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Synlett 2003(12): 1874-1876  
DOI: 10.1055/s-2003-41472
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction

Eddy Maertena, Fatima Hassounaa, Samuel Couve-Bonnairea, André Mortreuxa, Jean-François Carpentierb, Yves Castanet*a
a Laboratoire de Catalyse de Lille, UMR 8010 CNRS, Université de Lille 1, ENSCL, BP 108, 59652, Villeneuve d’Ascq Cedex, France
Fax: +33(3)20436585; e-Mail: yves.castanet@ensc-lille.fr;
b Organométalliques et Catalyse, UMR 6509 CNRS, Université de Rennes 1, Institut de Chimie, Campus de Beaulieu, 35042, Rennes Cedex, France
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Publication History

Received 17 June 2003
Publication Date:
19 September 2003 (online)

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Abstract

The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.

Key words

palladium - N-heterocyclic carbene ligand - pyridyl chloride

    References

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9

In a number of coupling reactions of aryl chlorides, it was found that a 1:1 Pd-ligand ratio (ligand = N-heterocyclic carbene, phosphine, …) led to optimum reaction rates (see ref. 2 and ref. 5b for N-heterocyclic carbene ligands).

10

TOF: turnover frequencies defined as the number of moles of substrate transformed per mole of catalyst and per hour calculated after one hour of reaction.