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Synthesis 2010(5): 837-843  
DOI: 10.1055/s-0029-1218598
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Systematic Study of Suzuki-Miyaura Cross-Coupling Reactions on Thiazoleboronic Esters in the 4- and 5-Position

Michael Schnürch*, Johanna Hämmerle, Marko D. Mihovilovic, Peter Stanetty
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria
Fax: +43(1)58801915440; e-Mail: mschnuerch@ioc.tuwien.ac.at;
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Publication History

Received 6 October 2009
Publication Date:
11 December 2009 (online)

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Abstract

A systematic study of the Suzuki-Miyaura cross-coupling reaction of thiazoleboronic esters under microwave conditions is presented. Boronic acid esters were prepared in the 4- and 5-position of the thiazole ring and subsequently cross-coupled with a number of different (hetero)aryl halides. Yields of the coupling process depended on the reactivity of the boronic acid at the particular position in the thiazole system, as hydrolysis and subsequent deboronation was found to be a major side reaction.

Key words

cross-coupling - homogeneous catalysis - heterocycles - palladium - lithiation

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