Sustainable Catalysis (eBook)

PETER J. DUNN, PhD, is Global Green Chemistry Lead for Pfizer. Dr. Dunn has played a key role in the development of commercial processes to make several drugs, including Viagra(TM), Emselex(TM), Revatio(TM), and Sampatrilat. K. K. (MIMI) HII, PhD, holds a Readership in Catalysis in the Department of Chemistry at Imperial College London. Her research focuses on the development of sustainable catalytic processes for organic synthesis. MICHAEL J. KRISCHE, PhD, is Director of the Center for Green Chemistry and Catalysis and Robert A. Welch Chair in Science at The University of Texas at Austin. He is the recipient of the Tetrahedron Young Investigator Award, Humboldt Prize, Presidential Green Chemistry Challenge Award, and ACS Elias J. Corey Award. MICHAEL T. WILLIAMS, PhD, is an independent consultant. Previously, he was an executive director at Pfizer and played a key role in the development and commercialization of many drugs, including Zoloft(TM), Viagra(TM), and Relpax(TM).

Foreword vii

Preface ix

Contributors xi

Abbreviations xiii

1 Catalytic Reduction of Amides Avoiding LiAlH4 or B2H6 1

Deborah L. Dodds and David J. Cole-Hamilton

2 Hydrogenation of Esters 37

Lionel A. Saudan

3 Synthesis of Chiral Amines Using Transaminases 63

Nicholas J. Turner and Matthew D. Truppo

4 Development of a Sitagliptin Transaminase 75

Jacob M. Janey

5 Direct Amide Formation Avoiding Poor Atom Economy Reagents
89

Benjamin M. Monks and Andrew Whiting

6 Industrial Applications of Boric Acid and Boronic
Acid-Catalyzed Direct Amidation Reactions 111

Joanne E. Anderson, Jannine Cobb, Roman Davis, Peter J. Dunn,
Russ N. Fitzgerald, and Alan J. Pettman

7 OH Activation for Nucleophilic Substitution 121

Jonathan M.J. Williams

8 Application of a Redox-Neutral Alcohol Amination in the
Kilogram-Scale Synthesis of a GlyT1 Inhibitor 139

Martin A. Berliner

9 Olefin Metathesis: From Academic Concepts to Commercial
Catalysts 163

Justyna Czaban, Christian Torborg, and Karol Grela

10 Challenge and Opportunity in Scaling-up Metathesis Reaction:
Synthesis of Ciluprevir (BILN 2061) 215

Nathan Yee, Xudong Wei, and Chris Senanayake

11 C-H Activation of Heteroaromatics 233

Koji Hirano and Masahiro Miura

12 The Discovery of a New Pd/Cu Catalytic System for C-H
Arylation and Its Applications in a Pharmaceutical Process
269

Jinkun Huang, Xiang Wang, and Johann Chan

13 Diarylprolinol Silyl Ethers: Development and Application as
Organocatalysts 287

Hiroaki Gotoh and Yujiro Hayashi

14 Organocatalysis for Asymmetric Synthesis: From Lab to Factory
317

Feng Xu

15 Catalytic Variants of Phosphine Oxide-Mediated Organic
Transformations 339

Stephen P. Marsden

16 Formation of C-C Bonds Via Catalytic Hydrogenation and
Transfer Hydrogenation 363

Joseph Moran and Michael J. Krische

Index 409

"In brief, I have read this book with pleasure and I
recommend it to all chemists working or getting started in the
field of catalysis." (Angew. Chem. Int.
Ed., 1 October 2014)