Palladium-Catalyzed Coupling Reactions (eBook)

Árpád Molnár 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).

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