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

Catalysis Letters volume 150, pages 384–403 (2020)Cite this article

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.

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Acknowledgements

The authors thank DST-SERB, India (YSS/2015/000010), DST-Nanomission, India (SR/NM/NS-20/2014), and Jain University, India for financial support.

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Author notes

  1. Vishal Kandathil and Bhakti Kulkarni have contributed equally.

Authors and Affiliations

  1. Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Kanakapura, Ramanagaram, Bangalore, Karnataka, 562112, India

    Vishal Kandathil, Bhakti Kulkarni, Aisha Siddiqa, Manjunatha Kempasiddaiah & Siddappa A. Patil

  2. Organic Chemistry Section, Chemical Sciences & Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, Kerala, 695019, India

    B. S. Sasidhar

  3. Pharmaceutical Sciences Department, College of Pharmacy, Rosalind Franklin University of Medicine and Science, 3333 Green Bay Road, North Chicago, IL, 60064, USA

    Shivaputra A. Patil

Authors
  1. Vishal Kandathil
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  2. Bhakti Kulkarni
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  3. Aisha Siddiqa
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  4. Manjunatha Kempasiddaiah
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Correspondence to Siddappa A. Patil.

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Kandathil, V., Kulkarni, B., Siddiqa, A. et al. Immobilized N-Heterocyclic Carbene-Palladium(II) Complex on Graphene Oxide as Efficient and Recyclable Catalyst for Suzuki–Miyaura Cross-Coupling and Reduction of Nitroarenes. Catal Lett 150, 384–403 (2020). https://doi.org/10.1007/s10562-019-03083-0

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Keywords

  • Graphene oxide
  • N-heterocyclic carbene-palladium(II)
  • Heterogeneous catalysis
  • Suzuki–Miyaura cross-coupling
  • Nitroarene reduction