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An efficient catalytic system based on 7,8-dihydroxy-4-methylcoumarin and copper(II) for the click synthesis of diverse 1,4-disubstituted-1,2,3-triazoles under green conditions

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Abstract

In this work, the combination of 7,8-dihydroxy-4-methyl coumarin (DHMC) as a novel bidentate O,O-chelating agent and copper(II) acetate monohydrate (2:1 molar ratio) has been found to form an efficient catalytic system. This catalyst provided good to excellent yields in the multi-component click synthesis of 1,4-disubstituted-1,2,3-triazoles by using various structurally diverse organic halides, different non-activated terminal alkynes, and sodium azide. This catalytic system eliminates the need for the isolation of the hazardous azide intermediates which are generated in situ. The reaction is carried out in aqueous phase at room temperature and it can be accelerated by sonication or by increasing the reaction temperature. Moreover, the reaction can be performed in large scale. It is noteworthy that DHMC is commercially available and that it can be easily synthesized with low cost materials.

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Acknowledgments

We gratefully acknowledge the support of this work by the Shiraz University Research Council.

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  1. Department of Chemistry, Shiraz University, Shiraz, 71454, Islamic Republic of Iran

    Hashem Sharghi, Pezhman Shiri & Mahdi Aberi

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  1. Hashem Sharghi
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  2. Pezhman Shiri
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  3. Mahdi Aberi
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Correspondence to Hashem Sharghi.

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Sharghi, H., Shiri, P. & Aberi, M. An efficient catalytic system based on 7,8-dihydroxy-4-methylcoumarin and copper(II) for the click synthesis of diverse 1,4-disubstituted-1,2,3-triazoles under green conditions. Mol Divers 18, 559–575 (2014). https://doi.org/10.1007/s11030-014-9527-5

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