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Book Details
Abstract
There is a growing interest in the development of sustainable processes for the synthesis of pharmaceuticals and this book bridges the divide between industrial examples and the fundamental chemistry. It explains the basic principles of using transition metal catalysis with several green approaches for the synthesis of pharmaceuticals. The topic is an important one for green chemistry and the chapters in this book on hydroformylation, green oxidation and olefin metathesis will also be of interest to both medicinal and organic chemists.
Written by leading experts in the field, it provides a valuable and easy tool for scientists and industrialists who require information regarding this topic.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Preface | vii | ||
| Contents | ix | ||
| Chapter 1 Introduction | 1 | ||
| 1.1 Introduction | 1 | ||
| References | 4 | ||
| Chapter 2 Transition Metals in Greener Pharmaceutical Chemistry | 5 | ||
| 2.1 Transition Metals in Greener Pharmaceutical Chemistry | 5 | ||
| References | 7 | ||
| Chapter 3 Sustainable Synthesis of Pharmaceuticals Using Alternative Techniques: Microwave, Sonochemistry and Mechanochemistry | 8 | ||
| 3.1 Introduction | 8 | ||
| 3.2 Metrics | 10 | ||
| 3.3 Microwave | 21 | ||
| 3.4 Sonochemistry | 29 | ||
| 3.5 Mechanochemistry | 32 | ||
| 3.6 Conclusion | 37 | ||
| Acknowledgements | 37 | ||
| References | 37 | ||
| Chapter 4 Carbonylation Reactions in the Synthesis of Pharmaceutically Active Compounds | 40 | ||
| 4.1 Introduction | 40 | ||
| 4.2 Hydroalkoxycarbonylation of Alkenes | 43 | ||
| 4.3 Carbonylation of Aryl/Alkenyl Halides | 44 | ||
| 4.3.1 Aminocarbonylation Reactions | 45 | ||
| 4.3.2 Alkoxy-and Hydroxycarbonylations | 50 | ||
| 4.3.3 Carbonylative Coupling Reactions | 52 | ||
| 4.3.4 The Use of CO Equivalents | 54 | ||
| 4.3.5 Industrial Applications | 55 | ||
| 4.4 Oxidative Carbonylation Reactions | 56 | ||
| 4.5 Conclusion and Outlook | 61 | ||
| Acknowledgements | 61 | ||
| References | 61 | ||
| Chapter 5 Applications of Catalytic Hydroformylation in the Synthesis of Biologically Relevant Synthons and Drugs | 66 | ||
| 5.1 Introduction | 66 | ||
| 5.2 Hydroformylation Catalysts—A Historical Perspective | 68 | ||
| 5.3 Hydroformylation with Alternative Catalytic Systems | 75 | ||
| 5.4 Catalytic Hydroformylation in the Synthesis of Biologically Active Molecules: Selected Examples | 77 | ||
| 5.4.1 Enantioselective and Diastereoselective Hydroformylation in Drug Synthesis | 85 | ||
| 5.5 Conclusion and Future Perspective | 96 | ||
| Acknowledgements | 99 | ||
| References | 99 | ||
| Chapter 6 Transfer Hydrogenation with Non-toxic Metals for Drug Synthesis | 105 | ||
| 6.1 Introduction | 105 | ||
| 6.2 Transfer Hydrogenation | 106 | ||
| 6.2.1 Mechanistic Overview of Transfer Hydrogenation of Ketones | 109 | ||
| 6.2.2 Transfer Hydrogenation with Cheap Metals | 112 | ||
| 6.2.3 Asymmetric Transfer Hydrogenation in the Synthesis of Bioactive Molecules | 116 | ||
| 6.3 Borrowing Hydrogen Methodology | 122 | ||
| 6.4 Conclusion | 135 | ||
| Acknowledgements | 135 | ||
| References | 135 | ||
| Chapter 7 Green Metal-catalysed Synthesis of Pharmaceutically Useful Asymmetric Epoxides and Sulfoxides | 139 | ||
