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Produktbild: Copper-Mediated Cross-Coupling Reactions

Copper-Mediated Cross-Coupling Reactions

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Beschreibung

Produktdetails

Einband

Gebundene Ausgabe

Erscheinungsdatum

11.11.2013

Verlag

John Wiley & Sons

Seitenzahl

848

Maße (L/B/H)

24.1/16.6/5 cm

Gewicht

1320 g

Auflage

1. Auflage

Sprache

Englisch

ISBN

978-1-118-06045-2

Beschreibung

Rezension

"The book is a key resource for copper chemistry and amust-have, for experts and students alike." ( Angewandte Chemie , 30 May 2014)

Produktdetails

Einband

Gebundene Ausgabe

Erscheinungsdatum

11.11.2013

Verlag

John Wiley & Sons

Seitenzahl

848

Maße (L/B/H)

24.1/16.6/5 cm

Gewicht

1320 g

Auflage

1. Auflage

Sprache

Englisch

ISBN

978-1-118-06045-2

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  • Produktbild: Copper-Mediated Cross-Coupling Reactions
  • FOREWORD xvii

    Stephen L. Buchwald

    PREFACE: COPPER CATALYSIS FROM A HISTORICAL PERSPECTIVE: A LEGACY FROM THE PAST xix

    Gwilherm Evano and Nicolas Blanchard

    CONTRIBUTORS xxxiii

    PART I FORMATION OF C-HETEROATOM BONDS 1

    1 Modern Ullmann-Goldberg Chemistry: Arylation of N-Nucleophiles with Aryl Halides 3
    Yongwen Jiang and Dawei Ma

    1.1 Introduction, 3

    1.2 Arylation of Amines, 4

    1.3 Arylation of Amides, Imides, and Carbamates, 15

    1.4 Arylation of Conjugated N-Heterocycles, 24

    1.5 Synthesis of Anilines by Coupling with Ammonia or Synthetic Equivalents, 32

    1.6 Conclusion and Future Prospects, 37

    References, 37

    2 Ullmann Condensation Today: Arylation of Alcohols and Thiols with Aryl Halides 41
    Anis Tlili and Marc Taillefer

    2.1 Introduction, 41

    2.2 Formation of C-O Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides, 42

    2.3 Formation of C-S Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides, 67

    2.4 Conclusion, 84

    References, 86

    3 Copper-Catalyzed Formation of C-P Bonds with Aryl Halides 93
    Carole Alayrac and Annie-Claude Gaumont

    3.1 Introduction, 93

    3.2 Arylation of Phosphines, 94

    3.3 Arylation of Phosphine Oxides and Phosphites, 98

    3.4 Conclusion, 110

    References, 110

    4 Alternative and Emerging Reagents for the Arylation of Heteronucleophiles 113
    Luc Neuville

    4.1 Introduction, 113

    4.2 Chan-Lam-Evans Coupling: Copper(II)-Promoted Oxidative Aryl Transfer from Arylboron Derivatives, 115

    4.3 Copper-Promoted Aryl Transfer from Metallated Aryl Derivatives (Nonboron), 141

    4.4 Copper-Catalyzed Arylation Reactions Involving Masked S- and N-Nucleophiles, 151

    4.5 Copper-Catalyzed Direct Heterofunctionalization of Aromatic C-H Bonds, 160

    4.6 Conclusion and Future Prospects, 178

    References, 178

    5 Beyond Ullmann-Goldberg Chemistry: Vinylation, Alkynylation, and Allenylation of Heteronucleophiles 187
    Kévin Jouvin and Gwilherm Evano

    5.1 Introduction, 187

    5.2 Copper-Mediated Alkenylation of Heteronucleophiles: Among the Best Routes to Heteroatom-Substituted Alkenes, 189

    5.3 Alkynylation of Heteronucleophiles: The Emergence of General Methods for the Synthesis of Heteroatom-Substituted Alkynes, 219

