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A novel dinuclear schiff base copper complex as an efficient and cost effective catalyst for oxidation of alcohol: Synthesis, crystal structure and theoretical studies

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Abstract

An environmentally friendly protocol is described for an economic, practical laboratory-scale oxidation of primary and secondary alcohols to aldehydes and ketones, using a bis-chloro-bridged binuclear Cu(II) complex [(HL)Cu(μ 2-Cl)2Cu(HL)]*1.5 CH3OH as catalyst. The catalyst was prepared in situ from commercially available reagents and is characterized by single crystal X-ray analysis, FT-IR, UV-visible spectra, mass spectrometry, and powder x-ray diffraction (PXRD). The geometry of the complex has been optimized using the B3LYP level of theory confirming the experimental data. Our results demonstrated well the efficiency, selectivity and stability of this new catalyst in the oxidation of alcohols in ethanol and tert-butyl hydroperoxide (tBuOOH) as a green solvent and oxidant, respectively. Turnover number and reusability have proven the high efficiency and relative stability of the catalyst.

A novel [(HL)Cu(μ2-Cl)2Cu(HL)]*1.5CH3OH complex was used as an efficient catalyst for the oxidation of alcohols. It was synthesized, using (E)-1-(((2-hydroxypropyl)imino)methyl)naphthalen-2-ol as a monoanionic and tridentate Schiff base ligand, and characterized by IR and UV-Visible spectroscopy and single-crystal X-ray analysis. The geometry of the complex was optimized using the B3LYP level of theory.

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Acknowledgements

We are thankful to University of Jiroft and Vali-e-Asr University of Rafsanjan Research Council for their support on this work. We also thank Dr. Emilio Perez for his valuable comments to improve our project.

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Authors and Affiliations

  1. Faculty of science, Department of Chemistry, University of Jiroft, Jiroft, Iran

    ATENA NAEIMI

  2. Department of Chemistry, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran

    SAMIRA SAEEDNIA

  3. Department of Chemistry, Graduate University of Advanced Technology, Kerman, Iran

    MEHDI YOOSEFIAN

  4. Faculty of Chemistry, University of Isfahan, Isfahan, 81746-73441, Iran

    HADI AMIRI RUDBARI

  5. Università degli Studi di Messina, dip. Scienze Chimiche., Viale Ferdinando S. d’Alcontres, 98166, Messina, Italy

    VIVIANA MOLLICA NARDO

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  1. ATENA NAEIMI
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  2. SAMIRA SAEEDNIA
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  4. HADI AMIRI RUDBARI
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Correspondence to ATENA NAEIMI.

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Supporting Information

Figures S1 and S2 and tables S1 and S2 are available at www.ias.ac.in/chemsci.

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NAEIMI, A., SAEEDNIA, S., YOOSEFIAN, M. et al. A novel dinuclear schiff base copper complex as an efficient and cost effective catalyst for oxidation of alcohol: Synthesis, crystal structure and theoretical studies. J Chem Sci 127, 1321–1328 (2015). https://doi.org/10.1007/s12039-015-0896-9

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  • DOI: https://doi.org/10.1007/s12039-015-0896-9

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