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Produktbild: Catalytic Cascade Reactions

Catalytic Cascade Reactions

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Beschreibung

Produktdetails

Einband

Gebundene Ausgabe

Erscheinungsdatum

11.11.2013

Herausgeber

Peng-Fei Xu + weitere

Verlag

John Wiley & Sons Inc

Seitenzahl

440

Maße (L/B/H)

23,6/16/2,8 cm

Gewicht

744 g

Auflage

1. Auflage

Sprache

Englisch

ISBN

978-1-118-01602-2

Beschreibung

Produktdetails

Einband

Gebundene Ausgabe

Erscheinungsdatum

11.11.2013

Herausgeber

Verlag

John Wiley & Sons Inc

Seitenzahl

440

Maße (L/B/H)

23,6/16/2,8 cm

Gewicht

744 g

Auflage

1. Auflage

Sprache

Englisch

ISBN

978-1-118-01602-2

Herstelleradresse

Libri GmbH
Europaallee 1
36244 Bad Hersfeld
DE

Email: gpsr@libri.de

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  • Produktbild: Catalytic Cascade Reactions
  • 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