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Three-component coupling of boronic acids, amines, and carbon disulfide by a heterogeneous catalyst of copper (II) embedded in a highly porous and magnetic Schiff base network of melamine

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Abstract

In this work, the mesoporous magnetic heterogeneous catalyst was synthesized by anchoring copper (II) onto the nitrogen-rich poly (melamine) Schiff base networks magnetic nanocomposite. First, MNP (Fe3O4@SiO2) was functionalized with chlorosilane (CPTS). Then, the chlorine of these functionalized magnetic nanoparticles could react with the –NH2 groups of the melamine through a nucleophilic substitution reaction. Simultaneously, the condensation polymerization of melamine and benzene-1, 3, 5-tricarbaldehyde was carried out in the presence of surface-modified magnetic nanoparticles. Later, Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), scanning electron microscopy (SEM), atomic absorption spectroscopy (AAS), Brunauer–Emmett–Teller surface analysis (BET), and energy dispersive analysis were deployed to characterize the catalyst. The results of the AAS measurement showed that the copper ion loading on the mesoporous nitrogen-rich supported catalyst was about 0.82 mmol g−1. The synthesized nanocomposite was used as a catalyst and shows excellent activity in the three-component coupling reaction of amines, carbon disulfide, and boronic acids. In the presence of 70 mg of the catalyst, a wide range of functionalized dithiocarbamates were synthesized leading to excellent yields. Moreover, this MNP@SNWMe@Cu catalyst was easily recovered and reused seven times without significant loss of its activity. The results of this research exhibited that the synthesized catalyst functioned with high catalytic activity in this reaction.

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Authors and Affiliations

  1. Department of Chemistry, Sharif University of Technology, Tehran, Iran

    Nahid Keshavarzi, Mohammad Kohestanian & Ali Pourjavadi

  2. Biomedical Engineering Department, Polymer Faculty, Meybod University, Meybod, Yazd, Iran

    Alireza Sabzevari

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  1. Nahid Keshavarzi
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  2. Mohammad Kohestanian
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  3. Alireza Sabzevari
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  4. Ali Pourjavadi
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Prof. AP: project administration, supervision, resources, review & editing, funding acquisition, and validation. NK and MK: conceptualization, investigation, methodology, validation, formal analysis, writing-original draft, and funding acquisition. AS: methodology, validation, and formal analysis.

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Correspondence to Nahid Keshavarzi or Ali Pourjavadi.

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Keshavarzi, N., Kohestanian, M., Sabzevari, A. et al. Three-component coupling of boronic acids, amines, and carbon disulfide by a heterogeneous catalyst of copper (II) embedded in a highly porous and magnetic Schiff base network of melamine. Res Chem Intermed 49, 4423–4441 (2023). https://doi.org/10.1007/s11164-023-05081-9

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