Heterogeneous Enantioselective Hydrogenation

Catalysis by Metal Complexes

Book 31
Springer Science & Business Media
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Heterogeneous Enantioselective Hydrogenation: Theory and Practice reviews the development of enantioselective hydrogenation reaction catalysts. It looks at the first relatively ineffective catalysts right through to modern highly effective enantioselective catalytic systems, comparable in their efficiency to chiral metal complexes and enzymatic systems. The book begins with a summary of the first work on heterogeneous metal catalysts, which showed only the principal possibilities of enantioselective reactions. It then elaborates on metal catalysts which have enantioselectivities close to 100%. Finally, the practical utilization of chiral catalytic systems in processes of hydrogenation is described. The alpha- and beta-hydroxy carboxylic acid esters produced are precursors for manufacturing many synthones used for medicines as well as for monomers used for biodegradable polyesters, both of which have important practical applications.

The volume summarizes more than 800 scientific papers in the field of enantioselective catalytic hydrogenation reactions, mainly those using heterogeneous metal catalysts. It provides detailed explanations of special techniques for the preparation of effective dissymmetric catalysts which provide highly efficient catalytic systems. This book differs from previous publications by virtue of the recommendations for the practical utilization of recently described preparations of metal catalysts.

This book will be an invaluable resource to catalysis researchers as well as to those utilizing the technology.

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About the author

Gerard P. Smith, M.D., is Professor of Psychiatry (Behavioral Neuroscience) at Cornell University Medical College and Director of the Edward W. Bourne Behavioral Research Laboratory at the New York Hospital-Cornell Medical Center.

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Additional Information

Publisher
Springer Science & Business Media
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Published on
May 22, 2007
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Pages
305
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ISBN
9781402042966
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Best For
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Language
English
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Genres
Science / Chemistry / Industrial & Technical
Science / Chemistry / Organic
Science / Chemistry / Physical & Theoretical
Science / Life Sciences / Evolution
Technology & Engineering / Materials Science / General
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Content Protection
This content is DRM protected.
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N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis features all catalytic reactions enabled by N-heterocyclic carbenes (NHCs), either directly as organocatalysts or as ligands for transition metal catalysts. An explosion in the use of NHCs has been reported in the literature during the past seven years making this comprehensive overview highly apropos.

The book begins with an introductory overview of NHCs which could have been subtitled all you need to know about NHCs. The main body of the book is dedicated to applications of NHCs in catalysis. In addition to the success stories of NHCs in metathesis, NHCs in cross coupling and more recently NHCs in organocatalysis, all other less publicized areas are also covered. As the success of NHCs is generally attributed to their potential to stabilize metal centres, the inclusion of a chapter on the decomposition of NHC catalysts is pertinent. The book closes with a chapter describing the applications of NHCs in industrial processes, which is the first coverage of its kind, and brings a unique industrial context to this book.

Included in this book:

Historical aspects of NHCs Synthetic pathways to NHC precursors, free NHCs and complexes Methods of characterisation of NHCs and related complexes Electronic properties of NHCs Steric properties of NHCs and models for their description NHCs for metathesis and cross-coupling reactions NHCs as organocatalysts NHC Transition-Metal mediated oxidations, additions to multiple bonds, polymerisation and oligomerisation, cyclisations, direct arylations, reactions involving CO, C-F and C-H bond activation,... Decomposition of NHC-containing catalysts Industrial applications involving NHC-containing catalysts

N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis provides a fresh view of NHCs since most contributors are young emerging researchers in the field of homogeneous catalysis using NHCs. This group of contributors is complemented by highly established academic researchers and an industrialist. This book is comprehensive, from the basic features of NHCs to the latest advances, hence it is suitable for both the novice and the expert.

N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis features all catalytic reactions enabled by N-heterocyclic carbenes (NHCs), either directly as organocatalysts or as ligands for transition metal catalysts. An explosion in the use of NHCs has been reported in the literature during the past seven years making this comprehensive overview highly apropos.

