Solid-Phase Organic Syntheses, Volume 2
Solid-Phase Palladium Chemistry
Wiley Series on Solid-Phase Organic Syntheses Series

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.

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

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.