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A New Highly Active Diphosphane-Palladium(II) Complex as a Catalyst Precursor for the Heck Reaction
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2001
Year
Cis ComplexationCross-coupling ReactionEngineeringCoordination ComplexHeck ReactionCatalyst PrecursorCatalytic SynthesisOrganic ChemistryCyclohexane SkeletonOrganometallic CatalysisCatalysisChair ConformationChemistryMolecular CatalysisInorganic SynthesisBiomolecular Engineering
The new diphosphane ligand cis-1,3-bis[(diphenylphosphanyl)methyl]cyclohexane (4) has been prepared and has allowed the synthesis of the palladium complex cis-[Pd(4)(CO2CF3)2] (6). To obtain cis complexation of the diphosphane in 6 the cyclohexane skeleton adopts a chair conformation with a diaxial orientation of the substituents, a structure that has been verified by an X-ray structure determination. This complex efficiently catalyses the vinylation of iodo- and bromobenzenes in high yields. For the best reaction, with methyl acrylate and iodobenzene, a yield of >98% was obtained with an average turnover frequency of 11 760 h−1 and a turnover number of 1 176 000.