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CuI Immobilized on Tricationic Ionic Liquid Anchored on Functionalized Magnetic Hydrotalcite (Fe3O4/HT-TIL-CuI) as a Novel, Magnetic and Efficient Nanocatalyst for Ullmann-Type C–N Coupling Reaction

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Abstract

One of the most important reactions in organic synthesis is Ullmann-type C–N coupling reaction which has been used for preparation of numerous biologically active compounds. In this work, CuI immobilized on tricationic ionic liquid anchored on functionalized magnetic hydrotalcite (Fe3O4/HT-TIL-CuI) has been successfully prepared and fully characterized by different techniques, including fourier-transform infrared spectroscopy, vibrating sample magnetometer, thermo gravimetric analysis, transmission electron microscopy, field-emission scanning electron microscopy, energy dispersive X-ray spectroscopy, elemental mapping, zeta potential, X-ray diffraction, temperature programmed desorption of ammonia (NH3-TPD), temperature-programmed reduction and inductively coupled plasma. The results showed that the as-prepared nanocatalyst possesses plate-like morphology with approximate size of 50 nm and superparamagnetic behavior. Also, total acidity and total hydrogen consumption of the nanocatalyst were measured to be 8.5 and 1.41 mmol g−1, respectively. This nanocatalyst exhibited favorable performance for C–N coupling reaction among a variety of aryl halides and N(H)-heterocycles (benzimidazoles, pyrazoles and triazoles) in the presence of 2.5 mol% of nanocatalyst without any additives under air atmosphere revealing high yields in all cases. Besides, it is noted that in the present system the desired product can be easily and quickly isolated and nanocatalyst also recovered magnetically from the reaction mixture employing a permanent magnet for at least six consecutive trials without a discernible decrease in catalytic activity which makes the proposed methodology appropriate for industrial. The findings demonstrated the advantages of the present method as no need for neutral atmosphere, appropriate times, recyclability of the catalyst, broad substrate scope, minimization of chemical waste, simple purification of products, easy workup process, and high yields.

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Acknowledgements

We gratefully acknowledge the support of this work by the Shiraz University of Technology Research Council.

Funding

This work was supported by the Shiraz University of Technology Research Council.

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Authors and Affiliations

  1. Department of Chemistry, Shiraz University of Technology, 71555-313, Shiraz, Iran

    Maryam Rajabzadeh, Zeinab Zarei & Reza Khalifeh

  2. Department of Chemistry, Kazerun Branch, Islamic Azad University, Kazerun, Iran

    Nahid Najdi

Authors
  1. Maryam Rajabzadeh
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  2. Nahid Najdi
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  3. Zeinab Zarei
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  4. Reza Khalifeh
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Contributions

MR: Investigation, material preparation, data collection and analysis. NN: Investigation, Material preparation. ZZ: Writing—review & editing. RK: Conceptualization, supervision, project administration, review & editing. All authors read and approved the final manuscript.

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Correspondence to Maryam Rajabzadeh or Reza Khalifeh.

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Rajabzadeh, M., Najdi, N., Zarei, Z. et al. CuI Immobilized on Tricationic Ionic Liquid Anchored on Functionalized Magnetic Hydrotalcite (Fe3O4/HT-TIL-CuI) as a Novel, Magnetic and Efficient Nanocatalyst for Ullmann-Type C–N Coupling Reaction. J Inorg Organomet Polym 32, 2696–2711 (2022). https://doi.org/10.1007/s10904-022-02316-x

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