Metal-free radical aromatic carbonylations mediated by weak bases

Koziakov, Denis and Jacobi von Wangelin, Axel (2017) Metal-free radical aromatic carbonylations mediated by weak bases. ORGANIC & BIOMOLECULAR CHEMISTRY, 15 (32). pp. 6715-6719. ISSN 1477-0520, 1477-0539

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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.

Item Type: Article
Uncontrolled Keywords: ELECTRON-DONOR INITIATORS; ARYL HALIDES; PHOTOREDOX CATALYSIS; EPSILON-CAPROLACTONE; ARYLDIAZONIUM SALTS; ARENEDIAZONIUM IONS; CARBON-MONOXIDE; ACYL RADICALS; ALKYL IODIDES; ASCORBIC-ACID;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Axel Jacobi von Wangelin
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 13:15
Last Modified: 26 Feb 2019 08:36
URI: https://pred.uni-regensburg.de/id/eprint/1360

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