ChemCatChem · 2012 · 17 citations · 82 references
Natural SciencesChemical EngineeringChemistryCatalysisMaterials ChemistryOrganic ChemistryCatalyst DesignCatalyst PreparationCatalyst SynthesisCatalytic MaterialsNanocatalysisSupported CatalystsCatalytic FunctionalizationHeterogeneous Catalyst DesignHeterogeneous Catalyst PreparationKetonesNanostructured CatalystsNegishi CouplingOrganozinc CouplingPalladium Catalysts
Abstract The Negishi coupling of aryl bromides or acyl chlorides with organozinc chlorides catalyzed by a palladium bipyridyl complex anchored on nanosized mobile crystalline material 41 (MCM‐41) were investigated. The reactions proceeded smoothly with a very low catalyst loading in THF at 70 °C for electron‐deficient aryl bromides, which gave good to high yields of the Negishi coupling products. However, reactions in toluene at 110 °C were required if electron‐rich aryl bromides were employed. For acyl chlorides, the reactions could be performed in THF at 50 °C and the corresponding ketones and ynones were obtained in high yields. After centrifugation, it was possible to easily recover the supported catalyst from the reaction mixture, and this could be reused several times without any retreatment or regeneration with only a slight decrease in activity.
82
Ei‐ichi Negishi, Zhihong Huang, Guangwei Wang et al. · Accounts of Chemical Research · 2008 · 529 citations