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Gooßen, Lukas J. Fachbereich Chemie, Universität Kaiserslautern, Straße, Germany.
Rodríguez, Nuria Fachbereich Chemie, Universität Kaiserslautern, Straße, Germany.
Gooßen, Käthe Fachbereich Chemie, Universität Kaiserslautern, Straße, Germany.
- Carboxylic acids as sources of carbon nucleophiles
- Other decarboxylative couplings
- Related Primary Literature
- Additional Reading
A decarboxylative coupling is a chemical reaction in which a carboxylic acid extrudes a molecule of carbon dioxide (CO2) and in its place forms a bond with an electrophilic carbon atom or heteroatom. The reaction can be employed, for example, in the regioselective synthesis of biaryls from aromatic or heteroaromatic carboxylates and aryl halides or pseudohalides, or for the analogous synthesis of aryl ketones from α-oxocarboxylates [reaction (1)]. In these couplings, the carboxylic acid serves as the source of a carbon nucleophile and reacts with carbon electrophiles. However, by the addition of a stoichiometric oxidant, the reactivity of the system can be turned around so that carboxylic acids may also undergo decarboxylative coupling with nucleophiles. Both the decarboxylation and the coupling steps are mediated by metal catalysts, such as palladium, copper, or silver complexes.
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