Details

Palladium-Catalyzed Coupling Reactions

Practical Aspects and Future Developments
2. Aufl.

von: Árpád Molnár
147,99 €
Verlag:	Wiley-VCH
Format:	EPUB
Veröffentl.:	14.02.2013
ISBN/EAN:	9783527648306
Sprache:	englisch
Anzahl Seiten:	692

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Beschreibungen

Titelbeschreibung

This handbook and ready reference brings together all significant issues of practical importance in selected topics discussing recent significant achievements for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of key issues of modern-day coupling reactions having emerged and matured in recent years and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications in the pharmaceutical industry, this will equally be of great interest to industrial chemists. From the contents * Palladium-Catalyzed Cross-Coupling Reactions - A General Introduction * High-turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts * The Use of Ordered Porous Solids as Support Materials in Palladium-Catalyzed Cross-Coupling Reactions * Coupling Reactions Induced by Polymer-Supported Catalysts * Coupling Reactions in Ionic Liquids * Cross-Coupling Reactions in Aqueous Media * Microwave-Assisted Synthesis in C-C and C-Heteroatom Coupling Reactions * Catalyst Recycling in Palladium-Catalyzed Carbon-Carbon Coupling Reactions * Nature of the True Catalytic Species in Carbon-Carbon Coupling Reactions with * Heterogeneous Palladium Precatalysts * Coupling Reactions in Continuous Flow Systems * Large-Scale Applications of Palladium-Catalyzed Couplings in the Pharmaceutical Industry

Inhaltsverzeichnis

PREFACE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS - A GENERAL INTRODUCTION Introduction Carbon - Carbon Cross-Coupling Reactions Catalyzed by Palladium The Catalysts Mechanistic Aspects Future Challenges HIGH-TURNOVER HETEROGENEOUS PALLADIUM CATALYSTS IN COUPLING REACTIONS: THE CASE OF PD LOADED ON DEALUMINATED Y ZEOLITES Introduction Various Methodologies to Afford High Turnover Numbers Over Supported Pd Catalysts Structure and Characteristics of Ultrastable Y Zeolites Suzuki - Miyaura Reactions Catalyzed by Pd/USY Catalytic Performance of Pd/USY in Mizoroki - Heck Reactions Conclusion and Perspective PALLADIUM-CATALYZED COUPLING REACTIONS WITH MAGNETICALLY SEPARABLE NANOCATALYSTS Introduction General Considerations Concerning Magnetic Particles as Catalyst Supports Palladium Nanoparticles on Magnetic Supports Molecular Palladium Complexes on Magnetic Supports Outlook THE USE OF ORDERED POROUS SOLIDS AS SUPPORT MATERIALS IN PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS Introduction Catalyst Synthesis and Characterization Carbon - Carbon Couplings Miscellaneous Coupling Reactions The Question of Solution-Phase Catalysis Summary and Future Prospects COUPLING REACTIONS INDUCED BY POLYMER-SUPPORTED CATALYSTS Introduction Polysaccharides Poly(ethylene glycol) Polystyrene Poly(norbornene) Polyacrylamide Polyaniline Poly(N-vinyl-2-pyrrolidone) Polypyrrole Poly(4-vinylpyridine) Ionic Polymers Organometallic Polymers Functionalized Porous Organic Polymers Miscellaneous Polymers Summary and Outlook COUPLING REACTIONS IN IONIC LIQUIDS Introduction Metal Complexes Metal Salts and Metal on Solid Support Metal Nanoparticles Summary and Outlook CROSS-COUPLING REACTIONS IN AQUEOUS MEDIA Introduction Cross-Coupling of Organic Halides to Form C__C Bonds in Aqueous Media Carbon - Heteroatom Coupling Reactions C__H Activation in Aqueous Media Conclusion and Future Prospects MICROWAVE-ASSISTED SYNTHESIS IN C__C AND CARBON - HETEROATOM COUPLING REACTIONS Introduction C__C Bond Formation C__X Bond Formation Conclusions CATALYST RECYCLING IN PALLADIUM-CATALYZED CARBON - CARBON COUPLING REACTIONS Introduction General Issues of Catalyst Recycling Catalyst Systems Providing High, Consistent Yields in Recycling Catalysts Affording the Highest Cumulative TON Values in Recycling Studies Summary Evaluation Future Outlook NATURE OF THE TRUE CATALYTIC SPECIES IN CARBON - CARBON COUPLING REACTIONS WITH HETEROGENEOUS PALLADIUM PRECATALYSTS Introduction Heck Reactions Suzuki Reactions Sonogashira Reactions Concluding Remarks COUPLING REACTIONS IN CONTINUOUS-FLOW SYSTEMS Introduction Coupling Reactions in Flow Palladium Catalysts for Flow Systems Continuous-Flow Technologies for Cross-Coupling Summary and Outlook PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS - INDUSTRIAL APPLICATIONS Introduction Suzuki - Miyaura Reactions Heck - Mizoroki Reactions Sonogashira - Hagihara Reactions Carbonylations Cyanations Negishi Coupling Novel Pd-Catalyzed C__C Cross-Coupling Reaction Buchwald - Hartwig Aminations Pd-Catalyzed C__S Bond Formation Summary and Outlook

