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.
Daftar Isi
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
Tentang Penulis
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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