Handbook of Metathesis
Catalyst Development and Mechanism
2nd Edition
Published on 18. February 2015
448 pages
978-3-527-69400-6 (ISBN)
Description
The second edition of the "go-to" reference in this field is completely updated and features more than 80% new content, with emphasis on new developments in the field, especially in industrial applications. No other book covers the topic in such a comprehensive manner and in such high quality.
Edited by the Nobel laureate R. H. Grubbs and A. G. Wenzel, this volume 1 of the 3-volume work focusses on catalyst development and mechanism. With a list of contributors that reads like a "Who's-Who" of metathesis, this is an indispensable one-stop reference for chemists in academia and industry.
Other available volumes:
Volume 2: Applications in Organic Synthesis, Editors: R. H. Grubbs and D. J. O´Leary
Volume 3: Polymer Synthesis, Editors: R. H. Grubbs and E. Khosravi
Edited by the Nobel laureate R. H. Grubbs and A. G. Wenzel, this volume 1 of the 3-volume work focusses on catalyst development and mechanism. With a list of contributors that reads like a "Who's-Who" of metathesis, this is an indispensable one-stop reference for chemists in academia and industry.
Other available volumes:
Volume 2: Applications in Organic Synthesis, Editors: R. H. Grubbs and D. J. O´Leary
Volume 3: Polymer Synthesis, Editors: R. H. Grubbs and E. Khosravi
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02/2015
2nd Edition
Wiley-VCH
€199.00
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Persons
Robert H. Grubbs received his Ph.D. from Columbia University for work with Ron Breslow. After a postdoctoral year with Jim Collman at Stanford University, he joined the faculty at Michigan State University. In 1978, he moved to the California Institute of Technology, where he is now the Victor and Elizabeth Atkins Professor of Chemistry. Among many other awards, he received the Nobel Prize in 2005 for his research on the metathesis reaction. His research interests include polymer chemistry, organometallic catalysis, and the development of new synthetic organic methodology.
Anna G. Wenzel received her PhD at Harvard University under the guidance of Prof. E. N. Jacobsen. From 2003 to 2006, she joined the group of Prof. R. H. Grubbs as an NIH Postdoctoral Scholar. In 2006, she joined the faculty as an Assistant Professor at the W. M. Keck Science Department in Claremont, California. In 2012, she was promoted to Associate Professor. Her research topics are asymmetric catalysis, organometallic chemistry, and organic synthesis.
Anna G. Wenzel received her PhD at Harvard University under the guidance of Prof. E. N. Jacobsen. From 2003 to 2006, she joined the group of Prof. R. H. Grubbs as an NIH Postdoctoral Scholar. In 2006, she joined the faculty as an Assistant Professor at the W. M. Keck Science Department in Claremont, California. In 2012, she was promoted to Associate Professor. Her research topics are asymmetric catalysis, organometallic chemistry, and organic synthesis.
Content
Preface
HIGH-OXIDATION ON STATE MOLYBDENUM AND TUNGSTEN COMPLEXES RELEVANT TO OLEFIN METATHESIS
Introduction
New Imido Ligands and Synthetic Approaches
Bispyrrolide and Related Complexes
Monoalkoxide Pyrrolide (MAP) Complexes
Reactions of Alkylidenes with Olefins
Olefin and Metallacyclopentane Complexes
Tungsten Oxo Complexes
Bisaryloxides
Other Constructs
Conclusions
ALKANE METATHESIS
Introduction
Alkane Metathesis by Single-Catalyst Systems
Alkane Metathesis by Tandem, Dual-Catalytic Systems
Conclusion
DIASTEREOCONTROL IN OLEFIN METATHESIS: THE DEVELOPMENT OF Z-SELECTIVE RUTHENIUM CATAYLSTS
Introduction
The Challenge of Z-Selective Olefin Metathesis
Previous Strategies
A Serendipitous Discovery
Catalyst Studies
Applications of Z-Selective Ru Metathesis Catalysts
Conclusion
RUTHENIUM OLEFIN METATHESIS CATALYSTS SUPPORTED BY CYCLIC ALKYL AMINOCARBENES (CAACs)
Introduction
Properties and Preparation of CAAC Ligands
CAAC-Supported, Ruthenium Olefin Metathesis Catalysts
Summary
SUPPORTED CATALYSTS AND NONTRADITIONAL REACTION MEDIA
Introduction
Supported Catalyst Systems
Olefin Metathesis in Nontraditional Media
Conclusions
INSIGHTS FROM COMPUTATIONAL STUDIES ON d0 METAL-CATALYZED ALKENE AND ALKYNE METATHESIS AND RELATED REACTIONS
Introduction
Alkene Metathesis
Alkyne Metathesis
Alkane Metathesis
Outlook
COMPUTATIONAL STUDIES OF RUTHENIUM-CATALYZED OLEFIN METATHESIS
Introduction
Computational Investigations of Non-Chelated Ruthenium Catalysts
Computational Investigations of Chelated, Z-Selective Ruthenium Catalysts
Accuray of the Computational Methods
