Microwaves in Organic Synthesis E-Book
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- Herausgeber: Wiley-VCH
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
The third edition of the bestselling two-volume reference covers everything you need to know about microwave technology for synthesis
- from the best equipment to nonthermal effects, from solid-support reactions to catalysis. Completely revised and updated with half of the authors completely new to the project, this comprehensive work is clearly divided into two parts on the fundamentals of microwave irradiation, and application of microwaves and synergies with other enabling techniques. Also new to this edition are chapters on on-line monitoring, flow chemistry, combination with ultrasounds and natural products, including multicomponent reactions.
An indispensable source for organic, catalytic, physical, and medicinal chemists.
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Seitenzahl: 1824
Veröffentlichungsjahr: 2013
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Table of Contents
Related Titles
Title Page
Copyright
Contents to Volume 1
Preface
List of Contributors
Part I: Fundamental Aspects of Microwave Irradiation in Organic Chemistry
Chapter 1: Microwave–Materials Interactions and Dielectric Properties: From Molecules and Macromolecules to Solids and Colloidal Suspensions
1.1 Fundamentals of Microwave–Matter Interactions
1.2 Dielectric Properties and Molecular Behavior
1.3 Conclusion
References
Chapter 2: Development and Design of Reactors in Microwave-Assisted Chemistry
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
2.5 Commercial Microwave Reactors
2.6 Selected Equipment and Applications
2.7 Qualification and Validation of Reactors and Results
2.8 Conclusion and the Future
References
Chapter 3: Key Ingredients for Mastery of Chemical Microwave Processes
3.1 The Systemic Approach
3.2 Thermal Dependence of Dielectric Loss
3.3 Electric Field Effects
3.4 Loop Modes or Strange Solutions of Maxwell's Equations
3.5 Hydrodynamic Aspects
3.6 Thermodynamic and Other Effects of Electric Fields
3.7 Athermal and Specific Effects of Electric Field
3.8 The Thermal Path Effect: Anisothermal Conditions
3.9 Hot Spots and Heterogeneous Kinetics
3.10 Conclusion
References
Chapter 4: Nonthermal Effects of Microwaves in Organic Synthesis
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 coordinate
4.7 Effects on Selectivity
4.8 Some Illustrative Examples
4.9 Concerning the Absence of Microwave Effects
4.10 Conclusion: Suitable Conditions for Observation of Specific MW Effects
References
Chapter 5: Selectivity Modifications Under Microwave Irradiation
5.1 Introduction
5.2 Selective Heating
5.3 Modification of Chemoselectivity and Regioselectivity
5.4 Modification of Stereo- and Enantioselectivity
5.5 Conclusion
Acknowledgments
References
Chapter 6: Elucidation of Microwave Effects: Methods, Theories, and Predictive Models
6.1 Introduction
6.2 Thermal Effects
6.3 Non-Thermal Effects
6.4 Conclusion
Acknowledgments
References
Chapter 7: Microwave Susceptors
7.1 Introduction
7.2 Graphite as a Sensitizer
7.3 Graphite as Sensitizer and Catalyst
7.4 The Use of Silicon Carbide Susceptors in Microwave Chemistry
Acknowledgments
References
Chapter 8: Tools for Monitoring Reactions Performed Using Microwave Heating
8.1 Introduction
8.2 Watching Microwave-Heated Reactions in Real Time
8.3 Monitoring Microwave-Heated Reactions Using In Situ Spectroscopic Tools
8.4 Conclusion
References
Chapter 9: Microwave Frequency Effects in Organic Synthesis
9.1 Introduction
9.2 Historical Review of Microwave Frequency Effects in Chemical Reactions
9.3 Microwave Chemical Reaction Apparatus Operating at Various Frequencies
9.4 Frequency Effects and Heating Efficiency in Various Solutions
9.5 Examples of Chemical Reactions Impacted by Microwave Frequency Effects
