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Title Organometallic chemistry in industry : a practical approach / edited by Thomas J. Colacot, Carin C.C. Johansson Seechurn ; with a foreword by Robert H. Grubbs
Published Weinheim : Wiley-VCH, [2020]
©2020

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Description 1 online resource (338 pages) : illustrations
Contents Cover -- Title Page -- Copyright -- Contents -- Foreword -- Preface -- Chapter 1 Industrial Milestones in Organometallic Chemistry -- 1.1 Definition of Organometallic and Metal-Organic Compounds -- 1.1.1 Applications and Key Reactivity -- 1.1.1.1 Electronic Applications -- 1.1.1.2 Polymers -- 1.1.1.3 Organic Synthesis -- 1.2 Industrial Process Considerations -- 1.3 Brief Notes on the Historical Development of Organometallic Chemistry for Organic Synthesis Applications Pertaining to the Contents of this Book -- 1.3.1 Synthesis of Stoichiometric Organometallic Reagents
1.3.1.1 Conventional Batch Synthesis -- 1.3.1.2 Organometallics in Flow -- 1.3.2 Cross-coupling Reactions -- 1.3.2.1 C-HBond Activation -- 1.3.2.2 Carbonylation -- 1.3.2.3 Catalysis in Water -- Micellar Catalysis -- 1.3.3 Hydrogenation Reactions -- 1.3.4 Olefin Formation Reactions -- 1.3.4.1 Wittig Reaction -- 1.3.4.2 Metathesis Reactions -- 1.3.4.3 Dehydrative Decarbonylation -- 1.3.4.4 Olefins as Starting Materials -- 1.3.5 Poly- or Oligomerization Processes -- 1.3.6 Photoredox Catalysis for Organic Synthesis -- 1.4 Conclusion and Outlook -- Biography -- References
Chapter 2 Design, Development, and Execution of a Continuous-flow-Enabled API Manufacturing Route -- 2.1 Continuous-flow-Enabled Synthetic Strategy -- 2.2 Design and Scale-up of Chan-Lam Coupling -- 2.2.1 Development of Homogeneous Conditions -- 2.2.2 Application of a Platform Technology to Aerobic Oxidation -- 2.2.3 Optimization of Reaction and Workup Parameters -- 2.2.4 Safety Considerations for Aerobic Oxidation on Scale -- 2.2.5 Continuous Scale-up and Manufacturing -- 2.3 Design and Scale-up of a Buchwald-Hartwig Cross-coupling -- 2.3.1 Initial Screening
2.3.2 Synthesis and Isolation of Pd(dba)DPEPhos Precatalyst -- 2.3.3 Workup Procedure, Metal Removal, and Crystallization -- 2.3.4 Scale-up and Manufacturing -- 2.4 Impurity Control -- 2.4.1 Solubility and Impurity Spiking Studies -- 2.5 Conclusions -- Biography -- References -- Chapter 3 Continuous Manufacturing as an Enabling Technology for Low-Temperature Organometallic Chemistry -- 3.1 Introduction -- 3.2 Organo-Li and Mg Processes in Flow Mode -- 3.2.1 Technological Advantages of Flow Technology Compared to Traditional Batch Operation -- 3.2.2 Temperature Profile of Continuous Flow Reactions
3.2.3 Flash Chemistry: Functional Group Tolerance -- 3.2.4 Flash Chemistry: Selectivity -- 3.2.5 Flash Chemistry: Stoichiometry and Chemoselectivity -- 3.3 Continuous Flow Technology -- 3.3.1 Clogging as a Major Hurdle in Flow Chemistry -- 3.3.2 Start-up and Shutdown Operation -- 3.3.3 Material of Construction -- 3.3.4 Safety Concept and Emergency Strategies -- 3.4 Development of a Flow Process -- 3.4.1 Screening Phase: Feasibility Study -- 3.4.2 Process Development Phase: Extended Evaluations Including Technical Feasibility -- 3.5 Literature Examples: Flow Processes on Multi 100 g Scale
Summary "Showcases the important role of organometallic chemistry in industrial applications and includes practical examples and case studies This comprehensive book takes a practical approach to how organometallic chemistry is being used in industrial applications. It uniquely offers numerous, real-world examples and case studies that aid working R & D researchers as well as Ph. D. and postdoc students preparing to ace interviews in order to enter the workforce. Edited by two world-leading and established industrial chemists, the book covers flow chemistry (catalytic and non-catalytic organometallic chemistry), various cross-coupling reactions (C-C, C-N, and C-B) in classical batch chemistry, conjugate addition reactions, metathesis, and C-H arylation and achiral hydrogenation reactions. Beginning with an overview of the many industrial milestones within the field over the years, Organometallic Chemistry in Industry: A Practical Approach provides chapters covering: the design, development, and execution of a continuous flow enabled API manufacturing route; continuous manufacturing as an enabling technology for low temperature organometallic chemistry; the development of a nickel-catalyzed enantioselective Mizoroki-Heck coupling; and the development of iron-catalyzed Kumada cross-coupling for the large scale production of Aliskiren intermediates."-- Provided by publisher
Notes 3.5.1 Manufacture of Verubecestat (MK-8931)
Bibliography Includes bibliographical references and index
Notes Print version record
Subject Organometallic chemistry.
SCIENCE -- Chemistry -- Organic.
Organometallic chemistry
Form Electronic book
Author Colacot, Thomas, editor.
Seechurn, Carin C. C. Johansson, editor
Grubbs, Robert H., writer of foreword.
ISBN 9783527819201
3527819207
9783527819195
3527819193
9783527819171
3527819177