Catalytic Cascade Reactions

Ed. by Xu Peng-Fei and Wang Wei

• Gebundenes Buch

Produktbeschreibung

The development of catalytic versions of cascade reactions has become one of the most active and burgeoning reaction areas in organic synthesis. Covering both organocatalysis and transition-metal catalysis for these reactions, Catalytic Cascade Reactions illustrates the versatility and application of cascade reactions for synthesizing valuable compounds, such as drugs and natural products. Highlighting catalytic versus non-catalytic reactions, an important shift in academic and industry practice, the text brings chemists and the organic synthesis community up to speed on the many recent advances in the field.

Produktdetails

• Verlag: Wiley & Sons
• 1. Auflage
• Seitenzahl: 440
• Erscheinungstermin: 11. November 2013
• Englisch
• Abmessung: 236mm x 160mm x 28mm
• Gewicht: 748g
• ISBN-13: 9781118016022
• ISBN-10: 1118016025
• Artikelnr.: 38028260

Autorenporträt

PENG-FEI XU, PhD, is Director of Teaching Affairs and Professor of Chemistry at Lanzhou University and Deputy Director at the State Key Laboratory of Applied Organic Chemistry. Dr. Xu also serves as an Advisory Board member for the Chinese Chemical Society. During his scientific career, he has published more than 130 papers and received numerous honors and awards, most recently the Award of New Century Excellent Talents in Universities of China and the Thieme Journal Award. WEI WANG, PhD, is Professor of Chemistry at the University of New Mexico. Dr. Wang has published more than 160 peer-reviewed papers. He has received several awards, including The Creative Award from University of New Mexico, The Chinese-American Chemistry & Chemical Biology Professors Association Distinguished Junior Faculty Award, and The American Peptide Society Bruce W. Erickson Young Investigator Award.

