Iron oxide encapsulated by copper-apatite: an efficient magnetic nanocatalyst for N-arylation of imidazole with boronic acid

Abstract

N-Arylation of imidazole with various arylboronic acids was carried out using Fe3O4@Cu-apatite nanocatalyst with good to excellent yields.

Regioselective, Greener Protocol for the Synthesis of N‐Heterocyclic Compounds Catalyzed by Recyclable CuO NPs Coated with Ionic Liquid (CuO[HN222][Al2Cl7]

“…Adsorption and desorption are believed to be the primary mechanism steps for the catalytic process. [34][35][36] The phenylboronic acid was adsorbed onto the CuO of Scheme 3. Substrate scope of imidazole, benzimidazole, and 5, 6-dimethylbenzimidazole with various phenylboronic acids.…”

“…To examine the plausible mechanism of N‐arylation reaction catalyzed by CuO[HN 222 ][Al 2 Cl 7 ], the reaction between adenine and phenylboronic acid was chosen as a model reaction (Scheme 7). Adsorption and desorption are believed to be the primary mechanism steps for the catalytic process [34–36] . The phenylboronic acid was adsorbed onto the CuO of CuO[HN 222 ][Al 2 Cl 7 ] NPs surface in the first stage, forming intermediate‐II.…”

Recent advances in the application of nanocatalysts in C‐N coupling reactions

“…In 2019, Amadine et al [ 121 ] introduced magnetic Fe 3 O 4 @Cu‐apatite to catalyze N ‐arylation of N(H)‐heterocycles (imidazole and indole) with different arylboronic acids. For the preparation of this core‐shell material, first, the Fe 3 O 4 NPs were synthesized through a solvothermal technique and then encapsulated using copper‐apatite.…”

“…Many of these protocols still suffer from several limitations including high temperature, use of toxic solvents, prolonged reaction time, and recyclability of catalyst. [121][122][123][124][125][126][127][128][129][130][131][132] Thus, due to the importance of C-N coupling in medicinal chemistry, the development of novel, green, and efficient catalytic systems is in great demand and has attracted considerable interest.…”

N‐Arylation of Imidazoles: An Overview

“…A highly efficient and reusable Fe 3 O 4 @Cu-apatite nanocatalyst was synthesised for the preparation of N-arylimidazoles from various arylboronic acids. [49] Initial studies showed that coating iron oxide by copper-apatite resulted a better catalytic activity than coating Cu-apatite by Fe 3 O 4 and by screening the effect of solvents and bases, better product yields were obtained for MeOH and K 2 CO 3 respectively. Optimisation studies disclosed that the reaction can be carried out using 15 mol% of nanocatalyst and 1 mmol of K 2 CO 3 in MeOH at 60°C (Scheme 25).…”