Olefin Metathesis
Theory and Practice
1. Edition May 2014
608 Pages, Hardcover
Wiley & Sons Ltd
ISBN:
978-1-118-20794-9
John Wiley & Sons
This is a complete examination of the theory and methods of
modern olefin metathesis, one of the most widely used chemical
reactions in research and industry.
* Provides basic information for non-specialists, while also
explaining the latest trends and advancements in the field to
experts
* Discusses the various types of metathesis reactions, including
CM, RCM, enyne metathesis, ROMP, and tandem processes, as well as
their common applications
* Outlines the tools of the trade--from the important
classes of active metal complexes to optimal reaction
conditions--and suggests practical solutions for common
reaction problems
* Includes tables with structures of commercial catalysts, and
recommendations for commercial catalyst suppliers
PREFACE ix
CONTRIBUTORS xi
PART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1
Section I INTRODUCTION 3
1 Olefin Metathesis Reactions: From a Historical Account toRecent Trends 5
Didier Astruc
Section II TYPES OF OLEFIN METATHESIS REACTIONS 37
2 Cross Metathesis 39
Karolina Zukowska and Karol Grela
3 Ring-Closing Metathesis 85
Bianca J. van Lierop, Justin A. M. Lummiss, and Deryn E.Fogg
4 Ene-Yne Metathesis 153
Steven T. Diver and Justin R. Griffiths
5 Domino and Other Olefin Metathesis Reaction Sequences187
Bernd Schmidt and Stefan Krehl
6 Enantioselective Olefin Metathesis 233
Brice Stenne and Shawn K. Collins
7 Olefin Metathesis Polymerization 269
Astrid-Caroline Knall and Christian Slugovc
Section III APPLICATIONS OF OLEFIN METATHESIS REACTIONS285
8 Applications in the Synthesis of Natural and BiologicallyActive Molecules 287
Janine Cossy
9 Multifold Ring-Closing Olefin Metatheses in Syntheses ofOrganometallic Molecules with Unusual Connectivities 311
Tobias Fiedler and John A. Gladysz
10 Industrial Applications of Olefin Metathesis Polymerization329
Christian Slugovc
11 Commercial Potential of Olefin Metathesis of RenewableFeedstocks 335
Andrew Nickel and Richard L. Pederson
12 Challenges and Opportunities for Scaling the Ring-ClosingMetathesis Reaction in the Pharmaceutical Industry 349
Keith R. Fandrick, Jolaine Savoie, Nathan Yee, Jinhua J. Song,and Chris H. Senanayake
PART II DEVELOPMENT OF THE TOOLS 367
Section IV DIFFERENT CLASSES OF OLEFIN METATHESIS CATALYSTS369
13 Well-Defined Olefin Metathesis Catalysts Based on Metals ofGroup 4-7 371
Cezary Pietraszuk
14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397
Georgios C. Vougioukalakis
15 Ruthenium-Indenylidene and Other Alkylidene Containing OlefinMetathesis Catalysts 417
César A. Urbina-Blanco, Stefano Guidone, Steven P. Nolan,and Catherine S. J. Cazin
16 Hoveyda-Type Olefin Metathesis Complexes 437
Yakov Ginzburg and N. Gabriel Lemcoff
17 Schiff Base Catalysts and Other Related Latent Systems forPolymerization Reactions 453
Yohann Morin and Régis M. Gauvin
Section V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESISCATALYSTS 473
18 Novel Concepts in Catalyst Design--a Case Study ofDevelopment of Hoveyda-Type Complexes 475
Micha³ Barbasiewicz
19 Theoretical Attempts: "In Silico OlefinMetathesis"--How Can Computers Help in the Understandingof Metathesis Mechanisms and in Catalysts Development? 483
Albert Poater, Laura Falivene, and Luigi Cavallo
20 Immobilization of Olefin Metathesis Catalysts 495
Michael R. Buchmeiser
21 Olefin Metathesis inWater and Aqueous Media 515
Bruce H. Lipshutz and Subir Ghorai
22 Olefin Metathesis in Green Organic Solvents and WithoutSolvent 523
Christian Bruneau and Cédric Fischmeister
23 Olefin Metathesis in Fluorous Phases and in FluorinatedAromatic Solvents 537
Cezary Samoj³owicz, Anna Kajetanowicz, and KarolGrela
24 Olefin Metathesis in Ionic Liquids 547
Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, IsabelleDez, Olivier Baslé, and Marc Mauduit
25 Purification Strategies in Olefin Metathesis 559
Krzysztof Skowerski and £ukasz Gu³ajski
PART III TABLES AND CHARTS 573
Section VI OLEFIN METATHESIS CATALYSTS--A TABULAR REVIEW575
£ukasz Wo´zniak, Grzegorz Zieli´nski, andKarol Grela
Outlook and Perspectives 587
INDEX 589
CONTRIBUTORS xi
PART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1
Section I INTRODUCTION 3
1 Olefin Metathesis Reactions: From a Historical Account toRecent Trends 5
Didier Astruc
