Synthesis 2014; 46(08): 1085-1090
DOI: 10.1055/s-0033-1338598
paper
© Georg Thieme Verlag Stuttgart · New York

Cheap and Easy Synthesis of Highly Functionalized (Het)aryl Iodides via the Aromatic Finkelstein Reaction

Georg Meyer-Eppler
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Fax: +49(228)739608   eMail: arne.luetzen@uni-bonn.de
,
Lea Küchler
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Fax: +49(228)739608   eMail: arne.luetzen@uni-bonn.de
,
Christina Tenten
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Fax: +49(228)739608   eMail: arne.luetzen@uni-bonn.de
,
Christian Benkhäuser
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Fax: +49(228)739608   eMail: arne.luetzen@uni-bonn.de
,
Stefanie Brück
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Fax: +49(228)739608   eMail: arne.luetzen@uni-bonn.de
,
Arne Lützen*
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Fax: +49(228)739608   eMail: arne.luetzen@uni-bonn.de
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Publikationsverlauf

Received: 20. Januar 2014

Accepted after revision: 28. Januar 2014

Publikationsdatum:
26. Februar 2014 (online)


Abstract

Aryl iodides are superior coupling partners in cross-coupling­ reactions compared to the corresponding chlorides or bromides. Unfortunately, the iodides are much more expensive, if commercially available at all, than the other halides. Thus, it is often mandatory to transform the available bromides into the corresponding iodides. The copper-catalyzed aromatic Finkelstein reaction turned out to be the method of choice to prepare a number of highly functionalized iodo(het)aryls, including pyridines, 2,2′-bipyridines, and chiral compounds.

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