| 7.1 Epoxidation and Sulfoxidation: Introduction | 139 | ||
| 7.2 Asymmetric Transition Metal-catalysed Epoxidation of Olefins | 141 | ||
| 7.2.1 The Katsuki–Sharpless Asymmetric Epoxidation of Allylic Alcohols | 141 | ||
| 7.2.2 The Jacobsen–Katsuki Epoxidation with M(salen) Complexes | 155 | ||
| 7.2.3 M(bis-hydroxamic acid)-catalysed Epoxidations | 170 | ||
| 7.2.4 M(aminopyridine)-catalysed Epoxidations | 172 | ||
| 7.3 Transition Metal-catalysed Asymmetric Sulfoxidation | 174 | ||
| 7.3.1 Asymmetric Sulfoxidation with Sharpless-type Catalysts | 175 | ||
| 7.3.2 Asymmetric Sulfoxidation with Jacobsen–Katsuki-type Catalysts | 182 | ||
| 7.3.3 Asymmetric Sulfoxidation with M(bis-hydroxamic) Catalysts | 182 | ||
| 7.3.4 Catalytic ASO Processes Using Environmentally Sustainable O2 as TO | 182 | ||
| 7.3.5 Catalytic ASO Processes Using Environmentally Sustainable H2O2 as TO | 183 | ||
| 7.3.6 M(salen), M(salan) and M(salalen) Sulfoxidation with H2O2 as TO | 185 | ||
| 7.4 Conclusion | 187 | ||
| References | 188 | ||
| Chapter 8 C–C Bond Formation in the Sustainable Synthesis of Pharmaceuticals | 193 | ||
| 8.1 Introduction | 193 | ||
| 8.2 C–C Coupling Reactions | 196 | ||
| 8.2.1 Suzuki–Miyaura Coupling | 196 | ||
| 8.2.2 Negishi and Stille Couplings | 198 | ||
| 8.2.3 Sonogashira Coupling | 200 | ||
| 8.2.4 Heck Coupling | 200 | ||
| 8.2.5 Decarboxylative C–C Coupling | 202 | ||
| 8.2.6 The Kumada–Corriu Coupling | 203 | ||
| 8.2.7 The α-Arylation of Enolates | 205 | ||
| 8.2.8 The Hayashi–Miyaura Reaction | 207 | ||
| 8.2.9 Tsuji–Trost Allylation | 210 | ||
| 8.2.10 Aromatic Cyanation | 213 | ||
| 8.2.11 Nozaki–Hiyama–Kishi Coupling Reaction | 216 | ||
| 8.2.12 C–H Activation | 219 | ||
| 8.3 Conclusion | 224 | ||
| Abbreviations | 224 | ||
| Acknowledgements | 225 | ||
| References | 225 | ||
| Chapter 9 Metal-catalysed Metathesis Reactions for Greener Synthon/Drug Synthesis | 230 | ||
| 9.1 Introduction | 230 | ||
| 9.2 Mechanistic Aspects | 232 | ||
| 9.3 Catalysts for Metathesis | 233 | ||
| 9.3.1 Ruthenium Catalysts with Well-defined Structures | 234 | ||
| 9.3.2 Tungsten and Molybdenum Catalysts of Well-defined Structures | 236 | ||
| 9.3.3 Molecular Catalyst Stability | 237 | ||
| 9.3.4 Catalyst Residue Removal | 238 | ||
| 9.4 The Choice of Reaction Conditions | 238 | ||
| 9.5 Selected Examples of Metathesis in (Industrial) Organic Synthesis | 239 | ||
| 9.5.1 Cross Metathesis | 240 | ||
| 9.5.2 Ring-closing Metathesis | 244 | ||
| 9.6 Conclusion | 248 | ||
| Acknowledgements | 251 | ||
| References | 251 | ||
| Chapter 10 Tetravalent Boron-based Therapeutics | 253 | ||
| 10.1 Introduction | 253 | ||
| 10.2 Boron Dipyrromethenes | 254 | ||
| 10.2.1 Structure and Properties | 254 | ||
| 10.2.2 Application in PDT | 256 | ||
| 10.2.3 Structure Modifications | 257 | ||
| 10.2.4 Application in BNCT | 265 | ||
| 10.3 Naturally Occurring Tetravalent Boron Therapeutics | 267 | ||
| 10.3.1 Boromycin | 267 | ||
| 10.3.2 Aplasmomycin A, B and C | 268 | ||
| 10.3.3 Tartrolons | 268 | ||
| 10.3.4 Borophycin | 268 | ||
| 10.4 Naturally-inspired Boron Therapeutics | 271 | ||
| 10.4.1 Borinate Ester Derivatives | 271 | ||
| 10.4.2 Boronate Ester Derivatives | 271 | ||
| 10.4.3 Boroxazolidones | 271 | ||
| 10.4.4 Arylspiroborates | 273 | ||
| 10.5 Conclusion | 274 | ||
| References | 274 | ||
| Subject Index | 282 |