Enabling tools and techniques for organic synthesis : a practical guide to experimentation, automation, and computation /: a practical guide to experimentation, automation, and computation. (2023)

• Record Type: Book
• Further Information: Note: Edited by Stephen G. Newman.
• Editors: Newman, Stephen G, 1985-
• Contents: List of Contributors xv Preface xix 1 Biocatalysis 101 – A Chemist’s Guide to Starting Biocatalysis 1; Pablo Díaz- Kruik, David Lim, and Francesca Paradisi Glossary 1 1.1 Introduction 1 1.1.1 Enzymes – the Green and Sustainable Way of the Future 1 1.1.2 Enzymatic and Organic Catalysis Are Not too Different from Each Other 3 1.1.3 Enzymes 101 4 1.2 When Should I Choose an Enzyme over a Chemical Catalyst? 4 1.3 Key Considerations for Running Biocatalytic Reactions 6 1.3.1 Dispelling Myths 6 1.3.1.1 Enzymes Are Not Safe to Use 7 1.3.1.2 Enzymes Are Not as Readily Available as Chemical Catalysts 7 1.3.1.3 Enzymes Are Seldom Useful Due to Their Limited Substrate Scope 7 1.3.1.4 The Cost of Enzyme Production Is Very High 8 1.3.1.5 Enzymes Are Functionally Unstable Under Organic Conditions 9 1.3.1.6 Sustainability 9 1.3.2 Challenges of Using Enzymes: the Need for Strict Reaction Conditions 9 1.3.2.1 Enzymes from Extremophiles 10 1.3.2.2 Solvents (and Co- solvents) 10 1.3.2.3 Concentration and Ionic Strength of the Buffer 10 1.3.2.4 pH Dependence 11 1.3.2.5 Concentration of Reactants 11 1.3.2.6 Enzyme Concentration 12 1.3.2.7 Enzyme Forms 12 1.3.2.8 Toxicity 13 1.3.3 What Do I Need to Start Biocatalytic Experiments in My Lab? 13 1.3.4 Additional Considerations 14 1.4 Transformations Catalyzed by Enzymes 15 1.4.1 EC – The Enzyme Commission Number 15 1.4.1.1 EC 1 – Oxoreductases 15 1.4.1.2 EC 2 – Transferases 16 1.4.1.3 EC 3 – Hydrolases 16 1.4.1.4 EC 4 – Lyases 17 1.4.1.5 EC 5 – Isomerases 18 1.4.1.6 EC 6 – Ligases 18 1.4.1.7 EC 7 – Translocases 18 1.4.2 Some Applications of Selected Commercially Available Enzymes 19 1.4.2.1 Horseradish Peroxidase 19 1.4.2.2 Lysozyme 19 1.4.2.3 Trypsin 20 1.4.2.4 Candida Lipase B 20 1.4.2.5 Amino Acid Dehydrogenase 20 1.4.2.6 Glycosidases 21 1.4.3 Engineered (Unnatural) Reactions 21 1.5 New Trends and Technologies in Biocatalysis 21 1.5.1 Flow Biocatalysis and New Technologies 21 1.5.1.1 What Is Flow Biocatalysis? 21 1.5.1.2 How Does Flow Biocatalysis Work? 21 1.5.1.3 When Is a Flow Process More Beneficial for a Specific Transformation? 23 1.5.1.4 Should One Implement Every Enzymatic Reaction in Flow? 23 1.5.2 Enzyme Engineering 24 1.5.3 Photobiocatalysis 25 1.6 Flow Chart to Biocatalysis 25 1.7 Case Study: Setting up a Biotransformation 27 1.8 Concluding Remarks 31 Additional Resources 31 References 31 2 Introduction to Photochemistry for the Synthetic Chemist 37; Stefano Protti, Davide Ravelli, and Maurizio Fagnoni Glossary 37 2.1 Introduction 38 2.1.1 Light to Make Your Synthesis Greener 38 2.1.2 A Way to Overcome HOMO/LUMO Interactions 39 2.2 How to Plan a Photochemical Synthesis 45 2.2.1 The Choice of the Solvent 45 2.2.2 Concentration of the Absorbing Species 47 2.2.3 The Reaction Vessel 48 2.2.4 Light Sources 48 2.2.4.1 Low- Pressure Mercury Arcs 49 2.2.4.2 Medium- and High- Pressure Mercury Arcs 50 2.2.4.3 Other Light Sources 50 2.2.5 From Batch to Flow Conditions 52 2.2.6 Preparation of the Sample 54 2.2.7 Safety Equipment 54 2.3 Selected Applications of Photochemical/Photocatalyzed Reactions 55 2.3.1 Reactions Involving the C═C Double Bond 55 2.3.2 Reactions Involving the C═O Double Bond 58 2.3.3 Reactions Involving a Photoinduced Homolysis 60 2.3.4 Reactions Involving Singlet Oxygen 62 2.3.5 Reactions Involving a Photocatalytic Step 62 2.4 Conclusions 67 Acknowledgment 67 References 67 3 How to Confidently Become an Electrosynthetic Practitioner 73; Sylvain Charvet, Taline Kerackian, Camille Z. Rubel, and Julien C. Vantourout Glossary 73 Abbreviations 76 3.1 Introduction 77 3.2 General Definition of Organic Electrosynthesis 78 3.3 Why is Organic Electrosynthesis Used? 78 3.4 How is Organic Electrosynthesis Performed? 