Section II TYPES OF OLEFIN METATHESIS REACTIONS 37
2 Cross Metathesis 39
Karolina Zukowska and Karol Grela
3 Ring-Closing Metathesis 85
Bianca J. van Lierop, Justin A. M. Lummiss, and Deryn E.Fogg
4 Ene-Yne Metathesis 153
Steven T. Diver and Justin R. Griffiths
5 Domino and Other Olefin Metathesis Reaction Sequences187
Bernd Schmidt and Stefan Krehl
6 Enantioselective Olefin Metathesis 233
Brice Stenne and Shawn K. Collins
7 Olefin Metathesis Polymerization 269
Astrid-Caroline Knall and Christian Slugovc
Section III APPLICATIONS OF OLEFIN METATHESIS REACTIONS285
8 Applications in the Synthesis of Natural and BiologicallyActive Molecules 287
Janine Cossy
9 Multifold Ring-Closing Olefin Metatheses in Syntheses ofOrganometallic Molecules with Unusual Connectivities 311
Tobias Fiedler and John A. Gladysz
10 Industrial Applications of Olefin Metathesis Polymerization329
Christian Slugovc
11 Commercial Potential of Olefin Metathesis of RenewableFeedstocks 335
Andrew Nickel and Richard L. Pederson
12 Challenges and Opportunities for Scaling the Ring-ClosingMetathesis Reaction in the Pharmaceutical Industry 349
Keith R. Fandrick, Jolaine Savoie, Nathan Yee, Jinhua J. Song,and Chris H. Senanayake
PART II DEVELOPMENT OF THE TOOLS 367
Section IV DIFFERENT CLASSES OF OLEFIN METATHESIS CATALYSTS369
13 Well-Defined Olefin Metathesis Catalysts Based on Metals ofGroup 4-7 371
Cezary Pietraszuk
14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397
Georgios C. Vougioukalakis
15 Ruthenium-Indenylidene and Other Alkylidene Containing OlefinMetathesis Catalysts 417
César A. Urbina-Blanco, Stefano Guidone, Steven P. Nolan,and Catherine S. J. Cazin
16 Hoveyda-Type Olefin Metathesis Complexes 437
Yakov Ginzburg and N. Gabriel Lemcoff
17 Schiff Base Catalysts and Other Related Latent Systems forPolymerization Reactions 453
Yohann Morin and Régis M. Gauvin
Section V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESISCATALYSTS 473
18 Novel Concepts in Catalyst Design--a Case Study ofDevelopment of Hoveyda-Type Complexes 475
Micha³ Barbasiewicz
19 Theoretical Attempts: "In Silico OlefinMetathesis"--How Can Computers Help in the Understandingof Metathesis Mechanisms and in Catalysts Development? 483
Albert Poater, Laura Falivene, and Luigi Cavallo
20 Immobilization of Olefin Metathesis Catalysts 495
Michael R. Buchmeiser
21 Olefin Metathesis inWater and Aqueous Media 515
Bruce H. Lipshutz and Subir Ghorai
22 Olefin Metathesis in Green Organic Solvents and WithoutSolvent 523
Christian Bruneau and Cédric Fischmeister
23 Olefin Metathesis in Fluorous Phases and in FluorinatedAromatic Solvents 537
Cezary Samoj³owicz, Anna Kajetanowicz, and KarolGrela
24 Olefin Metathesis in Ionic Liquids 547
Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, IsabelleDez, Olivier Baslé, and Marc Mauduit
25 Purification Strategies in Olefin Metathesis 559
Krzysztof Skowerski and £ukasz Gu³ajski
PART III TABLES AND CHARTS 573
Section VI OLEFIN METATHESIS CATALYSTS--A TABULAR REVIEW575
£ukasz Wo´zniak, Grzegorz Zieli´nski, andKarol Grela
Outlook and Perspectives 587
INDEX 589
"In summary, this excellent book, whose artistic eye-catching cover is very elegant, will serve as a perfect companion to chemistry students for gaining a solid basic knowledge of modern metathesis, and also for researchers seeking an in-depth treatment of a specific metathesis topic. It will undoubtedly find its place on our bookshelves and in university and industrial libraries." (Angew. Chem. Int. Ed, 1 February 2015)
KAROL GRELA is a Professor at the Institute of Organic
Chemistry, Polish Academy of Sciences, and the Director of the
Organometallic Synthesis Laboratory at the Biological and Chemical
Research Centre of the Faculty of Chemistry, University of Warsaw,
Poland. Having written over 100 peer-reviewed papers, he is on the
editorial board of Chemistry--a European Journal and on
the advisory board for the European Journal of Organic
Chemistry and Organometallics.
Chemistry, Polish Academy of Sciences, and the Director of the
Organometallic Synthesis Laboratory at the Biological and Chemical
Research Centre of the Faculty of Chemistry, University of Warsaw,
Poland. Having written over 100 peer-reviewed papers, he is on the
editorial board of Chemistry--a European Journal and on
the advisory board for the European Journal of Organic
Chemistry and Organometallics.
