C–C Coupling Reaction of Triphenylbismuth(V) Derivatives and Olefins in the Presence of Palladium Nanoparticles Immobilized in Spherical Polyelectrolyte Brushes

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Abstract

Carbon–carbon coupling reactions were carried out by using the triphenylbismuth(V) derivatives Ph3BiX2 (X = O2CH, O2CMe, O2CEt, O2CnPr, O2CnBu, O2CtBu, O2CPh, O2CCH2Cl, O2CCCl3, O2CCF3) and a variety of olefins in the presence of palladium nanoparticles immobilized in spherical polyelectrolyte brushes (Pd@SPB) under mild conditions (50 °C). The effects of the organobismuth derivatives and the unsaturated compounds and the influence of the ratio of solvents (THF and water) on the yield of cross-coupled products were studied. The most active organobismuth compound studied was triphenylbismuth bis(trifluoroacetate), Ph3Bi(O2CCF3)2. This system, which is based on the use oforganobismuth compounds, allows the formation of Heck-type products without the addition of base. Time-dependent product and side-product formation is indicative of a variety of fast (relative to product formation) organobismuth decomposition pathways that lower the overall yield of the coupling reactions. In comparison to homogeneous catalyst systems used for this type of C–C coupling reaction, we only used a very low Pd loading. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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