The catalytic activity of copper nanostructures in the condensation reaction of selected indoles and aldehydes or ketones was investigated. Cu(acac) 2 , zeolite Y-encapsulated Cu(acac) 2 , free and zeolite Y-encapsulated CuO nanoparticles, and Cu 2 O nanoparticles with different size and shapes were prepared successfully and characterized by means of UV-Vis spectroscopy, Fourier-transform infrared spectroscopy (FTIR), diffuse reflectance spectroscopy (DRS), X-Ray diffraction analysis (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), and energy dispersive X-Ray analysis (EDX). Cubic Cu 2 O nanoparticles showed superior activity as a heterogeneous catalyst compared to other catalytic systems. Excellent yields of the desired bis(indolyl)methanes were obtained via condensation reaction of indoles and aldehydes in presence of cubic Cu 2 O nanoparticles under mild reaction conditions and the catalyst retained activity for six successive catalytic runs.