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Dimethylglyoxime as an efficient ligand for copper-catalyzed hydroxylation of aryl halides

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Abstract

The CuI/dimethylglyoxime (CuI/DMG) catalyzed direct hydroxylation of aryl iodides with CsOH takes place at \(120{\,^{\circ }}\hbox {C}\) in a mixed solvent system (DMSO–\(\hbox {H}_{2}\hbox {O}\),1:1), afforded the corresponding phenols in good to excellent yield. Aryl bromides are found to be less reactive than aryl iodides under these reaction conditions.

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SYNOPSIS. (CuI/DMG) catalyzed synthesis of phenol from aryl iodide and aryl bromide in presence of mixed solvents (\(\hbox {H}_{2}\hbox {O}\): DMSO) is reported in this paper. This protocol is general, economical, easy and convenient for transformation of aryl iodides and bromides to substituted phenols under mild reaction conditions.

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Acknowledgements

The author is thankful to KET’S V. G. Vaze College for financial support. The author is also thankful SAIF, IIT Mumbai for Mass and Instrumentation department Solapur University, Solapur for \(^{1}\hbox {H NMR}\) and \(^{13}\hbox {C NMR}\) analysis.

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Authors and Affiliations

  1. Department of Chemistry, KET’S Vinayak Ganesh Vaze College of Arts, Science and Commerce, Mithagar Road, Mulund (E), Mumbai, Maharashtra, 400 081, India

    Suresh S Shendage

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  1. Suresh S Shendage
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Correspondence to Suresh S Shendage.

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Shendage, S.S. Dimethylglyoxime as an efficient ligand for copper-catalyzed hydroxylation of aryl halides. J Chem Sci 130, 13 (2018). https://doi.org/10.1007/s12039-017-1416-x

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  • DOI: https://doi.org/10.1007/s12039-017-1416-x

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