ISBN-10:
1118016025
ISBN-13:
9781118016022
Pub. Date:
11/04/2013
Publisher:
Wiley
Catalytic Cascade Reactions / Edition 1

Catalytic Cascade Reactions / Edition 1

by Peng-Fei Xu, Wei Wang
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Product Details

ISBN-13: 9781118016022
Publisher: Wiley
Publication date: 11/04/2013
Pages: 440
Product dimensions: 6.30(w) x 9.30(h) x 1.10(d)

About the Author

PENG-FEI XU, PhD, is Director of Teaching Affairs andProfessor of Chemistry at Lanzhou University and Deputy Director atthe State Key Laboratory of Applied Organic Chemistry. Dr. Xu alsoserves as an Advisory Board member for the Chinese ChemicalSociety. During his scientific career, he has published more than130 papers and received numerous honors and awards, most recentlythe Award of New Century Excellent Talents in Universities of Chinaand the Thieme Journal Award.

WEI WANG, PhD, is Professor of Chemistry at theUniversity of New Mexico. Dr. Wang has published more than 160peer-reviewed papers. He has received several awards, including TheCreative Award from University of New Mexico, The Chinese-AmericanChemistry & Chemical Biology Professors AssociationDistinguished Junior Faculty Award, and The American PeptideSociety Bruce W. Erickson Young Investigator Award.

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Table of Contents

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 Reactions53
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 CooperativelyCatalyzed 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 NaturalProduct Synthesis and Drug Discovery 123
Yao Wang and Peng-Fei Xu

3.1 Introduction, 123

3.2 Amine-Catalyzed Cascade Reactions in Natural ProductSynthesis, 125

3.2.1 Iminium-Ion-Catalyzed Cascade Reactions in Natural ProductSynthesis, 125

3.2.2 Cycle-Specific Cascade Catalysis in Natural ProductSynthesis, 129

3.3 Brønsted Acid–Catalyzed Cascade Reactions inNatural Product Synthesis, 137

3.4 Bifunctional Base/Brønsted Acid–Catalyzed CascadeReactions 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 orAcetoxypalladation, 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 Reactionsin 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 TotalSynthesis, 303

7.3 Ruthenium-Catalyzed Cascade Reactions in Total Synthesis,305

7.4 Gold-and Platinum-Catalyzed Cascade Reactions in OrganicReactions, 318

7.5 Copper-and Rhodium-Catalyzed Cascade Reactions in OrganicSynthesis, 322

7.6 Summary, 326

References, 326

8 Engineering Mono-and Multifunctional Nanocatalysts forCascade 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 MultifunctionalNanocatalysts, 349

8.3.4 Binary Organometallic–Based MultifunctionalNanocatalysts, 350

8.3.5 Binary Metal–Based Multifunctional Nanocatalysts,352

8.3.6 Metal–Metal Oxide Combined MultifunctionalNanocatalysts, 353

8.3.7 Organocatalyst–Acid Combined MultifunctionalNanocatalysts, 353

8.3.8 Acid–Base–Metal Combined MultifunctionalNanocatalyst, 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 andNucleophilic Carbenes, 380

9.3.3 Catalytic Systems Combining Amine and Hydrogen-BondingDonor Catalysts, 385

9.3.4 Catalytic Systems Involving Other Organocatalysts, 390

9.4 Metal/Organic Binary Catalytic System–Promoted CascadeReactions, 394

9.4.1 Catalytic Systems Combining Secondary Amine and MetalCatalysts, 394

9.4.2 Catalytic Systems Combining Brønsted Acid and MetalCatalysts, 404

9.4.3 Catalytic Systems Combining Hydrogen-Bonding Donor andMetal Catalysts, 411

9.4.4 Catalytic Systems Combining Other Organo-and MetalCatalysts, 413

9.5 Summary and Outlook, 415

References, 415

Index 419

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