Catalytic Cascade Reactions

Name: Catalytic Cascade Reactions
Brand: Wiley
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Peng-Fei Xu Wei Wang(Herausgeber*in)

Wiley (Verlag)

Erschienen am 2. Oktober 2013

440 Seiten

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Inhalt

Intro
Catalytic Cascade Reactions
Copyright
Contents
Contributors
Preface
1 Amine-Catalyzed Cascade Reactions
1.1 Introduction
1.2 Enamine-Activated Cascade Reactions
1.2.1 Enamine-Enamine Cascades
1.2.1.1 Design of Enamine-Enamine Cascades
1.2.1.2 Examples of Enamine-Enamine and Enamine-Enamine Cyclization Cascades
1.2.1.3 Enamine-Enamine in Three-Component Cascades
1.2.1.4 Enamine-Activated Double a-Functionalization
1.2.1.5 Robinson Annulations
1.2.2 Enamine-Iminium Cascades
1.2.2.1 Design of Enamine-Iminium Cascades
1.2.2.2 Examples of [4 + 2] Reactions with Enamine-Activated Dienes
1.2.2.3 Inverse-Electron-Demand [4 + 2] Reactions with Enamine-Activated Dienophiles
1.2.2.4 Enamine-Iminium-Enamine Cascades
1.2.3 Enamine Catalysis Cyclization
1.2.3.1 Design of Enamine-Cyclization Cascade Reactions
1.2.3.2 Enamine-Intermolecular Addition Cascades
1.2.3.3 Enamine-Intramolecular Addition Cascades
1.2.3.4 Enamine-Intramolecular Aldol Cascades
1.3 Iminium-Initiated Cascade Reactions
1.3.1 Design of Iminium-Enamine Cascade Reactions
1.3.2 Iminium-Activated Diels-Alder Reactions
1.3.3 Iminium-Activated Sequential [4+2] Reactions
1.3.4 Iminium-Activated [3+2] Reactions
1.3.5 Iminium-Activated Sequential [3+2] Reactions
1.3.6 Iminium-Activated [2+1] Reactions
1.3.6.1 Iminium-Activated Cyclopropanations
1.3.6.2 Iminium-Activated Epoxidations
1.3.6.3 Iminium-Activated Aziridinations
1.3.7 Iminium-Activated Multicomponent Reactions
1.3.8 Iminium-Activated [3+3] Reactions
1.3.8.1 Iminium-Activated All-Carbon-Centered [3+3] Reactions
1.3.8.2 Imin ium-Activated Hetero-[3+3] Reactions
1.3.9 Other Iminium-Activated Cascade Reactions
1.4 Cycle-Specific Catalysis Cascades
1.5 Other Strategies
1.6 Summary and Outlook
References
2 Brønsted Acid-Catalyzed Cascade Reactions
2.1 Introduction
2.2 Protonic Acid-Catalyzed Cascade Reactions
2.2.1 Mannich Reaction
2.2.2 Pictect-Spengler Reaction
2.2.3 Biginelli Reaction
2.2.4 Povarov Reaction
2.2.5 Reduction Reaction
2.2.6 1,3-Dipolar Cycloaddition
2.2.7 Darzen Reaction
2.2.8 Acyclic Aminal and Hemiaminal Synthesis
2.2.9 Rearrangement Reaction
2.2.10 a, b -Unsaturated Imine-Involved Cyclization Reaction
2.2.11 Alkylation Reaction
2.2.12 Desymmetrization Reaction
2.2.13 Halocyclization
2.2.14 Redox Reaction
2.2.15 Isocyanide-Involved Multicomponent Reaction
2.2.16 Other Protonic Acid-Catalyzed Cascade Reactions
2.3 Chiral Thiourea (Urea)-Catalyzed Cascade Reactions
2.3.1 Neutral Activation
2.3.1.1 Halolactonization
2.3.1.2 Mannich Reaction
2.3.1.3 Michael-Aldol Reaction
2.3.1.4 Michael-Alkylation Reaction
2.3.1.5 Cyano-Involved Michael-Cyclization Reaction
2.3.1.6 Michael-Hemiketalization (Hemiacetalization) Reaction
2.3.1.7 Michael-Henry Reaction
2.3.1.8 Michael-Michael Reaction
