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Issue 8, 2019
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Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: effectively carrying out oxidation reactions in sea water

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Abstract

A simple, efficient, sustainable and economical method for the oxidation of alcohols and amines has been developed based on chloride, a sea abundant anionic catalyst for the practical synthesis of a wide range of carboxylic acids, ketones and imines. Oxidation of aromatic alcohols was carried out using NaCl (20 mol%) as the catalyst, NaOH (50 mol%) and aq. TBHP (4 equiv.) as the oxidant in 55–92% isolated yields. Oxidation of aromatic amines to imines was achieved by using only 20 mol% of NaCl and aq. TBHP (4 equiv.) in 32–93% isolated yields. The chlorine species formed during the reaction as the active oxidation catalyst has been identified as ClO2 for alcohols and ClO/ClO2 for amines by control experiments. This method is mostly free from chromatographic purification, which makes it suitable for large-scale synthesis. We have scaled up to 30 gram scale the synthesis of carboxylic acids and imines in good yields and have also carried out efficiently this new method using filtered sea water as the solvent and catalyst.

Graphical abstract: Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: effectively carrying out oxidation reactions in sea water

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Publication details

The article was received on 08 Feb 2019, accepted on 18 Mar 2019 and first published on 19 Mar 2019


Article type: Communication
DOI: 10.1039/C9GC00497A
Green Chem., 2019,21, 1929-1934

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    Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: effectively carrying out oxidation reactions in sea water

    S. Hazra, A. K. Kushawaha, D. Yadav, P. Dolui, M. Deb and A. J. Elias, Green Chem., 2019, 21, 1929
    DOI: 10.1039/C9GC00497A

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