9.6 Conclusion
Acknowledgments
References
Part II: Applications of Microwave Irradiation
Chapter 10: Organic Synthesis Using Microwaves and Supported Reagents
10.1 Introduction
10.2 Microwave-Accelerated Solvent-Free Organic Reactions
10.3 Protection–Deprotection Reactions
10.4 Condensation Reactions
10.5 Isomerization and Rearrangement Reactions
10.6 Diels–Alder Cycloaddition of a Triazole Ring
10.7 Addition Reactions
10.8 Oxidation Reactions – Oxidation of Alcohols and Sulfides
10.9 Reduction Reactions
10.10 Synthesis of Heterocyclic Compounds
10.11 Miscellaneous Reactions
10.12 Conclusion
References
Chapter 11: Gaseous Reactants in Microwave-Assisted Synthesis
11.1 Introduction
11.2 Liquid-Phase Synthesis
11.3 Wet Air Oxidation
11.4 Gas-Phase Synthesis
11.5 Waste Gas Treatment
11.6 Conclusion and Outlook
References
Chapter 12: Microwaves and Electrochemistry
12.1 Introduction to Microwave Assisted Electrode Processes
12.2 Macroelectrode Processes in the Presence of Microwaves
12.3 Microelectrode Processes in the Presence of Microwaves
12.4 Junction-Electrode Processes in the Presence of Microwaves
12.5 Electrochemical Flow Reactor Processes in the Presence of Microwaves
12.6 Future Trends
References
Chapter 13: The Combined Use of Microwaves and Ultrasound: Methods and Practice
13.1 Introduction
13.2 The Search for the Best Coupling
13.3 Microwave- and Ultrasound-Enhanced Synthesis and Catalysis
13.4 Formation of Advanced Materials
13.5 Conclusion and Future Trends
References
Chapter 14: Microwaves in Photochemistry and Photocatalysis
14.1 Introduction
14.2 UV/Vis Discharges in Electrodeless Lamps
14.3 Microwave Photochemical and Photocatalytic Reactors
14.4 Interactions of UV/Vis and Microwave Radiation with Matter
14.5 Microwave Photochemistry and Photocatalysis
14.6 Applications
14.7 Future Trends
Acknowledgments
References
Title Page
Contents to Volume 2
Preface
List of Contributors
Chapter 15: Microwave-Heated Transition Metal-Catalyzed Coupling Reactions
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 Conclusion
Acknowledgments
References
Chapter 16: Microwaves in Heterocyclic Chemistry
16.1 Introduction
16.2 Microwave-Assisted Synthesis of Four- and Five-Membered Systems with One and More Than Two Heteroatoms
16.3 Six-Membered Systems with One Heteroatom
16.4 Six-Membered Systems with More Than One Heteroatom
16.5 Bicyclic Systems (Six Atoms + Five Atoms) with One, Two, and More Heteroatoms
16.6 Bicyclic Systems (Six Atoms + Six Atoms) with One, Two, and More Heteroatoms
16.7 Seven Membered Heterocycles with Two Heteroatoms: Microwave-Assisted Synthesis of Benzodiazepines and Related Compounds
16.8 Microwave-Assisted Nucleophilic Aromatic Substitution (SNAr)
16.9 Microwaves in Total Synthesis of Bioactive Heterocycles
16.10 Conclusion
Acknowledgments
References
Chapter 17: Microwave-Assisted Cycloaddition Reactions
17.1 Introduction
17.2 Microwave-Assisted [3 + 2]-Cycloaddition Reactions
17.3 Microwave-Assisted [4 + 2]-Cycloaddition Reactions
17.4 Microwave-Assisted [2 + 2]-Cycloaddition Reactions
17.5 Other Microwave-Assisted Cycloaddition Reactions
17.6 Conclusion
Acknowledgments
References
Chapter 18: Microwave-Assisted Heterogeneously Catalyzed Processes
18.1 Introduction
18.2 Acid-Catalyzed Reactions
18.3 Based-Catalyzed Reactions
18.4 Redox Reactions
18.5 Coupling Reactions
18.6 Other Reactions
18.7 Conclusion and Outlook
Acknowledgments
References
Chapter 19: Microwaves in the Synthesis of Natural Products
19.1 Introduction
19.2 Total Synthesis of Various Classes of Natural Products
19.3 Total Synthesis of Various Classes of Alkaloids
19.4 Synthesis of Analogs of Natural Products
19.5 Synthesis of Building Blocks (Subunits) for Natural Product
19.6 Conclusion and Overview
References
Chapter 20: Microwave-Enhanced Synthesis of Peptides, Proteins, and Peptidomimetics
