Olefin Metathesis

PREFACE ix

CONTRIBUTORS xi

PART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1

Section I INTRODUCTION 3

1 Olefin Metathesis Reactions: From a Historical Account to Recent 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 Sequences 187
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 REACTIONS 285

8 Applications in the Synthesis of Natural and Biologically Active Molecules 287
Janine Cossy

9 Multifold Ring-Closing Olefin Metatheses in Syntheses of Organometallic Molecules with Unusual Connectivities 311
Tobias Fiedler and John A. Gladysz

10 Industrial Applications of Olefin Metathesis Polymerization 329
Christian Slugovc

11 Commercial Potential of Olefin Metathesis of Renewable Feedstocks 335
Andrew Nickel and Richard L. Pederson

12 Challenges and Opportunities for Scaling the Ring-Closing Metathesis 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 CATALYSTS 369

13 Well-Defined Olefin Metathesis Catalysts Based on Metals of Group 4-7 371
Cezary Pietraszuk

14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397
Georgios C. Vougioukalakis

15 Ruthenium-Indenylidene and Other Alkylidene Containing Olefin Metathesis Catalysts 417
Cesar 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 for Polymerization Reactions 453
Yohann Morin and Regis M. Gauvin

Section V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESIS CATALYSTS 473

18 Novel Concepts in Catalyst Design-a Case Study of Development of Hoveyda-Type Complexes 475
Micha³ Barbasiewicz

19 Theoretical Attempts: "In Silico Olefin Metathesis"-How Can Computers Help in the Understanding of 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 Without Solvent 523
Christian Bruneau and Cedric Fischmeister

23 Olefin Metathesis in Fluorous Phases and in Fluorinated Aromatic Solvents 537
Cezary Samoj³owicz, Anna Kajetanowicz, and Karol Grela

24 Olefin Metathesis in Ionic Liquids 547
Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, Isabelle Dez, Olivier Basle, 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 REVIEW 575
£ukasz Wo´zniak, Grzegorz Zieli´nski, and Karol Grela

Outlook and Perspectives 587

INDEX 589