Sustainable Catalysis

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™, Emselex™, Revatio™, 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™, Viagra™, and Relpax™.

“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)

• Foreword viiPreface ixContributors xiAbbreviations xiii1 Catalytic Reduction of Amides Avoiding LiAlH4 or B2H6 1Deborah L. Dodds and David J. Cole-Hamilton2 Hydrogenation of Esters 37Lionel A. Saudan3 Synthesis of Chiral Amines Using Transaminases 63Nicholas J. Turner and Matthew D. Truppo4 Development of a Sitagliptin Transaminase 75Jacob M. Janey5 Direct Amide Formation Avoiding Poor Atom Economy Reagents 89Benjamin M. Monks and Andrew Whiting6 Industrial Applications of Boric Acid and Boronic Acid-Catalyzed Direct Amidation Reactions 111Joanne E. Anderson, Jannine Cobb, Roman Davis, Peter J. Dunn, Russ N. Fitzgerald, and Alan J. Pettman7 OH Activation for Nucleophilic Substitution 121Jonathan M.J. Williams8 Application of a Redox-Neutral Alcohol Amination in the Kilogram-Scale Synthesis of a GlyT1 Inhibitor 139Martin A. Berliner9 Olefin Metathesis: From Academic Concepts to Commercial Catalysts 163Justyna Czaban, Christian Torborg, and Karol Grela10 Challenge and Opportunity in Scaling-up Metathesis Reaction: Synthesis of Ciluprevir (BILN 2061) 215Nathan Yee, Xudong Wei, and Chris Senanayake11 C–H Activation of Heteroaromatics 233Koji Hirano and Masahiro Miura12 The Discovery of a New Pd/Cu Catalytic System for C–H Arylation and Its Applications in a Pharmaceutical Process 269Jinkun Huang, Xiang Wang, and Johann Chan13 Diarylprolinol Silyl Ethers: Development and Application as Organocatalysts 287Hiroaki Gotoh and Yujiro Hayashi14 Organocatalysis for Asymmetric Synthesis: From Lab to Factory 317Feng Xu15 Catalytic Variants of Phosphine Oxide-Mediated Organic Transformations 339Stephen P. Marsden16 Formation of C–C Bonds Via Catalytic Hydrogenation and Transfer Hydrogenation 363Joseph Moran and Michael J. KrischeIndex 409