The Journal of Organic Chemistry · 2005 · 197 citations · 12 references
Natural SciencesChemical EngineeringChemistryCatalysisGreen ChemistryOrganic ChemistryCatalyst DesignCatalyst PreparationCatalytic MaterialsCatalytic MechanismsCross-coupling ReactionsHeterocyclic ChemistryAryl Halide CouplingCatalytic ActivityCatalytic Activity EnhancementCross-coupling CatalysisPalladium-catalyzed Cross-couplingPhenylboronic Acid-based SystemsSuzuki - Miyaura CouplingTransition-metal-catalyzed Cross-coupling
[reaction: see text] A stable and efficient Pd(OAc)2/DABCO (triethylenediamine) catalytic system for Suzuki-Miyaura cross-coupling reaction has been developed. In the presence of Pd(OAc)2 and DABCO, coupling of aryl halides with arylboronic acids was carried out smoothly to afford good to excellent yields and high turnover numbers (TONs) (the maximal TONs were up to 960,000 for the reaction of 1-iodo-4-nitrobenzene with phenylboronic acid) using PEG-400 as the solvent. Moreover, the Pd(OAc)2/DABCO/PEG-400 system could be recycled and reused five times without any loss of catalytic activity for aryl iodides and bromides.
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David W. Old, John P. Wolfe, Stephen L. Buchwald · Journal of the American Chemical Society · 1998 · 811 citations