Solid-Phase Organic Syntheses, Volume 2 - Solid-Phase Palladium Chemistry

Informationen zum Autor 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. Klappentext Integrates solid-phase organic synthesis with palladium chemistryThe 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 CleavageEach 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. "Overall, though, the adoption of an Organic Synthesesstyle is an excellent idea and works very well. Along with other related volumes, this collection serves to demystify polymer-supported methods for palladium-catalysed reactions and provides a very useful collection of clear methods. It will certainly be of interest and use to those new to the fi eld." ( Platinum Metals Review , 1 July 2013) Zusammenfassung This series informs researchers of major accomplishments in solid-phase organic synthesis and provides actual experimental details and specific references. With this series, a reader will be able to sharpen hands-on skills by following the experimental procedures and refining understanding of the science by studying the chosen reactions. Inhaltsverzeichnis 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 Jud...

List of contents

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

Report

"Overall, though, the adoption of an Organic Synthesesstyle is an excellent idea and works very well. Along with other related volumes, this collection serves to demystify polymer-supported methods for palladium-catalysed reactions and provides a very useful collection of clear methods. It will certainly be of interest and use to those new to the fi eld." ( Platinum Metals Review , 1 July 2013)

Product details

• Authors: Peter J H Scott, Peter J. H. Scott, PJH Scott, SCOTT PETER J H
• Assisted by: Peter J. H. Scott (Editor), Scott Peter J. H. (Editor)
• Publisher: Wiley, John and Sons Ltd
• Languages: English
• Product format: Hardback
• Released: 04.09.2012
• EAN: 9780470566657
• ISBN: 978-0-470-56665-7
• No. of pages: 184
• Series: Wiley Series on Solid-Phase Organic Syntheses; Wiley Series on Solid-Phase Or; Wiley Series on Solid-Phase Organic Syntheses
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Physical chemistry; Chemie, Organische Chemie, chemistry, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Methods - Synthesis & Techniques, Organische Chemie / Methoden, Synthesen, Verfahren, PHARMAZEUTISCHE CHEMIE