Peter J. H. Scott 
Solid-Phase Organic Syntheses, Volume 2 
Solid-Phase Palladium Chemistry

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.

Table of Content

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

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.