Sustainable Catalysis

Opens the door to the sustainable production ofpharmaceuticals and fine chemicalsDriven by both public demand and government regulations,pharmaceutical and fine chemical manufacturers are increasinglyseeking to replace stoichiometric reagents used in synthetictransformations with catalytic routes in order to develop greener,safer, and more cost-effective chemical processes. This booksupports the discovery, development, and implementation of newcatalytic methodologies on a process scale, opening the door to thesustainable production of pharmaceuticals and fine chemicals.Pairing contributions from leading academic and industrialresearchers, Sustainable Catalysis focuses on key areas thatare particularly important for the fine chemical and pharmaceuticalindustries, including chemo-, bio-, and organo-catalytic approachesto C-H, C-N, and C-C bond-forming reactions.Chapters include academic overviews of current innovations andindustrial case studies at the process scale, providing newinsights into green catalytic methodologies from proof-of-conceptto their applications in the synthesis of target organicmolecules.Sustainable Catalysis provides the foundation needed todevelop sustainable green synthetic procedures, with coverage ofsuch emerging topics as:* Catalytic reduction of amides avoiding LiAlH4 or B2H6* Synthesis of chiral amines using transaminases* Industrial applications of boric acid and boronic acidcatalyzed direct amidation reactions* C-H activation of heteroaromatics* Organocatalysis for asymmetric synthesisOffering a balanced perspective on current limitations,challenges, and solutions, Sustainable Catalysis isrecommended for synthetic organic chemists seeking to develop newmethodologies and for industrial chemists dedicated to large-scaleprocess development.

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 Reagents89Benjamin M. Monks and Andrew Whiting6 Industrial Applications of Boric Acid and BoronicAcid-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 theKilogram-Scale Synthesis of a GlyT1 Inhibitor 139Martin A. Berliner9 Olefin Metathesis: From Academic Concepts to CommercialCatalysts 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-HArylation and Its Applications in a Pharmaceutical Process269Jinkun Huang, Xiang Wang, and Johann Chan13 Diarylprolinol Silyl Ethers: Development and Application asOrganocatalysts 287Hiroaki Gotoh and Yujiro Hayashi14 Organocatalysis for Asymmetric Synthesis: From Lab to Factory317Feng Xu15 Catalytic Variants of Phosphine Oxide-Mediated OrganicTransformations 339Stephen P. Marsden16 Formation of C-C Bonds Via Catalytic Hydrogenation andTransfer Hydrogenation 363Joseph Moran and Michael J. KrischeIndex 409