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

作者：Tang, Bo Xiao; Guo, Sheng Mei; Zhang, Man Bo; Li, Jin Heng^*

来源：Synthesis (Germany), 2008, 2008(11): 1707-1716.

DOI：10.1055/s-2008-1067014

• copper(I) oxide nanoparticles
• 1,10-phenanthroline
• N-arylations
• heterocycles
• halides

A general procedure for solvent-free N-arylations of nitrogen-containing 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 compound 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-containing heterocycles smoothly underwent N-arylation with aryl and heteroaryl halides at 110-145 degrees C 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.

• 出版日期2008-6-2
• 单位湖南师范大学