Organic Letters · 2006 · 70 citations · 13 references
Natural SciencesChemistryCatalysisOrganic ChemistryReaction EngineeringAddition ReactionsCatalytic MaterialsCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOxidative AdditionConcerted Oxidative AdditionCross CouplingCross-coupling CatalysisOxidative Addition In Cross-coupling CatalysisOxidative CouplingOxidative Cross-couplingPalladium-catalyzed Cross-couplingTransition-metal-catalyzed Cross-coupling
The Suzuki-type cross-coupling reaction of 2,7-dihalofluorenes with 1 equiv of arylboronic acid and Pd2(dba)3/P(t-Bu3) as a catalyst system is investigated. The exclusive formation of the diarylated coupling product demonstrates that "preferential oxidative addition" is also applicable to fluorene monomers due to a controlled intramolecular motion of the regenerated Pd(0) catalyst across the "large" distance between the 2- and the 7-position of one fluorene monomer.
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