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Synthesis of a new complex of lanthanum on MCM-41 as an efficient and reusable heterogeneous catalyst for the chemoselective synthesis of sulfoxides and tetrahydrobenzo[b]pyrans

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Abstract

In this project, the l-arginine salen Schiff-base (ASS) complex of lanthanum on the functionalized surface of mesoporous MCM-41 (MCM-41@ASS-La) was synthesized for the first time. To prepare MCM-41@ASS-La, the surface of MCM-41 was modified with 3-iodopropyl trimethoxysilane (IPTMS) and then l-arginine salen Schiff-base ligand anchored om modified MCM-41. Then, lanthanum ions were stabilized on its surface. Then, MCM-41@ASS-La was characterized by different techniques e.g. Fourier transform infrared spectroscopy (FTIR), energy-dispersive X-ray Spectroscopy (EDX), scanning electron microscopy (SEM), wavelength dispersive X-ray spectroscopy (WDX), energy-dispersive X-ray spectroscopy (EDS), inductively coupled plasma atomic emission spectroscopy (ICP-AES), and N2 adsorption–desorption isotherms. Next step, the synthesized MCM-41@ASS-La was investigated as an efficient and reusable nanocatalyst for the chemoselective synthesis of sulfoxides and tetrahydrobenzo[b]pyrans. In these studies, the reaction conditions for the synthesis of tetrahydrobenzo[b]pyrans were optimized, and the best results were obtained in H2O as an ideal, available and, green solvent in the presence of MCM-41@ASS-La nanocatalyst. Also, the reaction conditions for the oxidation of sulfides to sulfoxides were optimized, and the best results were obtained under solvent-free conditions using hydrogen peroxide (H2O2) in the presence of MCM-41@ASS-La nanocatalyst. Then, several derivatives of sulfoxides and tetrahydrobenzo[b]pyrans were synthesized in the presence of MCM-41@ASS-La nanocatalyst under optimized conditions. In addition, MCM-41@ASS-La nanocatalyst can be recovered (about 96%) and reused for several cycles without metal leaching or reactivation.

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Acknowledgements

Authors thank the research facilities of Ilam University for fiscal assistance of this work.

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This research received no specific grant from any funding agency in the public, commercial, or not-for-profit sectors. This work was not supported by any funding.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ilam University, 69315516, Ilam, Iran

    Mohsen Nikoorazm, Bahman Tahmasbi, Mitra Darabi, Yunes Abbasi Tyula, Shahab Gholami, Maryam Khanmoradi & Mostafa Koolivand

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  1. Mohsen Nikoorazm
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  2. Bahman Tahmasbi
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  3. Mitra Darabi
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Contributions

MN: supervision. BT: supervision, writing review and editing. MD: data collection, Methodology. YAT: methodology.  SG: methodology. MK: writing—original draft. MK: methodology.

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Correspondence to Mohsen Nikoorazm or Bahman Tahmasbi.

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Nikoorazm, M., Tahmasbi, B., Darabi, M. et al. Synthesis of a new complex of lanthanum on MCM-41 as an efficient and reusable heterogeneous catalyst for the chemoselective synthesis of sulfoxides and tetrahydrobenzo[b]pyrans. J Porous Mater 31, 511–526 (2024). https://doi.org/10.1007/s10934-023-01530-3

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