Sustainable Catalysis : Challenges and Practices for the Pharmaceutical and Fine Chemical Industries

Opens the door to the sustainable production of pharmaceuticals and fine chemicals Driven by both public demand and government regulations, pharmaceutical and fine chemical manufacturers are increasingly seeking to replace stoichiometric reagents used in synthetic transformations with catalytic routes in order to develop greener, safer, and more cost-effective chemical processes. This book supports the discovery, development, and implementation of new catalytic methodologies on a process scale, opening the door to the sustainable production of pharmaceuticals and fine chemicals. Pairing contributions from leading academic and industrial researchers, Sustainable Catalysis focuses on key areas that are particularly important for the fine chemical and pharmaceutical industries, including chemo-, bio-, and organo-catalytic approaches to C?H, C?N, and C?C bond-forming reactions. Chapters include academic overviews of current innovations and industrial case studies at the process scale, providing new insights into green catalytic methodologies from proof-of-concept to their applications in the synthesis of target organic molecules. Sustainable Catalysis provides the foundation needed to develop sustainable green synthetic procedures, with coverage of such emerging topics as: Catalytic reduction of amides avoiding LiAlH4 or B2H6 Synthesis of chiral amines using transaminases Industrial applications of boric acid and boronic acid catalyzed direct amidation reactions C?H activation of heteroaromatics Organocatalysis for asymmetric synthesis Offering a balanced perspective on current limitations, challenges, and solutions, Sustainable Catalysis is recommended for synthetic organic chemists seeking to develop new methodologies and for industrial chemists dedicated to large-scale process development.Content: Chapter 1 Catalytic Reduction of Amides Avoiding LiAlH4 OR B2H6 (pages 1–36): Deborah L. Dodds and David J. Cole?Hamilton Chapter 2 Hydrogenation of Esters (pages 37–61): Lionel A. Saudan Chapter 3 Synthesis of Chiral Amines Using Transaminases (pages 63–74): Nicholas J. Turner and Matthew D. Truppo Chapter 3 Development of A Sitagliptin Transaminase (pages 75–87): Jacob M. Janey Chapter 5 Direct Amide Formation Avoiding Poor Atom Economy Reagents (pages 89–110): Benjamin M. Monks and Andrew Whiting Chapter 6 Industrial Applications of Boric Acid And Boronic Acid?Catalyzed Direct Amidation Reactions (pages 111–120): Joanne E. Anderson, Jannine Cobb, Roman Davis, Peter J. Dunn, Russ N. Fitzgerald and Alan J. Pettman Chapter 7 OH Activation for Nucleophilic Substitution (pages 121–137): Jonathan M.J. Williams Chapter 8 Application of A Redox?Neutral Alcohol Amination in The Kilogram?Scale Synthesis of A GlyT1 Inhibitor (pages 139–162): Martin A. Berliner Chapter 9 Olefin Metathesis: From Academic Concepts to Commercial Catalysts (pages 163–214): Justyna Czaban, Christian Torborg and Karol Grela Chapter 10 Challenge and Opportunity in Scaling?Up Metathesis Reaction: Synthesis of Ciluprevir (BILN 2061) (pages 215–232): Nathan Yee, Xudong Wei and Chris Senanayake Chapter 11 C?H Activation of Heteroaromatics (pages 233–267): Koji Hirano and Masahiro Miura Chapter 12 The Discovery of A New Pd/Cu Catalytic System For C?H Arylation and Its Applications in A Pharmaceutical Process (pages 269–285): Jinkun Huang, Xiang Wang and Johann Chan Chapter 13 Diarylprolinol Silyl Ethers: Development and Application As Organocatalysts (pages 287–316): Hiroaki Gotoh and Yujiro Hayashi Chapter 14 Organocatalysis for Asymmetric Synthesis: From Lab To Factory (pages 317–337): Feng Xu Chapter 15 Catalytic Variants of Phosphine Oxide?Mediated Organic Transformations (pages 339–361): Stephen P. Marsden Chapter 16 Formation of C?C BONDS via Catalytic Hydrogenation and Transfer Hydrogenation (pages 