C-Arylation reactions catalyzed by CuO-nanoparticles under ligand free conditions

Abstract

CuO-nanoparticles were found to be an excellent heterogeneous catalyst for C-arylation of active methylene compounds using various aryl halides. The products were obtained in good to excellent yield. The catalyst can be recovered and reused for four cycles with almost no loss in activity.

Keywords: C-arylation; active methylene compounds; heterogeneous catalyst; recyclability.

Scheme 1

Synthesis of 3-phenylpentane-2,4-dione using CuO-nanoparticles.

Figure 1

Powder X-ray diffraction pattern and TEM image of nano CuO (fresh).

Scheme 2

Synthesis of 3-phenylpentane-2,4-dione using CuO-nanoparticles.

Scheme 3

Synthesis of diethyl 2-aryl-malonate using CuO-nanoparticles.

Figure 2

Proposed reaction pathway for the CuO-nanoparticles catalyzed C–C coupling reaction.

Figure 3

Powder X-ray diffraction pattern and TEM image of recycled CuO-nanoparticles.