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Heterogenization of Homogeneous Catalyst: An Improved Strategy for an Efficient Synthesis of Highly Substituted 4H-Pyran Scaffolds in Aqueous Based Media

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Abstract

The immobilization of homogeneous catalytic material over suitable heterogeneous support is amongst the recent strategies to minimize the shortcomings and unite the merits of homogeneous and heterogeneous catalysts. However, the physisorption-based immobilization does not serve the purpose because of its temperature as well as solvent dependent highly reversible nature. In the present work, a new catalytic material silica bonded bis(hydrogensulphato)benzene (SiO2-BHSB) was developed through the chemisorption of benzene-1,3-disulfonic acid as an active catalytic material over the surface of micro-sized silica. The synthesis, structure, purity, thermal stability and acid strength of the newly synthesized catalytic material were confirmed by appropriate analytical techniques such as solid-state CP-MAS 13C-NMR, CP-MAS 29Si-NMR, FT-IR, EDX, TGA, DSC and volumetric studies. An efficient and environmentally benign catalytic protocol for the synthesis of highly substituted 4H-pyran scaffolds was developed, in which a small amount of SiO2-BHSB (3 mol%) was observed sufficient to promote a tandem reaction between alkyl acetoacetate, malononitrile and structurally diverse aldehydes to offer good to excellent yields of 4H-pyran derivatives in aqueous based solvent. Structures of the synthesized 4H-pyran derivatives were confirmed by suitable characterization techniques. The catalytic material was observed to have enough catalytic potential to exhibit sustained catalytic activity even after five cycles of its reuse. Features such as presence of two -SO3H groups, strong acidic character, organo–inorganic hybrid nature, highly stable and chemically inert silica base, high heat of adsorption, large surface area and effective pore volume make SiO2-BHSB a versatile and convenient catalytic material. Herein described catalytic protocol stood better in terms of convenient recovery and reuse of catalyst, waste minimization, environment safety, aqueous based solvent, normal energy conditions and operational simplicity than majority of the cited protocols.

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Acknowledgements

We offer this article as our deep sense of homage to our recently departed, highly respected late Professor Dr. V. T. Kamble Sir, (Head, Department of Chemistry, Government Institute of Science, Nagpur, Maharashtra, India). His everlasting blessings and support to our research group will be remembered forever.

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Authors and Affiliations

  1. School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapure University, Solapur, Maharashtra, 413255, India

    S. N. Shringare

  2. Department of Chemistry and Research Center, Padmashri Vikhe Patil College, Pravaranagar, Ahmednagar, Maharashtra, 413713, India

    K. R. Kadam, G. R. Pandhare & V. D. Murade

  3. Department of Chemistry, ACS College Satral, Ahmednagar, Maharashtra, 413711, India

    A. S. Waghmare

  4. Department of Environmental Science, Central University of Rajasthan, Ajmer, Rajasthan, 305817, India

    P. N. Kamble

  5. Department of Chemistry, Waghire College, Saswad, Pune, Maharashtra, India

    N. R. Kamble

  6. School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded, Maharashtra, 431 606, India

    D. S. Wankhede

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Authors have contributed their share in bringing this work in its present form. All the authors have read the manuscript thoroughly and approved it for submission. Details of author’s contributions is as bellow. Conceptualization and coordination: DSW and KRK; experimental: KRK, SNS, and ASW; materials and resources: GRP, and VDM; characterization and analysis: ASW, and NRK; writing and communication: DSW and KRK.

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Shringare, S.N., Kadam, K.R., Pandhare, G.R. et al. Heterogenization of Homogeneous Catalyst: An Improved Strategy for an Efficient Synthesis of Highly Substituted 4H-Pyran Scaffolds in Aqueous Based Media. Catal Lett 154, 1993–2007 (2024). https://doi.org/10.1007/s10562-023-04455-3

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