Ligand Design in Metal Chemistry E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 737

Veröffentlichungsjahr: 2016

Beschreibung

The design of ancillary ligands used to modify the structural and reactivity properties of metal complexes has evolved into a rapidly expanding sub-discipline in inorganic and organometallic chemistry. Ancillary ligand design has figured directly in the discovery of new bonding motifs and stoichiometric reactivity, as well as in the development of new catalytic protocols that have had widespread positive impact on chemical synthesis on benchtop and industrial scales.

Ligand Design in Metal Chemistry presents a collection of cutting-edge contributions from leaders in the field of ligand design, encompassing a broad spectrum of ancillary ligand classes and reactivity applications. Topics covered include:

• Key concepts in ligand design
• Redox non-innocent ligands
• Ligands for selective alkene metathesis
• Ligands in cross-coupling
• Ligand design in polymerization
• Ligand design in modern lanthanide chemistry
• Cooperative metal-ligand reactivity
• P,N Ligands for enantioselective hydrogenation
• Spiro-cyclic ligands in asymmetric catalysis

This book will be a valuable reference for academic researchers and industry practitioners working in the field of ligand design, as well as those who work in the many areas in which the impact of ancillary ligand design has proven significant, for example synthetic organic chemistry, catalysis, medicinal chemistry,  polymer science and materials chemistry.

Leseprobe

Ligand Design in Metal Chemistry

Reactivity and Catalysis

Edited by

Mark Stradiotto

Department of Chemistry, Dalhousie University Canada

Rylan J. Lundgren

Department of Chemistry, University of Alberta Canada

This edition first published 2016© 2016 by John Wiley & Sons, Ltd

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Library of Congress Cataloging‐in‐Publication Data

Names: Stradiotto, Mark, author. | Lundgren, Rylan, author.Title: Ligand design in metal chemistry : reactivity and catalysis / [edited by] Mark Stradiotto, Rylan Lundgren.Description: Chichester, UK ; Hoboken, NJ : John Wiley & Sons, 2016. | Includes bibliographical references and index.Identifiers: LCCN 2016023026 | ISBN 9781118839836 (cloth) | ISBN 9781118839812 (epub)Subjects: LCSH: Ligands. | Organometallic compounds–Reactivity. | Homogeneous catalysis.Classification: LCC QD474 .L54 2016 | DDC 546/.3–dc23LC record available at https://lccn.loc.gov/2016023026

A catalogue record for this book is available from the British Library.

List of Contributors

Dinesh C. AluthgeThe University of British Columbia, Canada

Ghenwa BouhadirCNRS, Université Paul Sabatier, France

Didier BourissouCNRS, Université Paul Sabatier, France

Bas de BruinUniversity of Amsterdam, The Netherlands

Ana CaballeroUniversidad de Huelva, Spain

M. Mar Díaz‐RequejoUniversidad de Huelva, Spain

Jennifer Lyn FarmerYork University, Canada

Manuel R. FructosUniversidad de Huelva, Spain

Robert H. GrubbsCalifornia Institute of Technology, USA

Pauline GualcoUniversity of Amsterdam, The Netherlands

Stephen T. LiddleThe University of Manchester, UK

Rylan J. LundgrenUniversity of Alberta, Canada

Parisa MehrkhodavandiThe University of British Columbia, Canada

David P. MillsThe University of Manchester, UK

Robert H. MorrisUniversity of Toronto, Canada

Marc‐André MüllerUniversity of Basel, Switzerland

Michael G. OrganYork University, Canada

Kimberly M. OstenThe University of British Columbia, Canada

Nanda D. PaulIndian Institute of Engineering Science and Technology, India

Philippa R. PayneThe University of British Columbia, Canada

Pedro J. PérezUniversidad de Huelva, Spain

Andreas PfaltzUniversity of Basel, Switzerland

Matthew PompeoYork University, Canada

Demyan E. ProkopchukUniversity of Toronto, Canada

Brendan L. QuigleyCalifornia Institute of Technology, USA

Scott A. RykenThe University of British Columbia, Canada

Laurel L. SchaferThe University of British Columbia, Canada

Samantha A. M. SmithUniversity of Toronto, Canada

Mark StradiottoDalhousie University, Canada

Juan UrbanoUniversidad de Huelva, Spain

Qi‐Lin ZhouNankai University, China

Shou‐Fei ZhuNankai University, China

Foreword

Ligands have the ability to dramatically affect the way that metal complexes react.

