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Synthesis and characterization of Fe3O4@SiO2–polymer-imid–Pd magnetic porous nanospheres and their application as a novel recyclable catalyst for Sonogashira–Hagihara coupling reactions

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Abstract

We demonstrate herein the modification of magnetic nanoparticles and their use as a magnetic nanocatalyst in direct coupling reactions of aryl halides with terminal alkynes. Magnetite particles were prepared by simple co-precipitation method in aqueous medium, and then Fe3O4@ SiO2 nanosphere was synthesized by using nano-Fe3O4 as the core, TEOS as the silica source and PVA as the surfactant. Fe3O4@SiO2 was coated with polymeric N-heterocyclic carbene/Pd. The samples were characterized by X-ray diffraction, Fourier transform infrared spectroscopy, transmission electron microscopy, field emission scanning electron microscopy, dynamic light scattering, thermogravimetric analysis, vibration sample magnetometer and N2 adsorption–desorption isotherm analysis. Poly (N-vinyl imidazole) functionalized Fe3O4@SiO2 nanoparticle was found to be an efficient nanocatalyst in Sonogashira–Hagihara cross-coupling reactions. The nanocatalyst can be easily recovered by a magnetic field and reused for six runs without appreciable loss of its catalytic activity.

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Acknowledgments

The authors are grateful to the council of Iran National Science Foundation and University of Shiraz for their unending effort to provide financial support to undertake this work.

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Authors and Affiliations

  1. Chemistry Department, College of Science, Shiraz University, Shiraz, Iran

    Esmaeilpour Mohsen & Nowroozi Dodeji Fatemeh

  2. Department of Pharmaceutics, School of Pharmacy, Shaheed Beheshti University of Medical Sciences, Tehran, Iran

    Javidi Jaber

  3. Department of Chemistry, Isfahan University of Technology, Isfahan, Iran

    Mokhtari Abarghoui Mehdi

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  1. Esmaeilpour Mohsen
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  2. Javidi Jaber
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  3. Mokhtari Abarghoui Mehdi
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  4. Nowroozi Dodeji Fatemeh
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Correspondence to Javidi Jaber.

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Mohsen, E., Jaber, J., Mehdi, M.A. et al. Synthesis and characterization of Fe3O4@SiO2–polymer-imid–Pd magnetic porous nanospheres and their application as a novel recyclable catalyst for Sonogashira–Hagihara coupling reactions. J IRAN CHEM SOC 11, 499–510 (2014). https://doi.org/10.1007/s13738-013-0323-4

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