78 3.5 Where to Start with Electrosynthesis? 79 Selected General Reviews 79 Selected General Guides 79 3.6 Electrasyn 2.0 80 3.6.1 Machine and Consumables 80 3.6.1.1 Opening the IKA ElectraSyn 2.0 Box 80 3.6.1.2 Cell (Vial and Cap) 81 3.6.1.3 Electrodes 82 3.6.2 Interface 83 3.6.2.1 Hardware 83 3.6.2.2 Menus 84 3.6.3 How to Set Up the Cell 84 3.6.4 How to Start an Experiment 85 3.6.5 During the Reaction 88 3.6.6 After the Reaction 89 3.7 Case Study 90 3.7.1 Project Overview 90 3.7.2 Optimization of Parameters 92 3.7.2.1 Designing an Electrochemical Experiment 92 3.7.3 Proof of Concept 94 3.7.3.1 Optimization 94 3.7.3.2 Substrate Scope 102 3.8 Conclusion 103 References 103 4 Flow Chemistry 107; Yosuke Ashikari and Aiichiro Nagaki Glossary 107 4.1 Introduction 109 4.1.1 What is Flow Microchemistry 109 4.1.1.1 Reaction Time Controllability 110 4.1.1.2 Fast Mixing 111 4.1.1.3 Temperature Controllability 112 4.1.2 Reactions Enabled by Flow Microreactors 112 4.1.2.1 Competitive Sequential Reactions 112 4.1.2.2 Reactions Mediated by Unstable Intermediates 114 4.1.2.3 Reactions Occurring at the Surface: Two- Phase Reactions, Electrochemical Reactions, and Photoreactions 117 4.1.3 Further Applicability of Flow Microsynthesis 118 4.1.3.1 Scalability 118 4.1.3.2 Safety Operation 118 4.2 General Information for Flow Microreactors 118 4.2.1 Tools and Equipment for Flow Chemistry 119 4.2.1.1 Micromixer 119 4.2.1.2 Tube Reactor 120 4.2.1.3 Pump 120 4.2.1.4 Pre- Cooling Tubes 121 4.2.1.5 PTFE Tubes 121 4.2.2 How to Perform Experiments 122 4.2.2.1 Selection of Reaction Conditions 122 4.2.2.2 Preparation of Reagent Solution 125 4.2.2.3 Preparation for Reactions 126 4.2.2.4 Preparation for Reaction Evaluation 128 4.2.2.5 Cleaning Up 129 4.3 Case Studies 129 4.3.1 Competitive Sequential Reaction (General Procedure) 129 4.3.1.1 Preparation 130 4.3.1.2 Experiment 132 4.3.1.3 Screening of Reaction Conditions 133 4.3.1.4 Analysis 134 4.3.1.5 Clean Up 136 4.3.2 Reactions Mediated by Short- Lived Intermediates 136 4.3.3 Reaction Integration 139 4.4 Further Expertise 142 4.4.1 Reaction Integration 142 4.4.2 Chemoselective Reactions 143 4.4.3 Heterogeneous Catalytic Reactions 143 4.5 Summary and Outlook 144 References 144 5 Reaction Optimization Using Design of Experiments 149; Laura Forfar and Paul Murray Glossary 149 5.1 Introduction 151 5.1.1 How Do We Experiment and DoE Terminology 151 5.1.2 OVAT vs. DoE 153 5.1.2.1 A Simple Chemical Example 153 5.1.3 A Note on Error, Accuracy, and Precision 156 5.2 When and How Can DoE Be Used? 157 5.3 What Information Can I Get from a DoE and How Is It Obtained? 158 5.3.1 Which Factors Are Important? 159 5.3.2 How Are the Models Generated? 161 5.4 What Types of Design Are Available? 164 5.4.1 Screening Designs 164 5.4.1.1 Fr
• Edition: 1st
• Publisher Details: Hoboken : John Wiley & Sons, Inc
• Publication Date: 2023
• Extent: 1 online resource (496 pages)
• Subjects: 547.2; Organic compounds -- Synthesis
• Languages: English
• ISBNs: 9781119855644
• Notes: Note: Description based on CIP data; resource not viewed.
• Access Rights: Legal Deposit; Only available on premises controlled by the deposit library and to one user at any one time; The Legal Deposit Libraries (Non-Print Works) Regulations (UK).
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