Organic Letters · 2003 · 307 citations · 13 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCarbene ComplexesCatalyst DesignCatalyst SynthesisCoordination ChemistryHeterocyclic ChemistryHeterocyclic CompoundsAmination ReactionsCarbene Complex CrystallographyCarbene Coordination ChemistryCatalysis By Carbene ComplexesCatalytic ActivityPalladium CatalystsSingle-crystal DiffractionSquare Planar Coordination
Palladacycle dimers possessing bridging halides can be easily cleaved by using N-heterocyclic carbenes (NHCs) to generate novel monomeric complexes. The structure of one of these was determined by single-crystal diffraction study and consists of a square-planar coordination around the palladium center where the NHC ligand is trans to the amine of the palladacycle. The complex was found to be equally active in aryl amination and alpha-arylation of ketones even at very low catalyst loading (0.02 mol %). Primary and secondary alkyl/arylamines are equally active partners in coupling reactions. [reaction: see text]
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Highly Active Palladium Catalysts for Suzuki Coupling Reactions
John P. Wolfe, Robert A. Singer, Bryant H. Yang et al. · Journal of the American Chemical Society · 1999 · 1.1K citations
John F. Hartwig, Motoi Kawatsura, Sheila I. Hauck et al. · The Journal of Organic Chemistry · 1999 · 764 citations