The book begins with an introductory overview of NHCs which could have been subtitled all you need to know about NHCs. The main body of the book is dedicated to applications of NHCs in catalysis. In addition to the success stories of NHCs in metathesis, NHCs in cross coupling and more recently NHCs in organocatalysis, all other less publicized areas are also covered. As the success of NHCs is generally attributed to their potential to stabilize metal centres, the inclusion of a chapter on the decomposition of NHC catalysts is pertinent. The book closes with a chapter describing the applications of NHCs in industrial processes, which is the first coverage of its kind, and brings a unique industrial context to this book.

Included in this book:

Historical aspects of NHCs Synthetic pathways to NHC precursors, free NHCs and complexes Methods of characterisation of NHCs and related complexes Electronic properties of NHCs Steric properties of NHCs and models for their description NHCs for metathesis and cross-coupling reactions NHCs as organocatalysts NHC Transition-Metal mediated oxidations, additions to multiple bonds, polymerisation and oligomerisation, cyclisations, direct arylations, reactions involving CO, C-F and C-H bond activation,... Decomposition of NHC-containing catalysts Industrial applications involving NHC-containing catalysts

N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis provides a fresh view of NHCs since most contributors are young emerging researchers in the field of homogeneous catalysis using NHCs. This group of contributors is complemented by highly established academic researchers and an industrialist. This book is comprehensive, from the basic features of NHCs to the latest advances, hence it is suitable for both the novice and the expert.

The features of this book which will be of special interest to academic organic chemists are the introduction (Chapter 1), which presents a short course on the concepts and language of heterogeneous catalysis, covers organic reaction mechanisms of hydrogenation (Chapter 2), hydrogenolysis (Chapter 4), and oxidation (Chapter 6), a presents problems and solutions specific for running heterogeneous catalytic organic reactions in solution. These materials can supplement advanced chemistry courses.

Most synthetic organic chemists use a variety of "protecting groups" which they attach to functional groups (reactive groups of atoms) while some reaction is being conducted on another part of the molecule. These protecting groups prevent reactions of the functional groups during other reactions and are removed later by a heterogeneous catalytic method called hydrogenolysis. One unique feature of this book, not found in other books on catalysis, is an exhaustive chapter (Chapter 4) on hydrogenolysis, which is dredged from the recent synthetic literature published by modern organic chemists. Academic organic chemists should find this chapter extremely useful and may wish to adopt the book as a supplement for advanced organic chemistry courses designed for seniors and for graduate students. It will also be useful for professors and their research groups engaged in synthetic organic chemistry.

Many academic organic chemists are not aware of recent advances in heterogeneous enantioselective catalysis (Chapter 3) or in selective low temperature, liquid phase heterogeneous catalytic oxidations by hydrogen peroxide (Chapter 6). These specialty topics are timely and may be new to academic organic chemists and can be used to supplement their advanced courses.

Several features of this book will also be of special interest to industrial chemists who are unfamiliar with heterogeneous catalysis. Many good organic chemists are hire by industry. They synthesize a new compound using standard organic synthetic techniques but are informed by their supervisor that they must convert some of their synthetic steps into heterogeneous catalytic steps. They may not have been exposed to heterogeneous catalysis and have few places to turn. This book offers them a crash course in heterogeneous catalysis as well as many examples of reactions and conditions with which they can start their search.

Those industrial organic chemists already familiar with heterogeneous catalysis will find this book useful as a reference to many examples in the recent literature. They will find recent surface science discoveries correlated with heterogeneous catalysis or organic reactions and mechanistic suggestions designed to stimulate innovative nontraditional thinking about organic reactions on surfaces.

Written by organic chemists for organic chemists Introduces heterogeneous catalysis concepts and language Presents a comprehensive compilation of protecting group removal proceduresCovers liquid-phase hydrogenations, hydrogenolysis, and oxidationsAddresses heterogeneous methods for producing pure enantiomers of chiral productsExamines the emerging field of heterogenized homogeneous catalystsMixes practical applications with mechanistic interpretations
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