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Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Developments

Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Developments

Árpád Molnár (Editor)

ISBN: 978-3-527-64830-6 February 2013 692 Pages

 E-Book

$161.99

Description

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
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

“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)