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Palladium(0)-Catalyzed Isomerization of (Z)-1,4-Diacetoxy-2-butene − Dependence of η1- or η3-Allylpalladium as a Key Intermediate on the Solvent Polarity
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2001
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Inorganic ChemistryChemical EngineeringCross-coupling ReactionKey Intermediate-1,4-Diacetoxy-2-butene − DependenceBiochemistryEngineeringNatural SciencesCationic η3-AllylpalladiumAlkene MetathesisFormer SolventSolvent PolarityOrganic ChemistryOrganometallic CatalysisCatalysisHomogeneous CatalysisChemistryAsymmetric Catalysis
In the presence of Pd(PPh3)4, (Z)-1,4-diacetoxy-2-butene is selectively isomerized to (E)-1,4-diacetoxy-2-butene in THF while both (E)-1,4-diacetoxy-2-butene and 1,2-diacetoxy-3-butene are obtained in DMF. Evidence to support the involvement of an η1-allylpalladium in the former solvent and of a cationic η3-allylpalladium in the latter as the keys intermediates is presented.