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Novel ferrocene-based ionic liquid supported on silica nanoparticles as efficient catalyst for synthesis of naphthopyran derivatives

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Abstract

We report synthesis of silica nanospheres containing ferrocene-tagged imidazolium acetate (SiO2@Im-Fc[OAc]) as efficient heterogeneous nanocatalyst for synthesis of naphthopyran derivatives under solvent-free conditions, based on modification of nano SiO2 by ionic liquid with ferrocene tags and subsequent anion metathesis reaction. The synthesized novel nanocatalyst (SiO2@Im-Fc[OAc]) was systematically characterized using Fourier-transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction analysis, and field-emission scanning electron microscopy. The catalytic activity of (SiO2@Im-Fc[OAc]) was tested in one-pot three-component reaction of aromatic aldehydes, malononitrile, and 2-naphthol for facile synthesis of naphthopyran derivatives. To achieve high catalytic efficacy, the effects of various reaction parameters such as temperature, amount of catalyst, type of solvent, etc. were investigated. Furthermore, recovery and reuse of the nanocatalyst several times was demonstrated without appreciable loss in catalytic activity. The presented protocol offers several advantages, including green and ecofriendly nature, operational simplicity, higher yield, and easy recovery and reuse of the nanostructured catalyst. The workup of these very clean reactions involves only recrystallization of the product from ethanol and recovery of the catalyst by filtration.

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Acknowledgements

The authors thank research affairs of the University of Tabriz for financial support.

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Authors and Affiliations

  1. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, P.O. Box 51666-16471, Iran

    Reza Teimuri-Mofrad, Mahdi Gholamhosseini-Nazari, Elmira Payami & Somayeh Esmati

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  1. Reza Teimuri-Mofrad
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  2. Mahdi Gholamhosseini-Nazari
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  3. Elmira Payami
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  4. Somayeh Esmati
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Correspondence to Reza Teimuri-Mofrad.

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Teimuri-Mofrad, R., Gholamhosseini-Nazari, M., Payami, E. et al. Novel ferrocene-based ionic liquid supported on silica nanoparticles as efficient catalyst for synthesis of naphthopyran derivatives. Res Chem Intermed 43, 7105–7118 (2017). https://doi.org/10.1007/s11164-017-3061-x

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  • DOI: https://doi.org/10.1007/s11164-017-3061-x

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