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Palladium immobilized onto 1,4-bis(pyrid-4-yl)benzene grafted to n-propyl-functionalized Fe3O4@MCM-41 nanoparticles (PBPBPMF) as a novel, green, reusable, and versatile catalyst for preparing bis(pyrazolyl)methane and biphenyl derivatives

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Abstract

In this research, a novel and efficient nanocatalyst, namely, palladium immobilized onto 1,4-bis(pyrid-4-yl)benzene grafted to n-propyl-functionalized Fe3O4@MCM-41 nanoparticles (PBPBPMF), was synthesized and introduced. Then, its catalytic activity was tested in the synthesis of bis(pyrazolyl)methane (14 examples, 90–97%, 9–25 min, solvent-free, 60 °C) and biphenyl (13 examples, 80–98%, 10–120 min, PEG-400, 70 °C) derivatives. Bis(pyrazolyl)methane derivatives were synthesized via a one-pot pseudo-five-component reaction of aldehydes, ethyl acetoacetate, and phenylhydrazine, and biphenyl derivatives were obtained by a Stille coupling reaction. Transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDS), scanning electron microscopy (SEM), N2 sorption isotherms, vibrating sample magnetometer (VSM), inductively coupled plasma atomic emission spectrometer (ICP-OES), X-ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), and elemental mapping analyses were used to identify the catalyst. The PBPBPMF is a heterogeneous catalyst with several advantages, including a large specific surface area, ease of purification, and separation from the reaction mixture; furthermore, the nanocatalyst was recycled six times without appreciably altering its catalytic properties.

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Acknowledgements

The authors are grateful to acknowledge the Takin Shimi Sepanta Industries Co., Ilam, Iran.

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The authors have no relevant financial or non-financial interests to disclose.

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Contributions

H.A prepared the catalyst. A.R.A optimized Stille reaction and assisting to edit the article. S.V.M optimized the preparation conditions of bis(pyrazolyl)methanes. C.R.B synthesized derivatives 1a-7a. M.K synthesized derivatives 1b-6b. W.R.K synthesized derivatives 7b-13b. D.S.S determined the skeleton of PBPBPMF by SEM, TEM, EDS, and elemental mapping analyses. L.H.S determined the skeleton of PBPBPMF via ICP, VSM, and BET analyses. A.R.A determined the skeleton of PBPBPMF through FT-IR, XRD, and TGA analyses. M.H wrote the article and synthesized derivatives 8a-14a.

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Correspondence to Majid Heidarpour.

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AlMohamadi, H., AlBajalan, A.R., Menon, S.V. et al. Palladium immobilized onto 1,4-bis(pyrid-4-yl)benzene grafted to n-propyl-functionalized Fe3O4@MCM-41 nanoparticles (PBPBPMF) as a novel, green, reusable, and versatile catalyst for preparing bis(pyrazolyl)methane and biphenyl derivatives. Res Chem Intermed (2024). https://doi.org/10.1007/s11164-024-05320-7

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