Issue 32, 2017

Metal-free radical aromatic carbonylations mediated by weak bases

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

Supplementary files

Article information

Article type
Communication
Submitted
28 Jun 2017
Accepted
27 Jul 2017
First published
27 Jul 2017

Org. Biomol. Chem., 2017,15, 6715-6719

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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