Palladium catalyzed N, N-diarylation of amines in the synthesis of macrocycles with naphthalene and biphenyl fragments

Pd(0)-catalyzed N,N-diarylation of [2-(1-adamantyloxy)ethyl]amine and (2-methoxyethyl)amine with 2,7-dibromonaphthalene and 4,4′-dibromobiphenyl was studied. The diarylated derivatives synthesized were involved in the catalytic macrocyclization with oxadiamines and tetraamine to give macrocycles containing one polyamine fragment in the case of naphthalene-containing derivatives and two polyamine moieties in the case of biphenyl-containing derivative. The yields of the products were found to depend on the structure of the starting compounds.