2.3.1.9 Petasis Reaction
2.3.1.10 Sulfur Ylide-Involved Michael-Cyclization Reaction
2.3.1.11 a-Isothiocyanato Imide-Involved Cascade Reaction
2.3.1.12 a-Isocyanide-Involved Cascade Reaction
2.3.2 Anion-Binding Catalysis
2.3.2.1 Pictet-Spengler Reaction
2.3.2.2 Other Iminium Ion-Involved Cascade Reaction
2.3.2.3 Oxocarbenium Ion-Involved Cascade Reaction
2.4 Brønsted Acid and Transition Metal Cooperatively Catalyzed Cascade Reactions
2.4.1 Dual Catalysis
2.4.2 Cascade Catalysis
2.4.2.1 Pd(0)/Brønsted Acid System
2.4.2.2 Ruthenium/Brønsted Acid System
2.4.2.3 Au(I)/Brønsted Acid System
2.4.2.4 Other Binary Catalytic Systems
2.5 Conclusions
References
3 Application of Organocatalytic Cascade Reactions in Natural Product Synthesis and Drug Discovery
3.1 Introduction
3.2 Amine-Catalyzed Cascade Reactions in Natural Product Synthesis
3.2.1 Iminium-Ion-Catalyzed Cascade Reactions in Natural Product Synthesis
3.2.2 Cycle-Specific Cascade Catalysis in Natural Product Synthesis
3.2.2.1 Iminium-Enamine Cycle-Specific Cascade Catalysis
3.2.2.2 Enamine (/Dienamine)-Iminium Cycle-Specific Cascade Catalysis
3.2.2.3 More Complex Cycle-Specific Cascade Catalysis
3.3 Brønsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis
3.4 Bifunctional Base/Brønsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis
3.5 Summary and Outlook
References
4 Gold-Catalyzed Cascade Reactions
4.1 Introduction
4.2 Cascade Reactions of Alkynes
4.2.1 Cascade Reactions of Enynes
4.2.1.1 Cascade Reactions of 1,6-Enynes
4.2.1.2 Cascade Reactions of 1,5-Enynes
4.2.1.3 Cascade Reactions of 1,4-Enynes
4.2.1.4 Cascade Reactions of 1,3-Enynes
4.2.1.5 Cascade Reactions of 1,n-Enynes (n & 6)
4.2.2 Cascade Reactions of Propargyl Carboxylates
4.2.3 Cascade Reactions of ortho-Substituted Arylalkynes
4.2.4 Cascade Reactions of Other Alkynes
4.3 Cascade Reactions of Allenes
4.4 Cascade Reactions of Alkenes and Cyclopropenes
4.5 Closing Remarks
References
5 Cascade Reactions Catalyzed by Ruthenium, Iron, Iridium, Rhodium, and Copper
5.1 Introduction
5.2 Ruthenium-Catalyzed Transformations
5.3 Iron-Catalyzed Transformations
5.4 Iridium-Catalyzed Transformations
5.5 Rhodium-Catalyzed Transformations
5.6 Copper-Catalyzed Transformations
5.7 Miscellaneous Catalytic Reactions
5.8 Summary
References
6 Palladium-Catalyzed Cascade Reactions of Alkenes, Alkynes, and Allenes
6.1 Introduction
6.2 Cascade Reactions Involving Alkenes
6.2.1 Double Mizoroki-Heck Reaction Cascade
6.2.2 Cascade Heck Reaction/C-H Activation
6.2.3 Cascade Heck Reaction/Reduction/ Cyclization
6.2.4 Cascade Heck Reaction/Carbonylation
6.2.5 Cascade Heck Reaction/ Suzuki Coupling
6.2.6 Cascade Amino-/Oxopalladation/Carbopalladation Reaction
6.3 Cascade Reactions Involving Alkynes
6.3.1 Cascade Heck Reactions
6.3.2 Cascade Heck/Suzuki Coupling
6.3.3 Cationic Palladium(II)-Catalyzed Cascade Reactions
6.3.4 Cascade Heck Reaction/Stille Coupling
6.3.5 Cascade Heck/Sonogashira Coupling
6.3.6 Cascade Sonogashira Coupling-Cyclization
6.3.7 Cascade Heck and C-H Bond Functionalization
