Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system.J Org Chem. 2013 Apr 05; 78(7):3030-8.JO
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.