Overview

Demonstrates the advantages of catalytic cascade reactionsfor synthesizing natural products and pharmaceuticals Riding the wave of green chemistry, catalytic cascade reactionshave become one of the most active research areas in organicsynthesis. During a cascade reaction, just one reaction solvent, one workup procedure, and one purification step are needed, thussignificantly increasing synthetic efficiency. Featuring contributions from an international team of pioneersin the field, Catalytic Cascade Reactions demonstrates theversatility and application of these reactions for synthesizingvaluable compounds. The book examines both organocatalysis andtransition-metal catalysis reactions, bringing readers up to datewith the latest discoveries and activities in all major areas ofcatalytic cascade reaction research. Catalytic Cascade Reactions begins with three chaptersdedicated to organocatalytic cascade reactions, exploring amines, Br nsted acids, and the application of organocatalytic cascadereactions in natural product synthesis and drug discovery. Next, the book covers: Gold-catalyzed cascade reactions Cascade reactions catalyzed by ruthenium, iron, iridium, rhodium, and copper Palladium-catalyzed cascade reactions of alkenes, alkynes, andallenes Application of transition-metal catalyzed cascade reactions innatural product synthesis and drug discovery Engineering mono- and multifunctional nanocatalysts for cascadereactions Multiple-catalyst-promoted cascade reactions All chapters are thoroughly referenced, providing quick accessto important original research findings and reviews so that readerscan explore individual topics in greater depth. Drawing together and analyzing published findings scatteredacross the literature, this book provides a single source thatencapsulates our current understanding of catalytic cascadeprocesses. Moreover, it sets the stage for the development of newcatalytic cascade reactions and their applications.

Full Product Details

Author:   Peng-Fei Xu ,  Wei Wang ,  Peng-Fei Xu ,  Wei Wang (The University of Sydney)
Publisher:   John Wiley & Sons Inc
Imprint:   John Wiley & Sons Inc
ISBN:  

9781118356647

ISBN 10:   1118356640
Pages:   440
Publication Date:   30 December 2013
Audience:   Professional and scholarly ,  Professional & Vocational
Format:   Electronic book text
Publisher's Status:   Active
Availability:   In stock  
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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 Bronsted 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 Bronsted 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 Bronsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis, 137 3.4 Bifunctional Base/Bronsted 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 Bronsted 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

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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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