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Homeopathic Ligand-Free Palladium as a Catalyst in the Heck Reaction. A Comparison with a Palladacycle

Organic Letters · 2003 · Vol. 5(18) · pp. 3285–3288
André H. M. de VriesJan M. C. A. MuldersJohn MommersHuub J. W. HenderickxJohannes G. de Vries

Abstract

[reaction: see text] Ligand-free Pd(OAc)(2) can be used as a catalyst in the Heck reaction of aryl bromides as long as the amount of catalyst is kept between 0.01 and 0.1 mol %. At higher concentrations palladium black forms and the reaction stops. The actual catalyst is monomeric. Palladacycles merely serve as a source of ligand-free palladium in Heck reactions of aryl bromides.

Catalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsChemical synthesis and alkaloidsChemistryPalladiumHeck reactionCatalysisArylLigand (biochemistry)MonomerPolymer chemistryOrganic chemistryCombinatorial chemistry
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References
Palladium-Catalyzed Coupling Reactions of Aryl Chlorides
Angewandte Chemie International Edition · 2002 · 2,674 citations
The Heck Reaction as a Sharpening Stone of Palladium Catalysis
Chemical Reviews · 2000 · 3,857 citations
Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro‐ and Bromoarenes
Angewandte Chemie International Edition in English · 1995 · 816 citations
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