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N-(Het)arylation of adamantane-containing amines with halonaphthalenes and haloquinolines catalyzed by either CuI or copper nanoparticles with an average size of 25 nm in the presence of 2-isobutyrylcyclohexanone, rac-BINOL, and l-proline as a ligand and Cs2CO3 as a base in DMSO at 110 °C was studied. The reactions proceed smoothly with 2-iodonaphthalene and 6-iodoquinoline, the possibility of successful reactions with 6- and 3-bromoquinolines was also shown. In the case of 1-bromonaphthalene, 5- and 8-bromoquinolines, only Pd-catalyzed amination can provide the high yields of the products. An alternative possibility of C(sp2)—N bond formation was studied employing the Chan—Lam reaction with of 2-naphthaleneboronic acid and pinacolates of 6- and 3-quinolineboronic acids. [ABSTRACT FROM AUTHOR]