Novel Synthesis of a New Skeletal Compound Benzonaphthazepine by Regioselective C-H Activation Utilizing the Intramolecular Coordination of an Amine to Pd

Abstract

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.

Key Words

C-H activation - heterocycles - palladium - regioselectivity - coordination

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8

The coupling reaction of 5a using Pd₂(dba)₃ (0.2 equiv) in degassed DMF gave no product and this was accompanied by decomposition of the starting material.