Chemistry - A European Journal · 2014 · 73 citations · 73 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalytic MechanismsCross-coupling ReactionsOxidation ReactionsReaction MechanismsReductive EliminationAryl Halide ActivationAryl Halide CouplingLigand Design For Reductive EliminationNucleophile ReactivityPalladium CatalystsPhosphine ReactivityReductive Elimination From Palladium ComplexesReductive Elimination Mechanism
We report an unprecedented BrettPhos ligand supported Pd-catalyzed CO bond-forming reaction of activated aryl halides with primary fluoroalkyl alcohols. We demonstrate that the Phosphine ligand (BrettPhos) possesses the property of altering the mechanistic pathway of reductive elimination from nucleophile to nucleophile. The Pd/BrettPhos catalyst system facilitates the reductive elimination of the oxygen nucleophile through an electronic pathway.
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David W. Old, John P. Wolfe, Stephen L. Buchwald · Journal of the American Chemical Society · 1998 · 811 citations