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Synthesis of new heterocyclic ligands and study of the catecholase activity of catalysts based on copper(II)

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Abstract

Four tridentate ligands L1-L4, namely N,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl) pyridin-2-amine: L1, 5-chloro-N,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl) pyridin-2-amine:L2, N,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)thiazol-2-amine:L3 and N,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-6-methylpyridin-2-amine: L4 were synthesized, characterized (by13C NMR, 1H NMR and mass spectroscopy) and employed for the synthesis of copper(II) complexes in situ. These ligands contain three sp2 nitrogen atoms, two pyrazole nitrogen and one pyridine nitrogen, capable of coordinating with copper (II). Then the catalytic properties of certain complexes formed in situ were evaluated to catalyze the oxidation of catechol to o-quinone. Among these complexes, the L1/Cu(CH3COO)2 complex which showed good catalytic activity of the combination 1:1 ligand/metal in THF for this reaction, with a reaction rate of oxidation of catechol to o-quinone equal to 26.37 μmol L−1 min−1.

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Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through Large Groups Project under grant number RGP.2/226/43.

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Authors and Affiliations

  1. Laboratory of Molecular Chemistry, Materials and Envirenment (LMCME), Multidsciplinary Faculty Nador, Nador, Morocco

    Nadia Bouroumane, Mohamed El Boutaybi & Adyl Oussaid

  2. Laboratory of Applied and Environmental Chemistry (LCAE), Mohamed First University, Oujda, Morocco

    Mohamed El Kodadi, Rachid Touzani & Belkheir Hammouti

  3. Laboratoire d’Innovation en Sciences, Technologie et Education (LISTE), CRMEF, Oujda, Morocco

    Mohamed El Kodadi

  4. Catalysis Research Group (CRG), Department of Chemistry, College of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia

    Mohamed Abboud

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  1. Nadia Bouroumane
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Bouroumane, N., El Boutaybi, M., El Kodadi, M. et al. Synthesis of new heterocyclic ligands and study of the catecholase activity of catalysts based on copper(II). Reac Kinet Mech Cat 136, 1545–1562 (2023). https://doi.org/10.1007/s11144-023-02370-7

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