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Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling Using Phosphinous Acids and Dialkyl(chloro)phosphane Ligands
Author(s) -
Wolf Christian,
EkoueKovi Kekeli
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500843
Subject(s) - chemistry , palladium , catalysis , aryl , solvent , monomer , base (topology) , medicinal chemistry , carbonate , organic chemistry , polymer chemistry , alkyl , mathematical analysis , mathematics , polymer
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, ( t Bu 2 POH) 2 PdCl 2 , in 1,4‐dioxane using cesium carbonate as base. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)