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A catalytic and mechanistic investigation of a PCP pincer palladium complex in the Stille reaction

By Daniel Olsson, Patrik Nilsson, Mostafa El Masnaouy and Ola Wendt


In an improved procedure, the complex {2,6-bis[(diphenylphosphino)methyl]benzene}chloropalladium(II) (1) was synthesised as its THF adduct and the structure was determined by X-ray crystallography. The catalytic properties of the derivative {2,6-bis[(diphenylphosphino)methyl]benzene} (trifluoroacetato)palladium(II) (2) was investigated in the Stille reaction. Complex 2 proves to be an excellent catalyst for the C-C cross-coupling between trimethyl phenyl stannane and aryl bromides using a very low catalyst loading (0.1-0.0001%), giving high turnover numbers (TONs) up to 6.9 x 10(5). A kinetic investigation of the catalytic reaction suggests a heterogeneous colloidal palladium catalyst formed from the PCP Pd(II) pre-catalyst

Topics: Organic Chemistry
Publisher: 'Royal Society of Chemistry (RSC)'
Year: 2005
DOI identifier: 10.1039/b417908k
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