Immobilized N‑Heterocyclic Carbene‑Palladium(II) Complex on Graphene Oxide as Efficient and Recyclable Catalyst for Suzuki–Miyaura Cross‑Coupling and Reduction of Nitroarenes

Abstract

A new and efficient N-heterocyclic carbene (NHC)-palladium(II) complex immobilized on graphene oxide (NHC-Pd@GO) has been successfully designed and synthesized. The prepared NHC-Pd@GO heterogeneous catalyst was fully characterized using a combination of fourier transform infrared spectroscopy (FTIR), inductively coupled plasma-optical emission spectroscopy (ICP-OES), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), thermogravimetric analysis (TGA) and Brunauer–Emmett–Teller surface area analysis (BET). This new air- and moisture-stable NHC-Pd@GO heterogeneous catalytic system was found to be a highly active catalyst in the Suzuki–Miyaura cross-coupling between phenylboronic acid and various aryl halides (bromides/chlorides/iodides) and in the reduction of nitroarenes. These organic transformations were best performed in an aqueous ethanol and aqueous methanol solvent system respectively with low catalyst loading under mild reaction conditions. Furthermore, NHC-Pd@GO heterogeneous catalyst could be recovered easily and reused at least eleven times in Suzuki–Miyaura cross-coupling and nine times in reduction of nitroarenes without any considerable loss of its catalytic activity. The stability and good selectivity of the NHC-Pd@GO heterogeneous catalyst in recycling experiments signify that it could be useful for practical application in various organic transformations.