Microwaves in Organic Synthesis (2006)

Volume 1. Preface. About European Cooperation in COST Chemistry Programs. List of Authors. 1 Microwave-Material Interactions and Dielectric Properties, Key Ingredients for Mastery of Chemical Microwave Processes (Didier Stuerga). 1.1 Fundamentals of Microwave-Matter Interactions. 1.2 Key Ingredients for Mastery of Chemical Microwave Processes. References. 2 Development and Design of Laboratory and Pilot Scale Reactors for Microwave-assisted Chemistry (Bernd Ondruschka, Werner Bonrath, and Didier Stuerga). 2.1 Introduction. 2.2 Basic Concepts for Reactions and Reactors in Organic Synthesis. 2.3 Methods for Enhancing the Rates of Organic Reactions. 2.4 Microwave-assisted Organic Syntheses (MAOS). 2.5 Commercial Microwave Reactors - Market Overview. 2.6 Selected Equipment and Applications. 2.7 Qualification and Validation of Reactors and Results. 2.8 Conclusion and Future. References. 3 Roles of Pressurized Microwave Reactors in the Development of Microwaveassisted Organic Chemistry (Thach Le Ngoc, Brett A. Roberts, and Christopher R. Strauss). 3.1 Introduction. 3.2 Toward Dedicated Microwave Reactors. 3.3 Applications of the New Reactors. 3.4 Commercial Release of MBRs and CMRs. 3.5 Advantages of Pressurized Microwave Reactors. 3.6 Applications. 3.7 Effect of the Properties of Microwave Heating on the Scale-up of Methods in Pressurized Reactors. 3.8 Software Technology for Translation of Reaction Conditions. 3.9 Conclusion. Acknowledgments. References. 4 Nonthermal Effects of Microwaves in Organic Synthesis (Laurence Perreux and Andre Loupy). 4.1 Introduction. 4.2 Origin of Microwave Effects. 4.3 Specific Nonthermal Microwave Effects. 4.4 Effects of the Medium. 4.5 Effects Depending on Reaction Mechanisms. 4.6 Effects Depending on the Position of the Transition State Along the Reaction Coordinates. 4.7 Effects on Selectivity. 4.8 Some Illustrative Examples. 4.9 Concerning the Absence of Microwave Effects. 4.10 Conclusions: Suitable Conditions for Observation of Specific MW Effects. References. 5 Selectivity Under the Action of Microwave Irradiation (Antonio de la Hoz, Angel Diaz-Ortiz, and Andres Moreno). 5.1 Introduction. 5.2 Selective Heating. 5.3 Modification of Chemoselectivity and Regioselectivity. 5.4 Modification of Stereo and Enantioselectivity. 5.5 Conclusions. Acknowledgments. References. 6 Microwaves and Phase-transfer Catalysis (Andre Loupy, Alain Petit, and Dariusz Bogdal). 6.1 Phase-transfer Catalysis. 6.2 Synthetic Applications of Phase-transfer Processes. 6.3 Conclusion. References. 7 Microwaves and Ionic Liquids (Nicholas E. Leadbeater and Hanna M. Torenius). 7.1 Introduction. 7.2 Ionic Liquids in Conjunction with Microwave Activation. 7.2.3 Use of Ionic Liquids and Microwaves in Multicomponent Reactions. 7.2.4 Use of Ionic Liquids as Heating Aids. 7.3 Conclusions. Abbreviations. References. 8 Organic Synthesis Using Microwaves and Supported Reagents (Rajender S. Varma and Yuhong Ju). 8.1 Introduction. 8.2 Microwave-accelerated Solvent-free Organic Reactions. 8.3 Conclusions. References. 9 Microwave-assisted Reactions on Graphite (Thierry Besson, Vale'rie Thiery, and Jacques Dubac). 9.1 Introduction. 9.2 Graphite as a Sensitizer. 9.3 Graphite as Sensitizer and Catalyst. 9.4 Notes. 9.5 Conclusion. References. 10 Microwaves in Heterocyclic Chemistry (Jean Pierre Bazureau, Jack Hamelin, Florence Mongin, and Francoise Texier-Boullet). 10.1 Introduction. 10.2 Microwave-assisted Reactions in Solvents. 10.3 Solvent-free Synthesis. 10.4 Conclusion. References and Notes. Volume 2. 11 Microwaves in Cycloadditions (Khalid Bougrin, Mohamed Soufiaoui, and George Bashiardes). 11.1 Cycloaddition Reactions. 11.2 Reactions with Solvent. 11.3 Reactions under Solvent-free Conditions. 11.4 [4+2] Cycloadditions. 11.5 [3+2] Cycloadditions. 