    5.4 Allenylation of Heteronucleophiles: New Tools for the Synthesis of Allenamides, 232

    5.5 Conclusion and Future Prospects, 233

    References, 234

    6 Aromatic/Vinylic Finkelstein Reaction 239
    Alicia Casitas and Xavi Ribas

    6.1 Introduction, 239

    6.2 Copper-Mediated Halogen Exchange Reactions in Aryl Halides, 241

    6.3 Most Recent Developments and Overview, 247

    References, 249

    7 Insights into the Mechanism of Modern Ullmann-Goldberg Coupling Reactions 253
    Alicia Casitas and Xavi Ribas

    7.1 General View and Key Mechanistic Aspects, 253

    7.2 Oxidation State of Copper Catalysts, 254

    7.3 Identity of the Active Copper(I) Complex, 255

    7.4 Activation Mode of Aryl Halides by Copper Complexes, 261

    7.5 Overview, Conclusions, and Future Prospects, 275

    References, 277

    PART II FORMATION OF C-C BONDS 281

    8 Modern Copper-Catalyzed Hurtley Reaction: Efficient C-Arylation of CH-Acid Derivatives 283
    Irina P. Beletskaya and Alexey Yu. Fedorov

    8.1 Introduction, 283

    8.2 Classical Hurtley Reaction, 285

    8.3 Ligation Effect in Copper-Catalyzed Reactions of Aryl Halides with Carbanions, 286

    8.4 Cascade Reactions Proceeding via a Hurtley Arylation Reaction, 293

    8.5 Mechanism of the Copper-Catalyzed C-Arylation Reactions, 303

    8.6 Concluding Remarks, 308

    References, 308

    9 Copper-Catalyzed Cyanations of Aryl Halides and Related Compounds 313
    Thomas Schareina and Matthias Beller

    9.1 Introduction, 313

    9.2 Modifications and Updates of Classical Cyanation Reactions (Rosenmund-von Braun, Sandmeyer), 315

    9.3 Copper-Catalyzed Cyanations of Aryl Halides, 316

    9.4 Copper-Mediated Oxidative Cyanations, 324

    9.5 Conclusion, 331

    References, 331

    10 Copper-Mediated Aryl-Aryl Bond Formation Leading to Biaryls: A Century after the Ullmann Breakthrough 335
    Yoshihiko Yamamoto

    10.1 Introduction, 335

    10.2 Biaryl Synthesis by Coupling of Aryl Halides and Diazonium Salts, 336

    10.3 Biaryl Synthesis by Coupling of Aryltin, Boron, and Silanes, 347

    10.4 Biaryl Synthesis by Arylation Involving Arene C-H or C-C Bond Fission, 357

    10.5 Biaryl Synthesis by Oxidative Coupling of 2-Naphthols, 376

    10.6 Conclusions and Outlook, 387

    References, 388

    11 Copper-Catalyzed Alkynylation, Alkenylation, and Allylation Reactions of Aryl Derivatives 401
    Ren-Jie Song and Jin-Heng Li

    11.1 Introduction, 401

    11.2 Copper-Catalyzed Alkynylation of Aryl Derivatives, 402

    11.3 Copper-Catalyzed Alkenylation of Aryl Derivatives, 432

    11.4 Copper-Catalyzed Strategies for the Formation of Allyl-Aryl Bonds, 445

    11.5 Conclusion and Outlook, 450

    References, 450

    12 Copper-Catalyzed Alkynylation and Alkenylation Reactions of Alkynyl Derivatives: New Access to Diynes and Enynes 455
    Ruimao Hua

    12.1 Introduction, 455

    12.2 Copper-Catalyzed Synthesis of Symmetrical and Unsymmetrical 1,3-Diynes, 456

    12.3 Copper-Catalyzed Synthesis of 1,4-Diynes, 468

    12.4 Synthesis of 1,3-Enynes by Direct Reaction of Vinyl Halides with Alkynes, 468

    12.5 Synthesis of 1,3-Enynes by Stille-Type Cross-Coupling Reaction, 474

    12.6 Synthesis of 1,3-Enynes by the Suzuki-Miyaura-Type Cross-Coupling Reaction, 476

    12.7 Synthesis of 1,4-Enynes by Allylation Reaction of Terminal Alkynes, 478

    12.8 Conclusion, 480

    References, 480

    13 Copper-Mediated Alkenylation Reaction of Alkenyl Derivatives: A Straightforward Elaboration of 1,3-Dienes 485
    Hao Li, Songbai Liu, and Lanny S. Liebeskind

