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Experimental evidence for the formation of cationic intermediates during iodine(III)-mediated oxidative dearomatization of phenols

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Abstract

Iodine(III)-based oxidants are commonly used reagents for the oxidative dearomatization of phenols. Having a better understanding of the mechanism through which these reactions proceed is important for designing new iodine(III)-based reagents, catalysts, and reactions. We have performed a Hammett analysis of the oxidative dearomatization of substituted 4-phenylphenols. This study confirms that iodine(III)-mediated oxidative dearomatizations likely proceed through cationic phenoxenium ions and not the direct addition of a nucleophile to an iodine-bound phenol intermediate.

Graphical abstract: Experimental evidence for the formation of cationic intermediates during iodine(iii)-mediated oxidative dearomatization of phenols

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Publication details

The article was received on 12 Jul 2018, accepted on 31 Aug 2018 and first published on 01 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB01652F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Experimental evidence for the formation of cationic intermediates during iodine(III)-mediated oxidative dearomatization of phenols

    T. Tang and A. M. Harned, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01652F

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