INTERMEDIATES IN OLEFIN METATHESIS
Introduction
Metathesis-Active, Early-Metal Metallacycles
Intermediates in Ruthenium-Catalyzed Olefin Metathesis
Future Directions
FACTORS AFFECTING INITIATION RATES
Introduction
Grubbs Second-Generation Catalyst
Grubbs-Hoveyda-Type Precatalysts
Pyridine Solvates
Piers Catalysts
Indenylidene Carbene Precatalysts
Z-Selective Catalysts
Herrmann-Type, BisNHCs
Conclusions
DEGENERATE METATHESIS
Introduction
Degenerate Metathesis Mechanisms
Degenerate Metathesis with Early Transition-Metal Catalysts
Degenerate Metathesis with Ruthenium Catalysts
Beneficial Effects of Degenerate Metathesis
Conclusions
MECHANISMS OF OLEFIN METATHESIS CATALYST DECOMPOSITION AND METHODS OF CATALYST REACTIVATION
Introduction
Decomposition of Mo and W Imido Alkylidene Catalysts and Related Complexes
Decomposition of Ru Alkylidene Catalysts and Related Complexes
Conclusions
SOLVENT AND ADDITIVE EFFECTS ON OLEFIN METATHESIS
General Introduction
Solvent Effects on Olefin Metathesis
Additive Effects on Olefin Metathesis
Summary
METATHESIS PRODUCT PURIFICATION
Introduction
Chromatographic and Chemical Removal of Ruthenium
Removal by Complexation
Conclusion
RUTHENIUM INDENYLIDENE CATALYSTS FOR ALKENE METATHESIS
Introduction
The Initial Development of Indenylidene Metal Complexes for Alkene Metathesis
Binuclear Indenylidene Ruthenium Catalysts Arising from Ruthenium(arene) Complexes
Preparation of Ruthenium Indenylidene Catalysts from RuCl2(PPh3)3
Ruthenium Catalysts Bearing a Chelating Indenylidene Ligand
Conclusion
HIGH-OXIDATION ON STATE MOLYBDENUM AND TUNGSTEN COMPLEXES RELEVANT TO OLEFIN METATHESIS
Introduction
New Imido Ligands and Synthetic Approaches
Bispyrrolide and Related Complexes
Monoalkoxide Pyrrolide (MAP) Complexes
Reactions of Alkylidenes with Olefins
Olefin and Metallacyclopentane Complexes
Tungsten Oxo Complexes
Bisaryloxides
Other Constructs
Conclusions
ALKANE METATHESIS
Introduction
Alkane Metathesis by Single-Catalyst Systems
Alkane Metathesis by Tandem, Dual-Catalytic Systems
Conclusion
DIASTEREOCONTROL IN OLEFIN METATHESIS: THE DEVELOPMENT OF Z-SELECTIVE RUTHENIUM CATAYLSTS
Introduction
The Challenge of Z-Selective Olefin Metathesis
Previous Strategies
A Serendipitous Discovery
Catalyst Studies
Applications of Z-Selective Ru Metathesis Catalysts
Conclusion
RUTHENIUM OLEFIN METATHESIS CATALYSTS SUPPORTED BY CYCLIC ALKYL AMINOCARBENES (CAACs)
Introduction
Properties and Preparation of CAAC Ligands
CAAC-Supported, Ruthenium Olefin Metathesis Catalysts
Summary
SUPPORTED CATALYSTS AND NONTRADITIONAL REACTION MEDIA
Introduction
Supported Catalyst Systems
Olefin Metathesis in Nontraditional Media
Conclusions
INSIGHTS FROM COMPUTATIONAL STUDIES ON d0 METAL-CATALYZED ALKENE AND ALKYNE METATHESIS AND RELATED REACTIONS
Introduction
Alkene Metathesis
Alkyne Metathesis
Alkane Metathesis
Outlook
COMPUTATIONAL STUDIES OF RUTHENIUM-CATALYZED OLEFIN METATHESIS
Introduction
Computational Investigations of Non-Chelated Ruthenium Catalysts
Computational Investigations of Chelated, Z-Selective Ruthenium Catalysts
Accuray of the Computational Methods
INTERMEDIATES IN OLEFIN METATHESIS
Introduction
Metathesis-Active, Early-Metal Metallacycles
Intermediates in Ruthenium-Catalyzed Olefin Metathesis
Future Directions
FACTORS AFFECTING INITIATION RATES
Introduction
Grubbs Second-Generation Catalyst
Grubbs-Hoveyda-Type Precatalysts
Pyridine Solvates
Piers Catalysts
Indenylidene Carbene Precatalysts
Z-Selective Catalysts
Herrmann-Type, BisNHCs
Conclusions
DEGENERATE METATHESIS
Introduction
Degenerate Metathesis Mechanisms
Degenerate Metathesis with Early Transition-Metal Catalysts
Degenerate Metathesis with Ruthenium Catalysts
Beneficial Effects of Degenerate Metathesis
Conclusions
MECHANISMS OF OLEFIN METATHESIS CATALYST DECOMPOSITION AND METHODS OF CATALYST REACTIVATION
Introduction
Decomposition of Mo and W Imido Alkylidene Catalysts and Related Complexes
Decomposition of Ru Alkylidene Catalysts and Related Complexes
Conclusions
SOLVENT AND ADDITIVE EFFECTS ON OLEFIN METATHESIS
General Introduction
Solvent Effects on Olefin Metathesis
Additive Effects on Olefin Metathesis
Summary
METATHESIS PRODUCT PURIFICATION
Introduction
Chromatographic and Chemical Removal of Ruthenium
Removal by Complexation
Conclusion
RUTHENIUM INDENYLIDENE CATALYSTS FOR ALKENE METATHESIS
Introduction
The Initial Development of Indenylidene Metal Complexes for Alkene Metathesis
Binuclear Indenylidene Ruthenium Catalysts Arising from Ruthenium(arene) Complexes
Preparation of Ruthenium Indenylidene Catalysts from RuCl2(PPh3)3
Ruthenium Catalysts Bearing a Chelating Indenylidene Ligand
Conclusion
