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Imidazo[1,2-a]Pyridine Derivatives–Copper(II) Salts: Highly Effective In Situ Combination for Catecholase

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Abstract

In this work, we were interested in the search for new catalysts for catecholase, whose principle is based on the oxidation reaction of catechol to o-quinone. In this context, a series of ligands derived from 2-phenylimidazo[1,2-a]pyridine-3-carbaldehy were synthesized; then, the complexes formed in situ between these ligands and copper(II) salts, namely Cu(CH3COO)2, CuSO4, Cu(NO3)2 and CuCl2 were examined for their catecholase activity. The kinetics of the reaction was followed by measuring the absorbance versus time with a UV-Vis spectrophotometer for one hour. Compared with other work done in the same framework, the results obtained in this study show that the copper(II)-ligand complexes studied possess excellent catalytic activities for the oxidation of catechol to o-quinone. In particular, the complexes formed between the ligands and the salts Cu(CH3COO)2 and CuSO4 show oxidation rates much higher than those found in the literature. On the other hand, the complexes formed between the ligands and Cu(NO3)2 and CuCl2 also catalyze the reaction, but with much lower oxidation rates than the former. The complex formed between Cu(CH3COO)2 and L1 (2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde) shows the highest catalytic activity with an oxidation rate of 260.41 µmol L−1 s−1, and the complex formed between L6 (6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde) and CuCl2 shows the lowest catalytic activity (43.4 µmol L−1 s−1). This study’s results also show that these complexes’ oxidation efficiency depends on several factors, namely the nature of the substituents on the ligands and the anions of the copper salts.

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Authors and Affiliations

  1. Laboratory of Organic Synthesis, Extraction, and Valorization, Faculty of Sciences Ain Chock, Hassan II University, 20000, Casablanca, Morocco

    Mohamed Moutaouakil, Othmane Roby, Said Tighadouini, Jamal Jamaleddine & Rafik Saddik

  2. Laboratory of Materials Engineering for Environment and Valorization, Faculty of Sciences Ain Chock, University Hassan II, Casablanca, Morocco

    Cherif Abdelmjid

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  1. Mohamed Moutaouakil
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Contributions

RS, CA and ST: conceptualization, supervision, project administration, methodology, resources, data curation, writing of the original draft, review, and editing; MM and OR: conduct of experiment; JJ: project administration. All authors have read and agreed to the published version of the manuscript.

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Correspondence to Rafik Saddik.

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Moutaouakil, M., Abdelmjid, C., Roby, O. et al. Imidazo[1,2-a]Pyridine Derivatives–Copper(II) Salts: Highly Effective In Situ Combination for Catecholase. Chemistry Africa 6, 2621–2630 (2023). https://doi.org/10.1007/s42250-023-00650-2

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