Novel synthesis of a new skeletal compound benzonaphthazepine by regioselective C-H activation utilizing the intramolecular coordination of an amine to Pd

The novel synthesis of a new skeletal compound, benzonaphthazepine, from N-bromobenzylnaphthylamine using a Pd reagent is described. In the biaryl coupling reaction of N-bromobenzylnaphthylamine using a Pd reagent, the intramolecular coordination of the benzylamino group to Pd causes regioselective C-H activation at the peri position relative to the amine group on the naphthalene ring, producing benzonaphthazepine in good to excellent yield. The bulkiness of the substituent at C₇ on the naphthalene ring affects the regioselectivity of the biaryl coupling reaction.