Inhaltsangabe

Contributors xi Preface xiii 1 Amine-Catalyzed Cascade Reactions 1 Aiguo Song and Wei Wang 1.1 Introduction
2 1.2 Enamine-Activated Cascade Reactions
3 1.2.1 Enamine-Enamine Cascades
3 1.2.2 Enamine-Iminium Cascades
8 1.2.3 Enamine Catalysis Cyclization
19 1.3 Iminium-Initiated Cascade Reactions
21 1.3.1 Design of Iminium-Enamine Cascade Reactions
21 1.3.2 Iminium-Activated Diels-Alder Reactions
22 1.3.3 Iminium-Activated Sequential [4 + 2] Reactions
24 1.3.4 Iminium-Activated [3 + 2] Reactions
25 1.3.5 Iminium-Activated Sequential [3 + 2] Reactions
27 1.3.6 Iminium-Activated [2 + 1] Reactions
30 1.3.7 Iminium-Activated Multicomponent Reactions
35 1.3.8 Iminium-Activated [3 + 3] Reactions
37 1.4 Cycle-Specific Catalysis Cascades
42 1.5 Other Strategies
45 1.6 Summary and Outlook
46 References
46 2 Brønsted Acid-Catalyzed Cascade Reactions 53 Jun Jiang and Liu-Zhu Gong 2.1 Introduction
54 2.2 Protonic Acid-Catalyzed Cascade Reactions
55 2.2.1 Mannich Reaction
55 2.2.2 Pictect-Spengler Reaction
56 2.2.3 Biginelli Reaction
58 2.2.4 Povarov Reaction
59 2.2.5 Reduction Reaction
60 2.2.6 1
3-Dipolar Cycloaddition
61 2.2.7 Darzen Reaction
65 2.2.8 Acyclic Aminal and Hemiaminal Synthesis
66 2.2.9 Rearrangement Reaction
67 2.2.10 a
b-Unsaturated Imine-Involved Cyclization Reaction
69 2.2.11 Alkylation Reaction
69 2.2.12 Desymmetrization Reaction
70 2.2.13 Halocyclization
71 2.2.14 Redox Reaction
72 2.2.15 Isocyanide-Involved Multicomponent Reaction
73 2.2.16 Other Protonic Acid-Catalyzed Cascade Reactions
75 2.3 Chiral Thiourea (Urea)-Catalyzed Cascade Reactions
75 2.3.1 Neutral Activation
76 2.3.2 Anion-Binding Catalysis
99 2.4 Brønsted Acid and Transition Metal Cooperatively Catalyzed Cascade Reactions
104 2.4.1 Dual Catalysis
105 2.4.2 Cascade Catalysis
108 2.5 Conclusions
116 References
117 3 Application of Organocatalytic Cascade Reactions in Natural Product Synthesis and Drug Discovery 123 Yao Wang and Peng-Fei Xu 3.1 Introduction
123 3.2 Amine-Catalyzed Cascade Reactions in Natural Product Synthesis
125 3.2.1 Iminium-Ion-Catalyzed Cascade Reactions in Natural Product Synthesis
125 3.2.2 Cycle-Specific Cascade Catalysis in Natural Product Synthesis
129 3.3 Brønsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis
137 3.4 Bifunctional Base/Brønsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis
139 3.5 Summary and Outlook
140 References
142 4 Gold-Catalyzed Cascade Reactions 145 Yanzhao Wang and Liming Zhang 4.1 Introduction
145 4.2 Cascade Reactions of Alkynes
147 4.2.1 Cascade Reactions of Enynes
147 4.2.2 Cascade Reactions of Propargyl Carboxylates
156 4.2.3 Cascade Reactions of ortho-Substituted Arylalkynes
161 4.2.4 Cascade Reactions of Other Alkynes
165 4.3 Cascade Reactions of Allenes
170 4.4 Cascade Reactions of Alkenes and Cyclopropenes
173 4.5 Closing Remarks
174 References
174 5 Cascade Reactions Catalyzed by Ruthenium
Iron
Iridium
Rhodium
and Copper 179 Yanguang Wang and Ping Lu 5.1 Introduction
179 5.2 Ruthenium-Catalyzed Transformations
180 5.3 Iron-Catalyzed Transformations
185 5.4 Iridium-Catalyzed Transformations
191 5.5 Rhodium-Catalyzed Transformations
194 5.6 Copper-Catalyzed Transformations
202 5.7 Miscellaneous Catalytic Reactions
215 5.8 Summary
219 References
219 6 Palladium-Catalyzed Cascade Reactions of Alkenes
Alkynes
and Allenes 225 Hongyin Gao and Junliang Zhang 6.1 Introduction
226 6.2 Cascade Reactions Involving Alkenes
226 6.2.1 Double Mizoroki-Heck Reaction Cascade
226 6.2.2 Cascade Heck Reaction/C-H Activation
227 6.2.3 Cascade Heck Reaction/Reduction/Cyclization
230 6.2.4 Cascade Heck Reaction/Carbonylation
231 6.2.5 Cascade Heck Reaction/Suzuki Coupling
232 6.2.6 Cascade Amino-/Oxopalladation/Carbopalladation Reaction
