Metallation of benzylic amines via amine-borane complexes

Article abstract of DOI:10.1016/S0040-4020(98)00783-2

Formation of borane complexes of N,N-dimethylbenzylamine, N,N- dimethyl(1-naphthyl)methylamine, N,N-dimethyl(2-naphthyl)methylamine, N- methyltetrahydroisoquinoline and N-methylisoindoline facilitates regioselective metallation of these systems using BuLi, giving intermediate benzylic anions which react with a range of electrophiles to give products in good yield.