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Synthesis 2010(1): 85-90  
DOI: 10.1055/s-0029-1217082
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,2′-Bipyridines via Suzuki-Miyaura Cross-Coupling

Christoph Gütz, Arne Lützen*
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)739608; e-Mail: arne.luetzen@uni-bonn.de;
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Publication History

Received 26 August 2009
Publication Date:
26 October 2009 (online)

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Abstract

For a long time, the Suzuki-Miyaura cross-coupling reaction could not be used for the synthesis of 2,2′-bipyridines due to the lack of sufficiently stable 2-pyridylboron compounds. Stabilized 2-pyridylboronic acid esters recently developed by Hodgson, however, were found to be ideally suited for this purpose. Two general protocols could be developed and demonstrated to be valuable alternatives, which can be used very efficiently for the synthesis of functionalized 2,2′-bipyridines.

Key words

cross-coupling reactions - bipyridines - palladium - 2-pyridylboronic acid esters - Suzuki-Miyaura reaction

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