N-arylations of nitrogen-containing heterocycles with aryl and heteroaryl halides using a copper(I) oxide nanoparticle/1,10-phenanthroline catalytic system.

[摘要]：A general procedure for solvent-free N-arylations of nitrogen-contg. heterocycles, i.e. imidazoles, triazoles, and indoles, with aryl and heteroaryl halides catalyzed by copper(I) oxide (Cu2O) nanoparticles is demonstrated. Four types of Cu2O were evaluated: the bulky compd. and its cubic, octahedral, and spherical nanoparticulate forms. The results show that Cu2O nanoparticles, in particular the cubic form, are highly efficient for the N-arylation reaction. In the presence of cubic Cu2O nanoparticles, 1,10-phenanthroline, and tetrabutylammonium fluoride, a variety of nitrogen-contg. heterocycles smoothly underwent N-arylation with aryl and heteroaryl halides at 110-145 癈 to give the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under solvent-free conditions. The reaction mechanism is also discussed.

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