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Vanadium–Schiff base complex-functionalized SBA-15 as a heterogeneous catalyst: synthesis, characterization and application in pharmaceutical sulfoxidation of sulfids

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Abstract

VO2(picolinichydrazone) complex as a catalyst was stabilized on a SBA-15 mesoporous silica as a catalytic support by using (3-chloropropyl)triethoxysilane as a connector. SBA-15 is nanoporous and has a high ratio of surface area to volume. The immobilization of a metal–Schiff base complex to the surface area of SBA-15 can improve its catalytic effects by increasing the catalytic surface area. Unlike homogeneous catalysts, heterogeneous catalysts can be recovered and reused several times without any significant loss of catalytic activity. A vanadium–Schiff base complex-functionalized SBA-15 was synthesized by covalency connected by a pre-synthesised VO2(picolinichydrazone) complex to silanated SBA-15. The synthesized vanadium–Schiff base complex was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, carbon nuclear magnetic resonance (13C NMR) spectroscopy and Fourier transform infrared spectroscopy (FT-IR), and the final V/SBA-15 was characterized by FT-IR, ultraviolet–visible spectrophotometry and X-ray powder diffraction. The morphology of V/SBA-15 was also obtained by scanning electron microscopy and transmission electron microscopy. The catalytic effect was examined by using V/SBA-15 as a heterogeneous catalyst in sulfoxidation reactions. The synthesis of modafinil and modafinic acid by pharmaceutical sulfoxidation of solfides was carried out and the effects of different solvents, reaction times and also recoverability and reusability of the heterogeneous catalyst were investigated. This catalyst showed high yield of sulfide conversion, stability and recyclability in the sulfoxidation of sulfides .

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Authors and Affiliations

  1. Department of Chemistry, School of Basic-Science, University of Imam Hossein, Tehran, Iran

    Mohammad Javad Taghizadeh

  2. Department of Chemistry, Sharif University of Technology, Tehran, Iran

    Homman Karimi

  3. Department of Stem Cells and Developmental Biology at Cell Science Research Center, Royan Institute for Stem Cell Biology and Technology, ACECR, Tehran, Iran

    Hamid Sadeghi Abandansari

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  1. Mohammad Javad Taghizadeh
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Correspondence to Mohammad Javad Taghizadeh.

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Taghizadeh, M.J., Karimi, H. & Abandansari, H.S. Vanadium–Schiff base complex-functionalized SBA-15 as a heterogeneous catalyst: synthesis, characterization and application in pharmaceutical sulfoxidation of sulfids. Res Chem Intermed 42, 8201–8215 (2016). https://doi.org/10.1007/s11164-016-2589-5

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