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Synthesis 2010(16): 2853-2858  
DOI: 10.1055/s-0030-1258145
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© Georg Thieme Verlag Stuttgart ˙ New York

Scaled-Up Transition-Metal-Catalyzed Cross-Coupling Reactions of Thioether-Substituted N-Heterocycles with Organozinc Reagents

Albrecht Metzger, Laurin Melzig, Paul Knochel*
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: Paul.Knochel@cup.uni-muenchen.de;
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Publication History

Received 11 May 2010
Publication Date:
01 July 2010 (online)

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Abstract

A variety of functionalized methylthio-substituted N-heterocycles (pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinazolines, benzothiazoles) undergo smooth palladium- or nickel-catalyzed cross-couplings with highly functionalized organozinc reagents at ambient temperature. No expensive copper(I) salts are required and the coupling reactions proceed readily in the range of up to 20 mmol scale.

Key words

zinc organometallics - cross-coupling - thioether - palladium - nickel

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