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A selective heterogeneous cellulose supported Schiff base Cu(II) catalyst for Chan–Evans–Lam coupling

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Abstract

Cellulose-immobilized Cu(II) Schiff base complex [Cell-AP-Cu(II)] has been designed and synthesized by multistep approach by the reaction of Schiff base functionalized cellulose (Cell-AP) with Cu(OAc)2 in ethanol under reflux condition. The [Cell-AP-Cu(II)] complex was characterized by FT-IR, TGA, XRD, SEM, EDS, and BET/BJH techniques. The functionality and composition of the catalyst was confirmed by IR and EDX analysis, respectively. The catalytic effectiveness of [Cell-AP-Cu (II)] is investigated for Chan–Lam coupling of phenylboronic acids and secondary amines. A range of functionalized derivatives have been synthesized with high yield in short reaction time. The plausible mechanism illustrates the formation of derivatives. The peculiar advantages of the proposed protocol are high TONs (up to 873) and TOFs (up to 873), minimal catalyst loading (0.11 mol %), recyclability of the catalyst (up to 5 times) and moderate reaction conditions.

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Acknowledgements

One of the authors, Pharande P. S., is grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, Government of India for the award of the Senior Research Fellowship (File no. 09/816(0044)/2019-EMR-I).

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Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, Maharashtra, 416004, India

    P. S. Pharande, P. M. Mhaldar, G. S. Rashinkar & D. M. Pore

  2. Bharati Vidyapeeth’s Dr. Patangrao Kadam Mahavidyalaya, Sangli, Maharashtra, 416416, India

    T. R. Lohar

  3. Centre for Herbal Pharmacology and Environmental Sustainability, Chettinad Hospital and Research Institute, Kelambakkam, Tamil Nadu, 603103, India

    S. K. Ghotekar

  4. Department of Chemistry, Veer Narmad South Gujarat University, Surat, 395007, India

    Tarulata N. Chhowala

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All authors contributed to design, material preparation, data collection. The first draft of the manuscript was written by P. S. Pharande. All authors read and approved the final manuscript.

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Correspondence to D. M. Pore.

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Pharande, P.S., Mhaldar, P.M., Lohar, T.R. et al. A selective heterogeneous cellulose supported Schiff base Cu(II) catalyst for Chan–Evans–Lam coupling. Res Chem Intermed 49, 4541–4560 (2023). https://doi.org/10.1007/s11164-023-05089-1

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