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 %).

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N,N'-bis(bromobenzyl) substituted diazacrown ethers were obtained in the reactions of corresponding free diazacrowns with two equivalents of bromobenzyl bromides in high yields. These compounds were introduced in the Pdcatalyzed amination reaction with 1,3-bis(aminomethyl) and 1,3-bis(2-aminoethyl)adamantanes to give macrobicyclic products. The yields were shown to be dependent on the nature of starting diazacrown derivatives and diamines. N,N'-bis(3-bromobenzyl)

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N , N' -bis(bromobenzyl) and N , N' -bis(halopyridinyl) derivatives of diaza-12-crown-4, diaza-15-crown-5 and diaza-18-crown-6 ethers were synthesized in high yields. The Pd-catalyzed macrocyclization reactions of these compounds were carried out using a variety of polyamines and oxadiamines were carried out to give novel macrobicyclic and macrotricyclic compounds of the cryptand type. The dependence of the yields of macropolycycles on the nature of the starting diazacrown derivatives and polyamines was established. Generally N,N' -bis(3-bromobenzyl)-substituted diazacrown ethers and oxadiamines provided better yields of the target products. The highest yield of the macrobicyclic products reached 57%.