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Issue 3, 2013
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Oxidative cycloaddition and cross-coupling processes on unactivated benzene derivatives

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Abstract

Treatment of phenols or anilines containing a sulfonyl group in the presence of a hypervalent iodine reagent promotes a formal dearomatizing [2 + 3] cycloaddition reaction on unactivated benzene and naphthalene derivatives. This process occurs via an intramolecular nucleophilic addition to the Wheland species generated during the oxidative activation. Subsequent treatment under acidic conditions readily transforms the tricyclic system into a biaryl via a formal cross-coupling process.

Graphical abstract: Oxidative cycloaddition and cross-coupling processes on unactivated benzene derivatives

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Article information


Submitted
29 Sep 2012
Accepted
02 Jan 2013
First published
04 Jan 2013

Chem. Sci., 2013,4, 1287-1292
Article type
Edge Article

Oxidative cycloaddition and cross-coupling processes on unactivated benzene derivatives

G. Jacquemot, M. Ménard, C. L'Homme and S. Canesi, Chem. Sci., 2013, 4, 1287
DOI: 10.1039/C2SC22318J

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