In the context of this book, their ability to enhance the reactivity and/or selectivity in the transformation of small molecules is at the heart of the matter. In recent years there has been a growing emphasis on developing an understanding of how structural features of ligands play out in the catalytic transformations in which they are employed. In our work at MIT (described in part by Stradiotto and Lundgren in Chapter 5), we have found that the use of very bulky (steric), electron‐rich (electronic) ligands can be particularly effective in palladium‐catalyzed carbon–heteroatom bond‐forming reactions. We have systematically examined how the change in ligand structure impacts the observed catalytic activity. In addition to the obvious effects of size and the arrangement of substituents, issues such as how coordination number affects the stability and reactivity of the catalytically active intermediates must be taken into account. Most of the basic strategies that we have relied upon were built on the fundamental research conducted by legions of chemists over the years. It is this continued, combined effort, that ultimately leads to successful outcomes.

This book describes the efforts of organic, inorganic and organometallic chemists to apply old principles and develop new ones in an incredible set of contexts. Those with experience in the field realize that good ligands for metals in one area of the periodic table often cannot be used when moving to the right or left. This has led to the need to find different creative solutions to, for example, develop catalysts for hydroamination reactions using group 4 metals rather than for the use of group 8 metals for asymmetric hydrogenation. The many exciting chapters in this book lay out how this has been achieved. Included are some of the most important and topical areas of research in organometallic chemistry. From the perspective of organic synthesis, olefin metathesis, asymmetric hydrogenation and palladium‐catalyzed reactions have become some of the most widely used transformations in both the fine chemical industry and academia. The use of metals other than palladium, rhodium, iridium and ruthenium is of growing interest and chapters describing the use of iron catalysts for asymmetric hydrogenation and coinage metals for a variety of reactions are illustrative of this. The chemistry of early transition metal and lanthanide complexes which possess intriguing reactivity and with very different ligands than, for example, with palladium or rhodium is nicely described in two chapters. Finally, two chapters describe “less conventional” types of ligands: non‐innocent ligands and ambiphilic ligands. The first of these describes a situation where the ligand may change structure or have some sort of secondary function (e.g., recognition). The second reflects ligands that combine donor and acceptor capabilities.

Overall, this book provides a broad overview of both many areas in which ligands hold sway and the means by which they accomplish this. I am certain it will serve as a great resource for students and practitioners in the field alike.

Stephen L. BuchwaldDepartment of ChemistryMassachusetts Institute of TechnologyUSA

Foreword

These are great times for catalysis research. It is widely recognized that catalysis is of key importance in addressing the central societal needs of sustainability, including sustainable chemical synthesis, energy, and the environment. Aided by the current knowledge base in the field, and by advanced computational methods, much progress has already been made in catalytic design aimed at these goals.

The Editors of this book, Professors Mark Stradiotto and Rylan Lundgren, are to be commended for assembling an impressive book of excellent chapters, covering key aspects of the important and timely field of ligand design, which is of course essential to the development of selective and efficient reactions catalyzed by transition metal complexes.

Historically, the development of the fundamentals of ligand design has been largely driven by industrial needs. For example, some of the basic concepts, such as the Tolman ligand cone angle, and the Tolman electronic parameter, described by the Editors in the first chapter of this book, were postulated by Chad Tolman at DuPont Central Research in conjunction with the development of the industrially very important nickel‐catalyzed process of butadiene hydrocyanation to adiponitrile en route to nylon 6,6, pioneered by Bill Drinkard. The success of this ligand design approach has led to further long‐term intensive research on organometallic ligand design, as I had the privilege to personally experience in both industry and academia.

Several useful new families of ligands have evolved in the last few decades. Among those, NHC‐type and pincer‐type ligands have become quite popular and influential in organometallic chemistry and homogeneous catalysis. A particularly fascinating aspect for me is the ability of pincer‐type complexes to effectively function by metal–ligand cooperation, in which both the ligand and the metal are involved in bond breaking and making. This has resulted in recent developments of various environmentally benign synthetic reactions, as well as findings relevant to sustainable energy.

I believe that the reported key concepts of ligand design and the catalytic reactions based on them, covered in this book by leading groups in this field, will capture the imagination of practitioners and students in this exciting field, and will likely lead to further exciting developments in catalysis.

David MilsteinThe Kimmel Centre for Molecular DesignDepartment of Organic ChemistryThe Weizmann Institute of ScienceIsrael

Preface

Synthetic inorganic/organometallic chemistry represents a burgeoning field of study, in which the discovery of fundamentally new bonding motifs and stoichiometric reactivity can in turn underpin the practical development of catalytic substrate transformations on bench‐top and industrial scales. The design and application of ancillary ligands to modify the reactivity properties of metal complexes has figured and continues to figure directly in enabling such advances. A number of important ancillary ligand design strategies have emerged that have served to advance the state‐of‐the‐art across a range of reaction classes.

In recognizing the difficulty associated with comprehensively documenting all aspects of ancillary ligand design within a single, accessible monograph, we opted instead to assemble a diverse collection of cutting‐edge chapters from international leaders in synthetic inorganic/organometallic chemistry and homogeneous catalysis that highlight the breadth and depth of modern ancillary ligand design. In some cases, we have directed the reader to allied texts that may be informative.