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Ion-Pair Anchored Protic Ionic Liquids on Magnetic Nano Silica Sulfuric Acid as Efficient Catalysts for Organic Synthesis

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Abstract

The synthesis of pyrazolo[b]phthalazine diones and indazolo[b]phthalazine triones was efficiently achieved using novel magnetically recoverable supported Bronsted acidic ionic liquids. The heterogeneous catalysts were prepared by synthesizing two organosulfonate salts from n-methylimidazole and 1-benzyl-4-phenyl-1H-1,2,3-triazole with 1,4-butanesultone. The organosulfonate zwitterions were non-covalently immobilized onto the previously synthesized nanomagnetic Fe3O4@SiO2–SO3H support to prepare the organometallic hybrid catalysts. Various thermal and spectroscopic techniques, including 1H and 13C NMR, FTIR, SEM, EDX, mapping, XRD, and VSM, were employed to confirm the successful preparation of the novel nanoorganometallic hybrid catalysts. The immobilization of BAILs on the nanoparticles of Fe3O4@SiO2–SO3H facilitated their recycling and improved their thermal stability. This immobilization strategy preserved the flexibility of BAILs, while also allowing for the benefits of both heterogenized and free forms of BAILs. Furthermore, the introduced catalysts demonstrated short reaction times and high yields of products, along with high TON and TOF values, making them superior replacements for previously reported catalysts.

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Acknowledgements

The authors gratefully acknowledge to the Research Council of King Abdulaziz and Yasouj Universities for financial support of this work.

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Gas and Petroleum, Yasouj University, P. O. Box 353, Gachsaran, 75918-74831, Iran

    Mosadegh Keshavarz

  2. Department of Chemistry, College of Sciences, King Abdulaziz University, Jeddah, Saudi Arabia

    Layla A. Taib

  3. Department of Chemistry, Faculty of Science, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran

    Nasir Iravani

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  1. Mosadegh Keshavarz
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  3. Nasir Iravani
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Methodology and experimental by LAT, spectral analysis by Nasir Iravani, supervision and writing by MK.

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Correspondence to Mosadegh Keshavarz.

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Keshavarz, M., Taib, L.A. & Iravani, N. Ion-Pair Anchored Protic Ionic Liquids on Magnetic Nano Silica Sulfuric Acid as Efficient Catalysts for Organic Synthesis. J Inorg Organomet Polym 33, 3247–3258 (2023). https://doi.org/10.1007/s10904-023-02747-0

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