11.6 [2p2] Cycloadditions. 11.7 Other Cycloadditions. 11.8 Conclusions. Acknowledgments. References. 12 Microwave-assisted Chemistry of Carbohydrates (Antonino Corsaro, Ugo Chiacchio, Venerando Pistara, and Giovanni Romeo). 12.1 Introduction. 12.2 Protection. 12.3 Deprotection. 12.4 Glycosylation. 12.5 Hydrogenation (Catalytic Transfer Hydrogenation). 12.6 Oxidation. 12.7 Halogenation. 12.8 Stereospecific CxH Bond Activation for Rapid Deuterium Labeling. 12.9 Reaction of Carbohydrates with Amino-derivatized Labels. 12.10 Ferrier (II) Rearrangement to Carbasugars. 12.11 Synthesis of Unsaturated Monosaccharides. 12.12 Synthesis of Dimers and Polysaccharides, and their Derivatives. 12.13 Synthesis of Heterocycles and Amino Acids. 12.14 Enzymatic Reactions. 12.15 Conclusion. References. 13 Microwave Catalysis in Organic Synthesis (Milan Hajek). 13.1 Introduction. 13.2 Preparation of Heterogeneous Catalysts. 13.3 Microwave Activation of Catalytic Reactions. 13.4 Industrial Applications. References. 14 Polymer Chemistry Under the Action of Microwave Irradiation (Dariusz Bogdal and Katarzyna Matras). 14.1 Introduction. 14.2 Synthesis of Polymers Under the Action of Microwave Irradiation. 14.3 Conclusion. References. 15 Microwave-assisted Transition Metal-catalyzed Coupling Reactions (Kristofer Olofsson, Peter Nilsson, and Mats Larhed). 15.1 Introduction. 15.2 Cross-coupling Reactions. 15.3 Arylation of C, N, O, S, P and Halogen Nucleophiles. 15.4 The Heck Reaction. 15.5 Carbonylative Coupling Reactions. 15.6 Summary. Acknowledgment. References. 16 Microwave-assisted Combinatorial and High-throughput Synthesis (Alexander Stadler and C. Oliver Kappe). 16.1 Solid-phase Organic Synthesis. 16.2 Soluble Polymer-supported Synthesis. 16.3 Fluorous-phase Organic Synthesis. 16.4 Polymer-supported Reagents. 16.5 Polymer-supported Catalysts. 16.6 Polymer-supported Scavengers. 16.7 Conclusion. References. 17 Multicomponent Reactions Under Microwave Irradiation Conditions (Tijmen de Boer, Alessia Amore, and Romano V.A. Orru). 17.1 Introduction. 17.2 Nitrogen-containing Heterocycles. 17.3 Oxygen-containing Heterocycles. 17.4 Other Ring Systems. 17.5 Linear Structures. 17.6 Conclusions and Outlook. References. 18 Microwave-enhanced Radiochemistry (John R. Jones and Shui-Yu Lu). 18.1 Introduction. 18.2 Microwave-enhanced Tritiation Reactions. 18.3 Microwave-enhanced Detritiation Reactions. 18.4 Microwave-enhanced PET Radiochemistry. 18.5 Conclusion. Acknowledgments. References. 19 Microwaves in Photochemistry (Petr Klan and Vladimir Cirkva). 19.1 Introduction. 19.2 Ultraviolet Discharge in Electrodeless Lamps. 19.3 Photochemical Reactor and Microwaves. 19.4 Interactions of Ultraviolet and Microwave Radiation with Matter. 19.5 Photochemical Reactions in the Microwave Field. 19.6 Applications. 19.7 Concluding Remarks. Acknowledgments. References. 20 Microwave-enhanced Solid-phase Peptide Synthesis (Jonathan M. Collins and Michael J. Collins). 20.1 Introduction. 20.2 Solid-phase Peptide Synthesis. 20.3 Conclusion. 20.4 Future Trends. Abbreviations. References. 21 Application of Microwave Irradiation in Fullerene and Carbon Nanotube Chemistry (Fernando Langa and Pilar de la Cruz). 21.1 Fullerenes Under the Action of Microwave Irradiation. 21.2 Microwave Irradiation in Carbon Nanotube Chemistry. 21.3 Conclusions. References. 22 Microwave-assisted Extraction of Essential Oils (Farid Chemat and Marie-Elisabeth Lucchesi). 22.1 Introduction. 22.2 Essential Oils: Composition, Properties, and Applications. 22.3 Essential Oils: Conventional Recovery Methods. 22.4 Microwave Extraction Techniques. 22.5 Importance of the Extraction Step. 22.6 Solvent-free Microwave Extraction: Concept, Application, and Future. 22.7 Solvent-free Microwave Extraction: Specific Effects and Proposed Mechanisms. 22.8 Conclusions. References. Index.