In situ green synthesis of Cu‐Ni bimetallic nanoparticles supported on reduced graphene oxide as an effective and recyclable catalyst for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles

Abstract

In the present work, for the first time we have designed a novel approach for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles using reduced graphene oxide (rGO) decorated with Cu‐Ni bimetallic nanoparticles (NPs). In situ synthesis of Cu/Ni/rGO nanocomposite was performed by a cost efficient, surfactant‐free and environmentally benign method using Crataegus azarolus var. aronia L. leaf extract as a stabilizing and reducing agent. Phytochemicals present in the extract can be used to reduce Cu2+ and Ni2+ ions and GO to Cu NPs, Ni NPs and rGO, respectively. Analyses by means of FT‐IR, UV–Vis, EDS, TEM, FESEM, XRD and elemental mapping confirmed the Cu/Ni/rGO formation and also FT‐IR, NMR, and mass spectroscopy as well as elemental analysis were used to characterize the tetrazoles. The Cu/Ni/rGO nanocomposite showed the superior catalytic activity for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles within a short reaction time and high yields. Furthermore, this protocol eliminates the need to handle HN3.

Curcuma longa Mediated Synthesis of Copper Oxide, Nickel Oxide and Cu-Ni Bimetallic Hybrid Nanoparticles: Characterization and Evaluation for Antimicrobial, Anti-Parasitic and Cytotoxic Potentials

“…Metallic nanoparticles were synthesized using C. longa extract as a capping and reducing agent. When the reaction was carried out between C. longa and respective salts, the color of the mixture changed from dark brown to black and dark gray, which confirmed the biosynthesis of CuO-NPs, NiO-NPs, and Cu-Ni alloy NPs [46][47][48]. The reaction mixture was centrifuged and stored for physiochemical characterization [49].…”

Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

“…They have also been used in agrochemicals, as ligands in coordination chemistry, and in materials science. [26] Numerous methods have been developed for the synthesis of tetrazoles, [20,27,28] they have been generally synthesized by [3 + 2]-cycloaddition reaction between nitriles and azides in the presence of various transition metal catalysts, such as Pd, [20,28,29] Ni, [22,30,31] and iron compounds. [32][33][34] Methods for the synthesis of 5-substituted 1H-tetrazoles from aldoximes or aldehydes in the presence of copper (II) catalysts have also been reported.…”

Carbon–nitrogen bond formation using modified graphene oxide derivatives decorated with copper complexes and nanoparticles

“…[ 91 ] Due to the outstanding characteristics of bimetallic NPs such as higher catalytic properties than monometallic ones, reducibility, and synergistic properties, the use of Cu–Ni bimetallic NPs supported on reduced graphene oxide (Cu/Ni/rGO nanocomposite) as an efficient catalyst was investigated for the synthesis of tetrazole derivatives through the reaction of N ‐benzyl‐ N ‐arylcyanamides with sodium azide (Scheme 33). [ 92 ] Reducing the tendency of agglomeration of Cu and Ni NPs by rGO in the nanocomposite permitted to achieve high performance for this reaction. N ‐Benzyl‐ N ‐arylcyanamides with both electron‐donating and electron‐withdrawing groups produced the corresponding products under thermal conditions in high yields (81%–89%) after 130–190 min.…”

“…FESEM images of (a) fresh and (b) recycled Cu/Ni/rGO nanocomposite (Reproduced from ref. [ 92 ] with permission from John Wiley and Sons)…”