234 6.3 Cascade Reactions Involving Alkynes
237 6.3.1 Cascade Heck Reactions
238 6.3.2 Cascade Heck/Suzuki Coupling
238 6.3.3 Cationic Palladium(II)-Catalyzed Cascade Reactions
239 6.3.4 Cascade Heck Reaction/Stille Coupling
241 6.3.5 Cascade Heck/Sonogashira Coupling
243 6.3.6 Cascade Sonogashira Coupling-Cyclization
244 6.3.7 Cascade Heck and C-H Bond Functionalization
247 6.3.8 Cascade Reactions Initiated by Oxopalladation
253 6.3.9 Cascade Reactions Initiated by Aminopalladation
256 6.3.10 Cascade Reactions Initiated by Halopalladation or Acetoxypalladation
259 6.3.11 Cascade Reactions of 2-(1-Alkynyl)-alk-2-en-1-ones
263 6.3.12 Cascade Reactions of Propargylic Derivatives
263 6.4 Cascade Reactions Involving Allenes
264 6.4.1 Cascade Reactions of Monoallenes
264 6.4.2 Cross-Coupling Cyclization of Two Different Allenes
274 6.5 Summary and Outlook
276 Acknowledgments
277 References
277 7 Use of Transition Metal-Catalyzed Cascade Reactions in Natural Product Synthesis and Drug Discovery 283 Peng-Fei Xu and Hao Wei 7.1 Introduction
283 7.2 Palladium-Catalyzed Cascade Reactions in Total Synthesis
284 7.2.1 Cross-Coupling Reactions
284 7.2.1.1 Heck Reaction
284 7.2.1.2 Stille Reaction
291 7.2.1.3 Suzuki Coupling Reaction
297 7.2.2 Tsuji-Trost Reaction
301 7.2.3 Other Palladium-Catalyzed Cascade Reactions in Total Synthesis
303 7.3 Ruthenium-Catalyzed Cascade Reactions in Total Synthesis
305 7.4 Gold-and Platinum-Catalyzed Cascade Reactions in Organic Reactions
318 7.5 Copper-and Rhodium-Catalyzed Cascade Reactions in Organic Synthesis
322 7.6 Summary
326 References
326 8 Engineering Mono-and Multifunctional Nanocatalysts for Cascade Reactions 333 Hexing Li and Fang Zhang 8.1 Introduction
334 8.2 Heterogeneous Monofunctional Nanocatalysts
335 8.2.1 Metal-Based Monofunctional Nanocatalysts
335 8.2.2 Metal Oxide-Based Monofunctional Nanocatalysts
340 8.2.3 Orgamometallic-Based Monofunctional Nanocatalysts
340 8.2.4 Graphene Oxide-Based Monofunctional Nanocatalysts
343 8.3 Heterogeneous Multifunctional Nanocatalysts
344 8.3.1 Acid-Base Combined Multifunctional Nanocatalysts
344 8.3.2 Metal-Base Combined Multifunctional Nanocatalysts
349 8.3.3 Organometallic-Base Combined Multifunctional Nanocatalysts
349 8.3.4 Binary Organometallic-Based Multifunctional Nanocatalysts
350 8.3.5 Binary Metal-Based Multifunctional Nanocatalysts
352 8.3.6 Metal-Metal Oxide Combined Multifunctional Nanocatalysts
353 8.3.7 Organocatalyst-Acid Combined Multifunctional Nanocatalysts
353 8.3.8 Acid-Base-Metal Combined Multifunctional Nanocatalyst
356 8.3.9 Triple Enzyme-Based Multifunctional Nanocatalysts
356 8.4 Conclusions and Perspectives
359 References
360 9 Multiple-Catalyst-Promoted Cascade Reactions 363 Peng-Fei Xu and Jun-Bing Ling 9.1 Introduction
363 9.2 Multiple Metal Catalyst-Promoted Cascade Reactions
364 9.2.1 Catalytic Systems Involving Palladium
365 9.2.2 Catalytic Systems Involving Other Metals
368 9.3 Multiple Organocatalyst-Promoted Cascade Reactions
370 9.3.1 Catalytic Systems Combining Multiple Amine Catalysts
371 9.3.2 Catalytic Systems Combining Amine Catalysts and Nucleophilic Carbenes
380 9.3.3 Catalytic Systems Combining Amine and Hydrogen-Bonding Donor Catalysts
385 9.3.4 Catalytic Systems Involving Other Organocatalysts
390 9.4 Metal/Organic Binary Catalytic System-Promoted Cascade Reactions
394 9.4.1 Catalytic Systems Combining Secondary Amine and Metal Catalysts
394 9.4.2 Catalytic Systems Combining Brønsted Acid and Metal Catalysts
404 9.4.3 Catalytic Systems Combining Hydrogen-Bonding Donor and Metal Catalysts
411 9.4.4 Catalytic Systems Combining Other Organo-and Metal Catalysts
413 9.5 Summary and Outlook
415 References
415 Index 419