Copper-catalyzed arylation of oxadiamines and polyamines

Copper-catalyzed arylation of oxadiamines and polyamines aimed at the synthesis of N,N′-diaryl derivatives using bromo- and iodoarenes was studied. Conversion of the starting compounds, selectivity of the arylation of primary amino groups in the presence of the secondary amino groups, and the yields of target products were shown to be strongly dependent on the nature of the oxadiamines and polyamines, aryl halides, and halogen atom, as well as on reaction conditions such as ligand, solvent, and base applied. Reliable catalytic systems were found for each type of starting amine and aryl halide affording the highest possible yields of the products of N,N′-diarylation (65–96 %).