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Palladium-Catalyzed Coupling Reactions. Practical Aspects and Future Developments

  • ID: 2329798
  • April 2013
  • 692 Pages
  • John Wiley and Sons Ltd
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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 READ MORE >

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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

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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)

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