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Synthesis 2012(2): 184-193  
DOI: 10.1055/s-0031-1289638
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Copper- or Silver-Catalyzed Decarboxylative Deuteration of Aromatic Carboxylic Acids

Martin Rudzki, Ana Alcalde-Aragonés, Wojciech I. Dzik, Nuria Rodríguez, Lukas J. Gooßen*
Department of Chemistry, Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany
Fax: +49(631)2053921; e-Mail: goossen@chemie.uni-kl.de;
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Publikationsverlauf

Received 10 October 2011
Publikationsdatum:
05. Dezember 2011 (online)

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Abstract

The practical utility of decarboxylative transformations in organic synthesis is discussed, and the decarboxylative deuteration of (hetero)aromatic carboxylic acids is disclosed as a further example. Various monodeuterated arenes were synthesized under mild conditions, in a single step from easily accessible aromatic carboxylic acids and deuterium oxide. Copper catalysts were found to have the widest scope, but silver catalysts are superior for some ortho-substituted benzoates. A few substrates, e.g. quinoline-2-carboxylic acid, decarboxylate even in the absence of a metal catalyst.

Key words

arenes - carboxylic acids - catalysis - decarboxylation - deuteration

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