20.1 Introduction
20.2 Synthesis Approaches
20.3 Microwave Theory for Peptide Synthesis
20.4 Nα-Amino Protection Strategies
20.5 Amide Bond Formation
20.6 Modified Peptides
20.7 Non-Natural Peptidomimetics
20.8 Resin Cleavage
20.9 Recommended Protocols
20.10 Conclusion
20.11 Abbreviations
Acknowledgment
References
Chapter 21: A Journey into Recent Microwave-Assisted Carbohydrate Chemistry
21.1 Introduction
21.2 Acylation
21.3 Glycosylation
21.4 Halogenation-Dehalogenation
21.5 Sulfation
21.6 Anomerization
21.7 Synthesis of Sugar Derivatives
21.8 Synthesis of Biologically and Pharmacological Active Compounds
21.9 Synthesis of Heterocycles
21.10 Synthesis of Phosphorus Compounds
21.11 Synthesis of Nanostructured Materials
21.12 Conclusion
Acknowledgment
References
Chapter 22: Polymer Chemistry Under Microwave Irradiation
22.1 Introduction
22.2 Synthesis of Polymers Under Microwave Irradiation
22.3 Conclusion
References
Chapter 23: Application of Microwave Irradiation in Carbon Nanostructures
23.1 Fullerenes Under Microwave Irradiation
23.2 Microwave Irradiation in Carbon Nanotubes
23.3 Microwave Irradiation in Other Carbon Nanoforms
23.4 Conclusion
References
Chapter 24: Microwave-Assisted Multicomponent Reactions in the Synthesis of Heterocycles
24.1 Introduction
24.2 Nitrogen Heterocycles
24.3 Oxygen-Containing Rings
24.4 Sulfur-Containing Rings
24.5 Oxygen- and Nitrogen-Containing Rings
24.6 Carbacycles
24.7 Multiple Ring Systems
24.8 Conclusion
24.9 Abbreviations
References
Chapter 25: Microwave-Assisted Continuous Flow Organic Synthesis (MACOS)
25.1 Introduction
25.2 Equipment
25.3 MACOS in Homogeneous System
25.4 MACOS in Heterogeneous System
25.5 Conclusion and Outlook
References
Index
Related Titles
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The Editor
Prof. Antonio de la Hoz
Universidad de Castilla-la Mancha
Facultad de Química
Departamento de Química Orgánica
13071 Ciudad Real
Spain
Dr. André Loupy
Université Paris-Sud
Laboratoire des Réactions Sélectives sur Supports
Batiment 410
91405 Orsay Cedex
France
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© 2012 Wiley-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany
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Contents to Volume 1
Preface
Since the publication of the first edition of this book in 2002, the use of microwaves in organic synthesis has today become a general and useful methodology, with application in almost all kinds of reactions in organic chemistry and also in many other fields of chemistry, not covered in this book.
The two famous pioneering papers from Gedye and Giguere in 1986 are generally considered the beginning of the use of this methodology in organic synthesis. Since then, many authors have contributed to its development and spreading throughout the world. We would highlight the pioneering work of Strauss in Australia, Loupy/Bram and Hamelin in Europe, and Varma in the USA – all of them authors in the present and previous editions of this book. Today, a new generation of very active and highly competent chemists has extended the applications of microwave irradiation and the development of new instruments and methodologies.
The introduction of microwave instruments specially designed for chemistry was one of the milestones in the development of this methodology. Since their introduction, the number of papers dedicated to microwave-assisted organic chemistry has increased exponentially. Thanks to these instruments, careful control of all reaction parameters, temperature, pressure, incident power, and so on, is now possible. In this way, reproducibility of microwave-assisted reactions, the major drawback of this methodology when using domestic-type ovens, was achieved. Moreover, these new instruments were fitted for laboratory work with high security.
