, and simple reaction system. By control experiments, a kinetic isotope effect (KIE) experiment, and NMR experiments, the mechanistic pathway involving a carbopalladation/aryl migration has been illustrated clearly. Beyond the simple directing function, the sterically hindered N-(t-butyl)amide plays an important role in the regioselectivity control via a carbopalladation/aryl migration.