Table 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 Heuze, Agnes Fougeret, Julietta Lemo, and Daniel Rosario-Amorin PART IV PALLADIUM-MEDIATED MULTIFUNCTIONAL CLEAVAGE 105 12. Solid-Phase Reactions of Resin-Supported Boronic Acids 107 Francois 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 Brase 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

About the Author

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.

Reviews

"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)