Solid–Phase Organic Syntheses, Volume 2: Solid–Phase Palladium Chemistry

Integrates solid–phase organic synthesis with palladiumchemistry

The Wiley Series on Solid–Phase Organic Syntheses keepsresearchers current with major accomplishments in solid–phaseorganic synthesis, providing full experimental details. Followingthe validated, tested, and proven experimental procedures, readerscan easily perform a broad range of complex syntheses needed fortheir own experiments and industrial applications. The series isconveniently organized into themed volumes according to thespecific type of synthesis.

This second volume in the series focuses on palladium chemistryin solid–phase synthesis, exploring palladium catalysts andreactions, procedures for preparation and utilization, ligands, andlinker reactions. The first part of the volume offers acomprehensive overview of the field. Next, the chapters areorganized into three parts:

Each chapter is written by one or more leading internationalexperts in palladium chemistry. Their contributions reflect athorough examination and review of the current literature as wellas their own first–hand laboratory experience. References at theend of each chapter serve as a gateway to the field′sliterature.

The introduction of palladium–mediated, cross–coupling reactionsmore than thirty years ago revolutionized the science ofcarbon–carbon bond formation. It has now become a cornerstone oftoday′s synthetic organic chemistry laboratory. With this volume,researchers in organic and medicinal chemistry have access to asingle resource that explains the fundamentals of palladiumchemistry 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)–PyrazinoneScaffold 25
Vaibhav P. Mehta and Erik V. Van der Eycken

3. One–Step Palladium– and Phenylsilane–Activated Amidation ofSolid–Supported Ally Esters 35
Zheming Ruan, Katy Van Kirk, Christopher B. Cooper, R. MichaelLawrence, and Michael Poss

4. Solid–Phase Reactions of Polymer–Bound Arenesulfonates withAryl Grignard Reagents 41
Kwangyong Park and Chul–Hee Cho

5. Fluorous Synthesis of 3–Aminoimidazo[1,2–a]–Pyridine/PyrazineLibrary 51
Wei Zhang and Yimin Lu

6. Resin–to–Resin Transfer Reactions (RRTR) via SonogashiraCoupling 59
Judit Tulla–Puche, Rita S. Majerle, Fernando Albericio, andGeorge Barany

PART III IMMOBILIZED CATALYSTS AND LIGANDS 67

7. Polymer–supported Palladium Catalysts for Suzuki and HeckReactions 69
Peter Styring

8. Solid–Phase Catalytic Activity of a Polymer–SupportedPalladium Complex 79
Maria M. Dell Anna, Piero Mastrorilli, and Cosimo F.Nobile

9. Polyaniline–immobilized Palladium for Suzuki–Miyaura CouplingReaction in Water 87
Moumita Roy, Pravin R. Likhar, and M. Lakshmi Kantam

10. Synthesis of Polymer–Supported Aryldicyclohexylphosphine foran Efficient Recycling in Suzuki–Miyaura Reactions 91
Katarzyna Glegola and Eric Framery

11. C C or C N Reactions Catalyzed byDiadamanthylphosphine Palladium–Based Catalyst Supported onDab–Dendrimers 97
Karine Heuzé, Agnés Fougeret, Julietta Lemo, and DanielRosario–Amorin

PART IV PALLADIUM–MEDIATED MULTIFUNCTIONAL CLEAVAGE105

12. Solid–Phase Reactions of Resin–Supported Boronic Acids107
François Carreaux, Bertrand Carboni, Herve Deleuze, andChristelle Pourbaix–L Ebraly

13. A Simple Diversity Linker Strategy Using Immobilized EnolPhosphonates as Electrophiles for Suzuki–Miyaura Reactions119
Tom M. Woods

14. Heck Cleavage of Resin–bound Triazenes 129
Sylvia Vanderheiden, Nicole Jung, and Stefan Bräse

15. Pd–Mediated Cleavage from Tetrafluoroarylsulfonate LinkerUnits 139
Andrew N. Cammidge and Zainab Ngaini

16. Palladium–Catalyzed Solid–Phase Synthesis of Allylic Amines145
Richard C. D. Brown and Martin L. Fisher

17. Palladium–Catalyzed Solid–Phase Synthesis of 4–MethylenePyrrolidines 157
Lynda J. Brown, Richard C. D. Brown, and Martin L.Fisher

Index 167

PETER J. H. SCOTT is an Assistant Professor in theDepartment of Radiology at the University of Michigan MedicalSchool. Dr. Scott edited Linker Strategies in Solid–PhaseOrganic Synthesis (also from Wiley) and is the Series Editorfor both the Wiley Series on Radiochemical Syntheses and the WileySeries on Solid–Phase Organic Syntheses.

Overall, though, the adoption of an OrganicSynthesesstyle is an excellent idea and works very well. Along withother related volumes, this collection serves to demystifypolymer–supported methods for palladium–catalysed reactions andprovides a very useful collection of clear methods.  It willcertainly be of interest and use to those new to the field.   (Platinum Metals Review, 1 July 2013)