This third edition consists of 25 chapters seriously restructured and updated in relation to the previous editions, nine chapters being completely new.
The first part of the book is dedicated to fundamental aspects of microwave irradiation in organic synthesis. First, a revision and description of materials–wave interactions is presented (Chapter 1), including interactions from molecules to macromolecules to solids and colloidal suspensions. Chapter 2 is dedicated to microwave technology and instruments including scale-up, while Chapter 3 is dedicated to the design of microwave-assisted processes. The issue of microwave effects (possibly nonthermal) is discussed in Chapter 4; methods, theories, and predictive models are collected in a new chapter (Chapter 6). The modifications of selectivity under microwave irradiation are reviewed in Chapter 5. Some important aspects of microwave methodology are collected in the new Chapters 7–9 such as the use of microwave susceptors (Chapter 7), methods for monitoring of microwave-assisted reactions (Chapter 8), and the influence of variable frequency in organic chemistry (Chapter 9).
The second part is dedicated to applications of microwave irradiation and its synergic use with other enabling technologies. In this regard, new chapters have been included on microwaves and electrochemistry (Chapter 12), ultrasound (Chapter 13), and flow methodologies (Chapter 25). Revised chapters were prepared on reactions on solid supports (Chapter 10) and photochemistry and photocatalysis under microwaves (Chapter 14). Some classic applications, in which microwave irradiation has afforded spectacular results, have been revised and extended, such as transition metal-catalyzed reactions (Chapter 15), heterocyclic chemistry (Chapter 16), cycloaddition reactions (Chapter 17), carbohydrate chemistry (Chapter 21), and multicomponent reactions (Chapter 24). Applications to solid-phase peptide synthesis (Chapter 20), polymer chemistry (Chapter 22), and carbon nanostructured materials (Chapter 23) have been substantially modified since these very active areas have found many new applications. Finally, new chapters dealing with applications to gaseous reagents (Chapter 11), heterogeneous catalysis (Chapter 18), and the synthesis of natural products (Chapter 19) have been added.
We wish to thank sincerely all our colleagues and friends involved in the realization of this book. We want to express sincerely to them, all eminent specialists, our gratitude for agreeing to devote their competence and time to submitting and reviewing chapters to ensure the success of this book.
We would like especially to dedicate this book to the memory two authors in the first and second editions recently deceased: Professor Jack Hamelin, our “Jack Pote” (in French, pote means friend), and Mohamed Soufiaoui, our “Great Friend.” Chapters 16 and 17 are dedicated to them. They were excellent friends as well as extraordinary researchers with important dedication and engagement with their respective universities and countries (France and Morocco).
Antonio de la Hoz and André Loupy
List of Contributors
Part I
Fundamental Aspects of Microwave Irradiation in Organic Chemistry
Chapter 1
Microwave–Materials Interactions and Dielectric Properties: From Molecules and Macromolecules to Solids and Colloidal Suspensions
Didier Stuerga
1.1 Fundamentals of Microwave–Matter Interactions
The objective of the first part of the book is to explain in a chemically intelligible fashion the physical origin of microwave–matter interactions and in this chapter especially the theory of dielectric relaxation of polar molecules. This third revised edition contains approximately 30% of new material in order to cover a large area of reaction media able to be heated by microwave irradiation. Colloidal suspensions and highly functional polymers are now included. The accounts presented in the various chapters are intended to be illustrative rather than exhaustive. They are planned to serve as introductions to the various aspect of interest for comprehensive microwave heating. In this sense, the treatment is selective and to some extent arbitrary. Hence the reference lists contain historical papers and valuable reviews to which the reader anxious to pursue further particular aspects should certainly turn.
It is the author's conviction, confirmed over many years of teaching experience, that it is much safer – at least for those who rate not trained physicists – to deal intelligently with oversimplified models than to use sophisticated methods which require experience before becoming productive. However, and in response to comments on the first and second editions, the author has given more technical comments in relation to a better understanding of concepts and ideas. These paragraphs can be omitted depending on the level of experience of the reader. They are preceded by two type of logo: TOOLS and CONCEPTS.
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