6.3.8 Cascade Reactions Initiated by Oxopalladation
6.3.9 Cascade Reactions Initiated by Aminopalladation
6.3.10 Cascade Reactions Initiated by Halopalladation or Acetoxypalladation
6.3.11 Cascade Reactions of 2-(1-Alkynyl)-alk-2-en-1-ones
6.3.12 Cascade Reactions of Propargylic Derivatives
6.4 Cascade Reactions Involving Allenes
6.4.1 Cascade Reactions of Monoallenes
6.4.2 Cross-Coupling Cyclization of Two Different Allenes
6.5 Summary and Outlook
Acknowledgments
References
7 Use of Transition Metal-Catalyzed Cascade Reactions in Natural Product Synthesis and Drug Discovery
7.1 Introduction
7.2 Palladium-Catalyzed Cascade Reactions in Total Synthesis
7.2.1 Cross-Coupling Reactions
7.2.1.1 Heck Reaction
7.2.1.2 Stille Reaction
7.2.1.3 Suzuki Coupling Reaction
7.2.2 Tsuji-Trost Reaction
7.2.3 Other Palladium-Catalyzed Cascade Reactions in Total Synthesis
7.3 Ruthenium-Catalyzed Cascade Reactions in Total Synthesis
7.4 Gold- and Platinum-Catalyzed Cascade Reactions in Organic Reactions
7.5 Copper- and Rhodium-Catalyzed Cascade Reactions in O rganic Synthesis
7.6 Summary
References
8 Engineering Mono- and Multifunctional Nanocatalysts for Cascade Reactions
8.1 Introduction
8.2 Heterogeneous Monofunctional Nanocatalysts
8.2.1 Metal-Based Monofunctional Nanocatalysts
8.2.2 Metal Oxide-Based Monofunctional Nanocatalysts
8.2.3 Orgamometallic-Based Monofunctional Nanocatalysts
8.2.4 Graphene Oxide-Based Monofunctional Nanocatalysts
8.3 Heterogeneous Multifunctional Nanocatalysts
8.3.1 Acid-Base Combined Multifunctional Nanocatalysts
8.3.2 Metal-Base Combined Multifunctional Nanocatalysts
8.3.3 Organometallic-Base Combined Multifunctional Nanocatalysts
8.3.4 Binary Organometallic-Based Multifunctional Nanocatalysts
8.3.5 Binary Metal-Based Multifunctional Nanocatalysts
8.3.6 Metal-Metal Oxide Combined Multifunctional Nanocatalysts
8.3.7 Organocatalyst-Acid Combined Multifunctional Nanocatalysts
8.3.8 Acid-Base-Metal Combined Multifunctional Nanocatalysts
8.3.9 Triple Enzyme-Based Multifunctional Nanocatalysts
8.4 Conclusions and Perspectives
References
9 Multiple-Catalyst-Promoted Cascade Reactions
9.1 Introduction
9.2 Multiple Metal Catalyst-Promoted Cascade Reactions
9.2.1 Catalytic Systems Involving Palladium
9.2.2 Catalytic Systems Involving Other Metals
9.3 Multiple Organocatalyst-Promoted Cascade Reactions
9.3.1 Catalytic Systems Combining Multiple Amine Catalysts
9.3.2 Catalytic Systems Combining Amine Catalysts and Nucleophilic Carbenes
9.3.3 Catalytic Systems Combining Amine and Hydrogen-Bonding Donor Catalysts
9.3.4 Catalytic Systems Involving Other Organocatalysts
9.4 Metal/Organic Binary Catalytic System-Promoted Cascade Reactions
9.4.1 Catalytic Systems Combining Secondary Amine and Metal Catalysts
9.4.2 Catalytic Systems Combining Brønsted Acid and Metal Catalysts
9.4.3 Catalytic Systems Combining Hydrogen-Bonding Donor and Metal Catalysts
9.4.4 Catalytic Systems Combining Other Organo- and Metal Catalysts
9.5 Summary and Outlook
References
Index

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