Solid-Phase Organic Syntheses, Solid-Phase Palladium Chemistry

Overview

This series informs researchers of major accomplishments in solid- phase organic synthesis and provides actual experimental details and specific references. With this series, a reader will be able to sharpen hands-on skills by following the experimental procedures and refining understanding of the science by studying the chosen reactions. More importantly, this series guides readers in designing novel compound libraries, and may also inspire future breakthroughs. This second volume focuses on palladium chemistry ...

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Overview

This series informs researchers of major accomplishments in solid- phase organic synthesis and provides actual experimental details and specific references. With this series, a reader will be able to sharpen hands-on skills by following the experimental procedures and refining understanding of the science by studying the chosen reactions. More importantly, this series guides readers in designing novel compound libraries, and may also inspire future breakthroughs. This second volume focuses on palladium chemistry in solid-phase synthesis, and discusses: palladium catalysts and reactions, procedures for preparation and utilization, ligands, and linker reactions.

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Editorial Reviews

From the Publisher
“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)
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Product Details

Meet 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.

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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

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