Olefin Metathesis

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.

• PREFACE ixCONTRIBUTORS xiPART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1Section I INTRODUCTION 31 Olefin Metathesis Reactions: From a Historical Account to Recent Trends 5Didier AstrucSection II TYPES OF OLEFIN METATHESIS REACTIONS 372 Cross Metathesis 39Karolina ̇ Zukowska and Karol Grela3 Ring-Closing Metathesis 85Bianca J. van Lierop, Justin A. M. Lummiss, and Deryn E. Fogg4 Ene-Yne Metathesis 153Steven T. Diver and Justin R. Griffiths5 Domino and Other Olefin Metathesis Reaction Sequences 187Bernd Schmidt and Stefan Krehl6 Enantioselective Olefin Metathesis 233Brice Stenne and Shawn K. Collins7 Olefin Metathesis Polymerization 269Astrid-Caroline Knall and Christian SlugovcSection III APPLICATIONS OF OLEFIN METATHESIS REACTIONS 2858 Applications in the Synthesis of Natural and Biologically Active Molecules 287Janine Cossy9 Multifold Ring-Closing Olefin Metatheses in Syntheses of Organometallic Molecules with Unusual Connectivities 311Tobias Fiedler and John A. Gladysz10 Industrial Applications of Olefin Metathesis Polymerization 329Christian Slugovc11 Commercial Potential of Olefin Metathesis of Renewable Feedstocks 335Andrew Nickel and Richard L. Pederson12 Challenges and Opportunities for Scaling the Ring-Closing Metathesis Reaction in the Pharmaceutical Industry 349Keith R. Fandrick, Jolaine Savoie, Nathan Yee, Jinhua J. Song, and Chris H. SenanayakePART II DEVELOPMENT OF THE TOOLS 367Section IV DIFFERENT CLASSES OF OLEFIN METATHESIS CATALYSTS 36913 Well-Defined Olefin Metathesis Catalysts Based on Metals of Group 4–7 371Cezary Pietraszuk14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397Georgios C. Vougioukalakis15 Ruthenium-Indenylidene and Other Alkylidene Containing Olefin Metathesis Catalysts 417César A. Urbina-Blanco, Stefano Guidone, Steven P. Nolan, and Catherine S. J. Cazin16 Hoveyda-Type Olefin Metathesis Complexes 437Yakov Ginzburg and N. Gabriel Lemcoff17 Schiff Base Catalysts and Other Related Latent Systems for Polymerization Reactions 453Yohann Morin and Régis M. GauvinSection V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESIS CATALYSTS 47318 Novel Concepts in Catalyst Design—a Case Study of Development of Hoveyda-Type Complexes 475Micha³ Barbasiewicz19 Theoretical Attempts: “In Silico Olefin Metathesis”—How Can Computers Help in the Understanding of Metathesis Mechanisms and in Catalysts Development? 483Albert Poater, Laura Falivene, and Luigi Cavallo20 Immobilization of Olefin Metathesis Catalysts 495Michael R. Buchmeiser21 Olefin Metathesis inWater and Aqueous Media 515Bruce H. Lipshutz and Subir Ghorai22 Olefin Metathesis in Green Organic Solvents and Without Solvent 523Christian Bruneau and Cédric Fischmeister23 Olefin Metathesis in Fluorous Phases and in Fluorinated Aromatic Solvents 537Cezary Samoj³owicz, Anna Kajetanowicz, and Karol Grela24 Olefin Metathesis in Ionic Liquids 547Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, Isabelle Dez, Olivier Baslé, and Marc Mauduit25 Purification Strategies in Olefin Metathesis 559Krzysztof Skowerski and £ukasz Gu³ajskiPART III TABLES AND CHARTS 573Section VI OLEFIN METATHESIS CATALYSTS—A TABULAR REVIEW 575£ukasz Wo´zniak, Grzegorz Zieli´nski, and Karol GrelaOutlook and Perspectives 587INDEX 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)