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Integrates solid-phase organic synthesis with palladium chemistry The Wiley Series on Solid-Phase Organic Syntheses keeps researchers current with major accomplishments in solid-phase organic synthesis, providing full experimental details. Following the validated, tested, and proven experimental procedures, readers can easily perform a broad range of complex syntheses needed for their own experiments and industrial applications. The series is conveniently organized into themed volumes according to the specific type of synthesis. This second volume in the series focuses on palladium chemistry…mehr
Integrates solid-phase organic synthesis with palladium chemistry The Wiley Series on Solid-Phase Organic Syntheses keeps researchers current with major accomplishments in solid-phase organic synthesis, providing full experimental details. Following the validated, tested, and proven experimental procedures, readers can easily perform a broad range of complex syntheses needed for their own experiments and industrial applications. The series is conveniently organized into themed volumes according to the specific type of synthesis. This second volume in the series focuses on palladium chemistry in solid-phase synthesis, exploring palladium catalysts and reactions, procedures for preparation and utilization, ligands, and linker reactions. The first part of the volume offers a comprehensive overview of the field. Next, the chapters are organized into three parts: * Part Two: Palladium-Mediated Solid-Phase Organic Syntheses * Part Three: Immobilized Catalysts and Ligands * Part Four: Palladium-Mediated Multifunctional Cleavage Each chapter is written by one or more leading international experts in palladium chemistry. Their contributions reflect a thorough examination and review of the current literature as well as their own first-hand laboratory experience. References at the end of each chapter serve as a gateway to the field's literature. The introduction of palladium-mediated, cross-coupling reactions more than thirty years ago revolutionized the science of carbon-carbon bond formation. It has now become a cornerstone of today's synthetic organic chemistry laboratory. With this volume, researchers in organic and medicinal chemistry have access to a single resource that explains the fundamentals of palladium chemistry in solid-phase synthesis and sets forth clear, step-by-step instructions for conducting their own syntheses.
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Autorenporträt
PETER J. H. SCOTT is an Assistant Professor in the Department of Radiology at the University of Michigan Medical School. Dr. Scott edited Linker Strategies in Solid-Phase Organic Synthesis (also from Wiley) and is the Series Editor for both the Wiley Series on Radiochemical Syntheses and the Wiley Series on Solid-Phase Organic Syntheses.
Inhaltsangabe
Contributors ix Preface xiii Abbreviations xv PART I INTRODUCTION 1 1. An Introduction to Solid-Phase Palladium Chemistry 3 Carmen Gil PART II PALLADIUM-MEDIATED SPOS 23 2. Pd-Catalyzed Solid-Phase Decoration of the 2(1H)-Pyrazinone Scaffold 25 Vaibhav P. Mehta and Erik V. Van der Eycken 3. One-Step Palladium- and Phenylsilane-Activated Amidation of Solid-Supported Ally Esters 35 Zheming Ruan, Katy Van Kirk, Christopher B. Cooper, R. Michael Lawrence, and Michael Poss 4. Solid-Phase Reactions of Polymer-Bound Arenesulfonates with Aryl Grignard Reagents 41 Kwangyong Park and Chul-Hee Cho 5. Fluorous Synthesis of 3-Aminoimidazo[1,2-a]-Pyridine/Pyrazine Library 51 Wei Zhang and Yimin Lu 6. Resin-to-Resin Transfer Reactions (RRTR) via Sonogashira Coupling 59 Judit Tulla-Puche, Rita S. Majerle, Fernando Albericio, and George Barany PART III IMMOBILIZED CATALYSTS AND LIGANDS 67 7. Polymer-supported Palladium Catalysts for Suzuki and Heck Reactions 