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Cellulose/silica supported Schiff base Pd(II) catalyst for copper-free Sonogashira cross-coupling

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Abstract

In present investigation, a cellulose/silica supported Schiff base Pd(II) catalyst, acronym as Cell/SiO2-Sal-Pd(II), has been designed and synthesized using cellulose as support. The catalyst was comprehensively characterized by advanced techniques such as FTIR, XRD, TGA, SEM, EDS, and BET/BJH. From the EDX analysis, the loading of palladium found to be 0.017 mol%. TEM analysis revealed ~ 70 nm particle size of the catalyst. The catalytic efficiency of Cell/SiO2-Sal-Pd(II) was thoroughly scrutinized in the context of the Sonogashira cross-coupling. Varity of functionalized diary acetylene derivatives have been achieved with admirable yields from coupling of aryl halides and phenyl acetylenes. The XRD, SEM and TGA analysis of recycled catalyst revealed remarkable catalytic activity. The proposed approach exhibits remarkable merits such as impressively low catalyst loading (0.009 mol%), elevated turnover numbers (up to 10,556), commendable turnover frequencies (up to 3519), exceptional thermal stability (up to 356.75 °C), high surface area (94.825 m2/g), superior catalyst reusability (up to 5 times) and the employment of an environmentally friendly aqueous acetonitrile solvent system.

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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

    Pravin S. Pharande, Mayuri V. Patil, Suraj A. Sonawane & Dattaprasad M. Pore

  2. Department of Chemistry, Shreemant Bhaiyyasaheb Rajemane Mahavidyalaya, Mhaswad, Satara, Maharashtra, 415509, India

    Pradeep M. Mhaldar

  3. Department of Chemistry, Tuljaram Chaturchand College Baramati, Maharashtra, 413102, India

    Shrikrishna T. Salunke

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  1. Pravin S. Pharande
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by P. S. Pharande and P. M. Mhaldar. The first draft of the manuscript was written by D. M. Pore and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Dattaprasad M. Pore.

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Pharande, P.S., Mhaldar, P.M., Patil, M.V. et al. Cellulose/silica supported Schiff base Pd(II) catalyst for copper-free Sonogashira cross-coupling. Res Chem Intermed 50, 551–573 (2024). https://doi.org/10.1007/s11164-023-05186-1

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