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Issue 32, 2017
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Metal-free radical aromatic carbonylations mediated by weak bases

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Abstract

We report a new method of metal-free alkoxycarbonylation. This reaction involves the generation of aryl radicals from arenediazonium salts by a very weak base (HCO2Na) under mild conditions. Subsequent radical trapping with carbon monoxide and alcohols gives alkyl benzoates. The conditions (metal-free, 1 equiv. base, MeCN, r.t., 3 h) tolerate various functional groups (I, Br, Cl, CF3, SF5, NO2, ester). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism.

Graphical abstract: Metal-free radical aromatic carbonylations mediated by weak bases

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Publication details

The article was received on 28 Jun 2017, accepted on 27 Jul 2017 and first published on 27 Jul 2017


Article type: Communication
DOI: 10.1039/C7OB01572K
Citation: Org. Biomol. Chem., 2017,15, 6715-6719
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    Metal-free radical aromatic carbonylations mediated by weak bases

    D. Koziakov and A. Jacobi von Wangelin, Org. Biomol. Chem., 2017, 15, 6715
    DOI: 10.1039/C7OB01572K

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