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o-Iodoxybenzoic acid mediated generation of aryl free radicals: synthesis of stilbenes through C–C cross-coupling with β-nitrostyrenes

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Abstract

The generation of an aryl free radicals in the presence of nitrostyrenes through a combination of aryl hydrazines and o-iodoxybenzoic acid led to the synthesis of stilbenes by forming a new carbon–carbon bond after subsequent elimination of a nitrosyl radical. The symmetrical and unsymmetrical stilbenes with excellent E-selectivity were synthesized in good yields, with advantages of broad substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,3-dimethoxy-5-(4-methoxystyryl)benzene.

Graphical abstract: o-Iodoxybenzoic acid mediated generation of aryl free radicals: synthesis of stilbenes through C–C cross-coupling with β-nitrostyrenes

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Publication details

The article was received on 30 Nov 2017, accepted on 14 Jan 2018 and first published on 15 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ04701K
Citation: New J. Chem., 2018, Advance Article
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    o-Iodoxybenzoic acid mediated generation of aryl free radicals: synthesis of stilbenes through C–C cross-coupling with β-nitrostyrenes

    G. Wagh, S. Autade, P. C. Patil and K. G. Akamanchi, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ04701K

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