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N-Arylation of n-octylamine and adamantane-containing amines with iodobenzene and its deriva-tives has been performed in DMSO using copper(I) iodide and copper nanoparticles in the presence of various ligands as catalysts. In all cases, 2-isobutyrylcyclohexanone turned out to be the most efficient ligand, and higher yields of the arylation products were obtained in the presence of copper nanoparticles. The nanocatalyst can be recycled 9 times without significant loss of yield. [ABSTRACT FROM AUTHOR]

A comparative study of the catalytic efficiency of Pd(0) and Cu(I) complexes in the reactions of adamantanamines with fluoro- and trifluoromethyl-substituted 2-bromopyridines was carried out using previously optimized catalytic systems. It was shown that in the absence of steric hindrances in the starting compounds, the copper and palladium catalysts were comparable in efficiency. In some cases, the yields of the target N-heteroarylated compounds in the copper-catalyzed reactions were even higher, which can be explained by the formation of N,N-diheteroarylated by-products under palladium-catalyzed conditions. At the same time, ortho-fluorine- and ortho-trifluoromethyl-substituted 2-bromopyridines successfully react exclusively under palladium catalysis. [ABSTRACT FROM AUTHOR]

The catalytic efficiencies of palladium(0) and copper(I) complexes in the amination of 2-bromopyridine and its fluorine-containing derivatives with (1-adamantyl)methanamine and 2-(1-adamantyloxy)ethanamine were compared. Both types of catalytic systems were shown to be applicable for the preparation of the corresponding N-pyridyl derivatives from 3- and 5-fluoro- and 4-, 5-, and 6-trifluoromethyl-2-bromopyridines. DavePhos was found to be the most efficient ligand in the Pd(0)-catalyzed reactions; however, the reactions with 2-bromo-4-(trifluoromethyl)pyridine and 2-bromo-5-(trifluoromethyl)pyridine were accompanied by formation of a considerable amount of the diarylation product. The diarylation process was significantly suppressed in the presence of copper(I) complexes. [ABSTRACT FROM AUTHOR]