Part Three: Immobilized
Trade Review
“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)
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 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
