NDLI: Suzuki Coupling Reactions in Neat Water as the Solvent: Where in the Biphasic Reaction Mixture Do the Catalytic Reaction Steps Occur?

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Suzuki Coupling Reactions in Neat Water as the Solvent: Where in the Biphasic Reaction Mixture Do the Catalytic Reaction Steps Occur?

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Suzuki Coupling Reactions in Neat Water as the Solvent: Where in the Biphasic Reaction Mixture Do the Catalytic Reaction Steps Occur?

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Wirth, Andreas S. Köhler, Klaus Röhlich, Christoph
Description	Author Affiliation: Röhlich C ( Department of Chemistry, Catalysis Research Center, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.)
Abstract	Many reports on water-compatible palladium catalysts have appeared in the recent literature. For hydrophobic substrates, mixtures with pure water are biphasic, and it is widely not regarded that the elusive locality of the catalytic process (in water, the organic layer, or at the phase boundary) has an important impact on the mechanism and efficiency of the reaction. In the present work, for the first time systematic variation of reaction parameters has been performed for Suzuki coupling experiments with chloro- and bromoarenes in pure water. The investigations are not only aimed at the factors influencing the catalytic activity, but also at the effects that may occur particularly in water/organic biphasic media, and on the question as to in which of the two liquid phases the reaction takes place. These investigations have revealed that dilution of the base (in the aqueous layer) and the Pd species (in the organic layer) are detrimental to the reaction, and that phase-transfer processes play a major role in the overall mechanism. A series of experiments with variation of parameters like precatalyst hydrophilicity, organic and water phase volume, additives, stirring rate, base concentration, and so forth, indicate that for the systems under study the reaction occurs in the organic layer. The water phase needs to be present to dissolve and provide polar reactants, and re-absorb side products. The results encourage to pay more regard to the question of phase locality of coupling reactions in water in general.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	48
Volume Number	18
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2012-11-26
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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