    13.1 Introduction, 485

    13.2 Symmetrical 1,3-Dienes by Homocoupling Reaction of Vinyl Derivatives, 486

    13.3 Unsymmetrical 1,3-Dienes by Cross-Coupling Reactions, 496

    13.4 Conclusions, 510

    References, 511

    14 Emerging Areas in Copper-Mediated Trifl uoromethylations of Aryl Derivatives: Catalytic and Oxidative Cross-Coupling Processes 515
    Kévin Jouvin, Céline Guissart, Cédric Theunissen, and Gwilherm Evano

    14.1 Introduction, 515

    14.2 Copper-Catalyzed Trifluoromethylation of Aryl Halides: A Long-Lasting Quest Finally Reached, 517

    14.3 Copper-Mediated Oxidative Trifl uoromethylation Reactions, 523

    14.4 Conclusion and Future Prospects, 528

    References, 528

    PART III APPLICATIONS OF COPPER-CATALYZED CROSS-COUPLING REACTIONS: HETEROCYCLES, NATURAL PRODUCTS, PROCESS, AND SUSTAINABLE CHEMISTRY 531

    15 Copper-Mediated Cyclization Reactions: New Entries to Heterocycles 533
    Daoshan Yang and Hua Fu

    15.1 Introduction, 533

    15.2 Cyclization by C-N Bond Formation, 534

    15.3 Cyclization by C-O Bond Formation, 560

    15.4 Cyclization by C-C Bond Formation, 567

    15.5 Copper-Catalyzed Double Cross-Coupling Reactions for the Assembly of Heterocycles, 576

    15.6 Conclusion and Future Prospects, 583

    References, 584

    16 Application of Copper-Mediated C-N Bond Formation in Complex Molecules Synthesis 589
    Jihoon Lee and James S. Panek

    16.1 Introduction, 589

    16.2 Aryl Amination in Complex Molecule Synthesis, 590

    16.3 Aryl Amidation in Complex Molecule Synthesis, 595

    16.4 Arylation of N-Heterocycles in Complex Molecule Synthesis, 601

    16.5 Vinyl Amidation in Complex Molecule Synthesis, 606

    16.6 Alkyne Amidation in Complex Molecule Synthesis, 620

    16.7 Intramolecular C-N Bond Formation in Natural Product Synthesis, 622

    16.8 Summary and Outlook, 637

    References, 638

    17 Natural Products and C-O/C-S Bond-Forming Reactions: Copper Showed the Way 643
    Doron Pappo

    17.1 Introduction, 643

    17.2 Total Synthesis of Naturally Occurring Diaryl Ethers by Arylation of Phenols, 644

    17.3 Intramolecular Diaryl Ether Bond-Forming Reactions, 659

    17.4 Arylation of Alcohols, 666

    17.5 Vinylation of Alcohols, 673

    17.6 Copper-Mediated C-S Bond Formation in Natural Product Synthesis, 675

    17.7 Conclusion and Future Prospects, 677

    References, 678

    18 Copper-Catalyzed C-C Bond Formation in Natural Product Synthesis: Elegant and Efficient Solutions to a Key Bond Disconnection 683
    Morgan Donnard and Nicolas Blanchard

    18.1 Introduction, 683

    18.2 Natural Biaryls by Copper-Catalyzed Cross Coupling, 684

    18.3 Copper-Catalyzed 1,3-Enyne Formation, 691

    18.4 Copper-Mediated Synthesis of Dienes, Trienes, and Extended Polyenes, 694

    18.5 Copper-Catalyzed Synthesis of 1,N-Polyynes Natural Products, 711

    18.6 Conclusions and Future Prospects, 718

    References, 719

    19 Process Chemistry and Copper Catalysis 725
    Klaus Kunz and Norbert Lui

    19.1 Introduction and Scope, 725

    19.2 Copper versus Palladium, 727

    19.3 Applications, 727

    19.4 Conclusion, 739

    References, 740

    20 Reusable Catalysts for Copper-Mediated Cross-Coupling Reactions under Heterogeneous Conditions 745
    Zhiyong Wang, Changfeng Wan, and Ye Wang

    20.1 Introduction, 745

    20.2 Copper Nanoparticle-Catalyzed Cross-Coupling Reactions, 746

    20.3 Supported Copper-Catalyzed Cross-Coupling Reaction, 766

    20.4 Conclusion, 780

    References, 780

    INDEX 785