69 Peter Styring 8. Solid-Phase Catalytic Activity of a Polymer-Supported Palladium Complex 79 Maria M. Dell'Anna, Piero Mastrorilli, and Cosimo F. Nobile 9. Polyaniline-immobilized Palladium for Suzuki-Miyaura Coupling Reaction in Water 87 Moumita Roy, Pravin R. Likhar, and M. Lakshmi Kantam 10. Synthesis of Polymer-Supported Aryldicyclohexylphosphine for an Efficient Recycling in Suzuki-Miyaura Reactions 91 Katarzyna Glegola and Eric Framery 11. C-C or C-N Reactions Catalyzed by Diadamanthylphosphine Palladium-Based Catalyst Supported on Dab-Dendrimers 97 Karine Heuzé, Agnés Fougeret, Julietta Lemo, and Daniel Rosario-Amorin PART IV PALLADIUM-MEDIATED MULTIFUNCTIONAL CLEAVAGE 105 12. Solid-Phase Reactions of Resin-Supported Boronic Acids 107 François Carreaux, Bertrand Carboni, Herve Deleuze, and Christelle Pourbaix-L'Ebraly 13. A Simple Diversity Linker Strategy Using Immobilized Enol Phosphonates as Electrophiles for Suzuki-Miyaura Reactions 119 Tom M. Woods 14. Heck Cleavage of Resin-bound Triazenes 129 Sylvia Vanderheiden, Nicole Jung, and Stefan Bräse 15. Pd-Mediated Cleavage from Tetrafluoroarylsulfonate Linker Units 139 Andrew N. Cammidge and Zainab Ngaini 16. Palladium-Catalyzed Solid-Phase Synthesis of Allylic Amines 145 Richard C. D. Brown and Martin L. Fisher 17. Palladium-Catalyzed Solid-Phase Synthesis of 4-Methylene Pyrrolidines 157 Lynda J. Brown, Richard C. D. Brown, and Martin L. Fisher Index 167
Contributors ix Preface xiii Abbreviations xv PART I INTRODUCTION 1 1. An Introduction to Solid-Phase Palladium Chemistry 3 Carmen Gil PART II PALLADIUM-MEDIATED SPOS 23 2. Pd-Catalyzed Solid-Phase Decoration of the 2(1H)-Pyrazinone Scaffold 25 Vaibhav P. Mehta and Erik V. Van der Eycken 3. One-Step Palladium- and Phenylsilane-Activated Amidation of Solid-Supported Ally Esters 35 Zheming Ruan, Katy Van Kirk, Christopher B. Cooper, R. Michael Lawrence, and Michael Poss 4. Solid-Phase Reactions of Polymer-Bound Arenesulfonates with Aryl Grignard Reagents 41 Kwangyong Park and Chul-Hee Cho 5. Fluorous Synthesis of 3-Aminoimidazo[1,2-a]-Pyridine/Pyrazine Library 51 Wei Zhang and Yimin Lu 6. Resin-to-Resin Transfer Reactions (RRTR) via Sonogashira Coupling 59 Judit Tulla-Puche, Rita S. Majerle, Fernando Albericio, and George Barany PART III IMMOBILIZED CATALYSTS AND LIGANDS 67 7. Polymer-supported Palladium Catalysts for Suzuki and Heck Reactions 69 Peter Styring 8. Solid-Phase Catalytic Activity of a Polymer-Supported Palladium Complex 79 Maria M. Dell'Anna, Piero Mastrorilli, and Cosimo F. Nobile 9. Polyaniline-immobilized Palladium for Suzuki-Miyaura Coupling Reaction in Water 87 Moumita Roy, Pravin R. Likhar, and M. Lakshmi Kantam 10. Synthesis of Polymer-Supported Aryldicyclohexylphosphine for an Efficient Recycling in Suzuki-Miyaura Reactions 91 Katarzyna Glegola and Eric Framery 11. C-C or C-N Reactions Catalyzed by Diadamanthylphosphine Palladium-Based Catalyst Supported on Dab-Dendrimers 97 Karine Heuzé, Agnés Fougeret, Julietta Lemo, and Daniel Rosario-Amorin PART IV PALLADIUM-MEDIATED MULTIFUNCTIONAL CLEAVAGE 105 12. Solid-Phase Reactions of Resin-Supported Boronic Acids 107 François Carreaux, Bertrand Carboni, Herve Deleuze, and Christelle Pourbaix-L'Ebraly 13. A Simple Diversity Linker Strategy Using Immobilized Enol Phosphonates as Electrophiles for Suzuki-Miyaura Reactions 119 Tom M. Woods 14. Heck Cleavage of Resin-bound Triazenes 129 Sylvia Vanderheiden, Nicole Jung, and Stefan Bräse 15. Pd-Mediated Cleavage from Tetrafluoroarylsulfonate Linker Units 139 Andrew N. Cammidge and Zainab Ngaini 16. Palladium-Catalyzed Solid-Phase Synthesis of Allylic Amines 145 Richard C. D. Brown and Martin L. Fisher 17. Palladium-Catalyzed Solid-Phase Synthesis of 4-Methylene Pyrrolidines 157 Lynda J. Brown, Richard C. D. Brown, and Martin L. Fisher Index 167
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