Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System

A palladium­(II)-catalyzed
quinolinamide-directed 8-arylation of
1-naphthylamides with aryl iodides is reported. The bidentate directing
group (quinolinamide) proved to be crucial for a highly regioselective
transformation. In addition, the amide directing group can be easily
hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine
derivatives. The theoretical calculations suggest that the C–H
arylation reaction proceeds through a sequential C–H activation/oxidative
addition pathway.