363–408): Joseph Moran and Michael J. Krische **Opens the door to the sustainable production of pharmaceuticals and fine chemicals** Driven by both public demand and government regulations, pharmaceutical and fine chemical manufacturers are increasingly seeking to replace stoichiometric reagents used in synthetic transformations with catalytic routes in order to develop greener, safer, and more cost-effective chemical processes. This book supports the discovery, development, and implementation of new catalytic methodologies on a process scale, opening the door to the sustainable production of pharmaceuticals and fine chemicals. Pairing contributions from leading academic and industrial researchers, __Sustainable Catalysis__ focuses on key areas that are particularly important for the fine chemical and pharmaceutical industries, including chemo-, bio-, and organo-catalytic approaches to C?H, C?N, and C?C bond-forming reactions. Chapters include academic overviews of current innovations and industrial case studies at the process scale, providing new insights into green catalytic methodologies from proof-of-concept to their applications in the synthesis of target organic molecules. __Sustainable Catalysis__ provides the foundation needed to develop sustainable green synthetic procedures, with coverage of such emerging topics as: * Catalytic reduction of amides avoiding LiAlH4 or B2H6 * Synthesis of chiral amines using transaminases * Industrial applications of boric acid and boronic acid catalyzed direct amidation reactions * C?H activation of heteroaromatics * Organocatalysis for asymmetric synthesis Offering a balanced perspective on current limitations, challenges, and solutions, __Sustainable Catalysis__ is recommended for synthetic organic chemists seeking to develop new methodologies and for industrial chemists dedicated to large-scale process development.Content: Chapter 1 Catalytic Reduction of Amides Avoiding LiAlH4 OR B2H6 (pages 1–36): Deborah L. Dodds and David J. Cole?HamiltonChapter 2 Hydrogenation of Esters (pages 37–61): Lionel A. SaudanChapter 3 Synthesis of Chiral Amines Using Transaminases (pages 63–74): Nicholas J. Turner and Matthew D. TruppoChapter 3 Development of A Sitagliptin Transaminase (pages 75–87): Jacob M. JaneyChapter 5 Direct Amide Formation Avoiding Poor Atom Economy Reagents (pages 89–110): Benjamin M. Monks and Andrew WhitingChapter 6 Industrial Applications of Boric Acid And Boronic Acid?Catalyzed Direct Amidation Reactions (pages 111–120): Joanne E. Anderson, Jannine Cobb, Roman Davis, Peter J. Dunn, Russ N. Fitzgerald and Alan J. PettmanChapter 7 OH Activation for Nucleophilic Substitution (pages 121–137): Jonathan M.J. WilliamsChapter 8 Application of A Redox?Neutral Alcohol Amination in The Kilogram?Scale Synthesis of A GlyT1 Inhibitor (pages 139–162): Martin A. BerlinerChapter 9 Olefin Metathesis: From Academic Concepts to Commercial Catalysts (pages 163–214): Justyna Czaban, Christian Torborg and Karol GrelaChapter 10 Challenge and Opportunity in Scaling?Up Metathesis Reaction: Synthesis of Ciluprevir (BILN 2061) (pages 215–232): Nathan Yee, Xudong Wei and Chris SenanayakeChapter 11 C?H Activation of Heteroaromatics (pages 233–267): Koji Hirano and Masahiro MiuraChapter 12 The Discovery of A New Pd/Cu Catalytic System For C?H Arylation and Its Applications in A Pharmaceutical Process (pages 269–285): Jinkun Huang, Xiang Wang and Johann ChanChapter 13 Diarylprolinol Silyl Ethers: Development and Application As Organocatalysts (pages 287–316): Hiroaki Gotoh and Yujiro HayashiChapter 14 Organocatalysis for Asymmetric Synthesis: From Lab To Factory (pages 317–337): Feng XuChapter 15 Catalytic Variants of Phosphine Oxide?Mediated Organic Transformations (pages 339–361): Stephen P. MarsdenChapter 16 Formation of C?C BONDS via Catalytic Hydrogenation and Transfer Hydrogenation (pages 363–408): Joseph Moran and Michael J. Krische