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

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