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Synthesis 2006(18): 2975-2992
DOI: 10.1055/s-2006-950197
DOI: 10.1055/s-2006-950197
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Recent Advances in Pd/C-Catalyzed Coupling Reactions
Further Information
Received
8 May 2006
Publication Date:
15 August 2006 (online)
Publication History
Publication Date:
15 August 2006 (online)
Abstract
A practical approach to multifunctional compounds through palladium on activated carbon (Pd/C)-catalyzed coupling reactions is described. A close correlation of the properties of the Pd/C with reaction efficiency has been observed and depends largely upon the type of reaction. A critical role of the activated carbon is to help palladium disperse sufficiently on the solid support to form the active palladium complex without aggregating to inactive palladium black. The use of Pd/C avoids contamination of the product with palladium and expedites recovery of the metal. The reactions are practical and have been applied to cost-effective large-scale production of multifunctional compounds for drug synthesis.
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1 Introduction
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2 Properties of Pd/C
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3 Coupling Reactions Using Pd/C
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3.1 Heck Coupling
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3.2 Suzuki-Miyaura Coupling
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3.3 Sonogashira Coupling
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3.4 Fukuyama Coupling
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3.5 Cyanation
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3.6 Miscellaneous Reactions
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4 Reaction Mechanism
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5 Conclusion
Key words
catalysis - cross-coupling - heterogeneous catalysis - organometallic reagents - palladium
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