Rezension

“This book is an excellent, modern summary of the state of Pd-catalysed coupling reactions. . . This book would be an excellent starting place for an organic chemist who is interested in reducing costs and increasing efficiencies of existing reaction processes or one who is designing new synthetic routes.” (Platinum Metals Review, 1 March 2014) “Overall, the sensible and logical presentation of information and breadth of material covered should make this book a very useful interdisciplinary reference text, while also providing for readers seeking an update on the current state of the art in the field palladium cross-coupling chemistry, especially beyond traditional omogeneous catalysed processes.” (Appl. Organometal. Chem, 1 October 2013)

Autorenportrait

Arpad Molnar is a Professor of Chemistry, Department of Organic Chemistry, University of Szeged (retired in 2008). He earned his C.Sc. and D.Sc. degrees from the Hungarian Academy of Sciences in 1979 and 1990, respectively. He carried out postdoctoral research with Professor Gerard V. Smith at the Southern Illinois University at Carbondale in 1982 - 1983. He worked with Nobel laureate George A. Olah in Loker Hydrocarbon Research Institute at the University of Southern California in Los Angeles in 1992 - 1994 (Moulten Distinguished Fellow), 2001 and 2006 - 2007. He authored about 220 publications including original research papers, reviews, and book chapters. He is the co-author of the books Stereochemistry of Heterogeneous Metal Catalysis (1985), Hydrocarbon Chemistry (1995,2003), Superacid Chemistry (2009), and Hypercarbon Chemistry (2011).

Back cover copy

This handbook and ready reference brings together all signifi cant issues of practical importance in selected topics discussing recent significant achievements for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of key issues of modern-day coupling reactions having emerged and matured in recent years and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications in the pharmaceutical industry, this will equally be of great interest to industrial chemists. From the contents * Palladium-Catalyzed Cross-Coupling Reactions - A General Introduction * High-turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts * The Use of Ordered Porous Solids as Support Materials in Palladium-Catalyzed Cross-Coupling Reactions * Coupling Reactions Induced by Polymer-Supported Catalysts * Coupling Reactions in Ionic Liquids * Cross-Coupling Reactions in Aqueous Media * Microwave-Assisted Synthesis in C-C and C-Heteroatom Coupling Reactions * Catalyst Recycling in Palladium-Catalyzed Carbon-Carbon Coupling Reactions * Nature of the True Catalytic Species in Carbon-Carbon Coupling Reactions with * Heterogeneous Palladium Precatalysts * Coupling Reactions in Continuous Flow Systems * Large-Scale Applications of Palladium-Catalyzed Couplings in the Pharmaceutical Industry