Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Using Phosphinous Acids and Dialkyl(chloro)phosphane Ligands

The use of eleven palladium complexes having monomeric and μ‐chloro‐bridged dimeric structures and either bulky dialkyl‐ and diarylphosphinous acid ligands (POPd, POPd‐Br, POPd1, POPd2, POPd6, POPd7, Ph1‐Phoxide) or dialkyl(chloro)phosphane ligands (PXPd, PXPd2, PXPd6, PXPd7) for Suzuki–Miyaura coup...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2006-04, Vol.2006 (8), p.1917-1925
Main Authors: Wolf, Christian, Ekoue-Kovi, Kekeli
Format: Article
Language:English
Subjects:
Biaryls
Cross-coupling
Homogeneous catalysis
Palladium
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Summary:The use of eleven palladium complexes having monomeric and μ‐chloro‐bridged dimeric structures and either bulky dialkyl‐ and diarylphosphinous acid ligands (POPd, POPd‐Br, POPd1, POPd2, POPd6, POPd7, Ph1‐Phoxide) or dialkyl(chloro)phosphane ligands (PXPd, PXPd2, PXPd6, PXPd7) for Suzuki–Miyaura coupling reactions has been evaluated. Screening and optimization of catalyst loading, solvent, temperature, and base showed that excellent results can be obtained with electron‐deficient and electron‐rich aryl iodides, bromides, and chlorides in the presence of 2.5 mol‐% of palladium–phosphinous acid POPd, (tBu2POH)2PdCl2, in 1,4‐dioxane using cesium carbonate as base. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500843