Freshly Printed - allow 7 days lead
Couldn't load pickup availability
Copper-Mediated Cross-Coupling Reactions
Gwilherm Evano (Author), Nicolas Blanchard (Author)
9781118060452, Wiley
Hardback, published 27 December 2013
848 pages
24.1 x 16.5 x 4.8 cm, 1.32 kg
“The book is a key resource for copper chemistry and a must-have, for experts and students alike.” (Angewandte Chemie, 30 May 2014)
Providing comprehensive insight into the use of copper in cross-coupling reactions, Copper-Mediated Cross-Coupling Reactions provides a complete up-to-date collection of the available reactions and catalytic systems for the formation of carbon-heteroatom and carbon-carbon bonds. This essential reference covers a broad scope of copper-mediated reactions, their variations, key advances, improvements, and an array of academic and industrial applications that have revolutionized the field of organic synthesis. The text also discusses the mechanism of these transformations, the use of copper as cost-efficient alternative to palladium, as well as recently developed methods for conducting copper-mediated reactions with supported catalysts.
Foreword xvii Preface: Copper Catalysis From a Historical Perspective: A Legacy From the Past xix Contributors xxxiii Part I Formation of C–heteroatom Bonds 1 1 Modern Ullmann–Goldberg Chemistry: Arylation of N-Nucleophiles with Aryl Halides 3 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 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 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 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 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 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 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 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 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 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 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 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 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 Trifluoromethylations of Aryl Derivatives: Catalytic and Oxidative Cross-Coupling Processes 515 14.1 Introduction 515 14.2 Copper-Catalyzed Trifluoromethylation of Aryl Halides: A Long-Lasting Quest Finally Reached 517 14.3 Copper-Mediated Oxidative Trifluoromethylation 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 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 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 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 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 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 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
Stephen L. Buchwald
Gwilherm Evano and Nicolas Blanchard
Yongwen Jiang and Dawei Ma
Anis Tlili and Marc Taillefer
Carole Alayrac and Annie-Claude Gaumont
Luc Neuville
Kévin Jouvin and Gwilherm Evano
Alicia Casitas and Xavi Ribas
Alicia Casitas and Xavi Ribas
Irina P. Beletskaya and Alexey Yu. Fedorov
Thomas Schareina and Matthias Beller
Yoshihiko Yamamoto
Ren-Jie Song and Jin-Heng li
Ruimao Hua
Hao Li Songbai Liu and Lanny S. Liebeskind
Kévin Jouvin Céline Guissart Cédric Theunissen and Gwilherm Evano
Daoshan Yang and Hua Fu
Jihoon Lee and James S. Panek
Doron Pappo
Morgan Donnard and Nicolas Blanchard
Klaus Kunz and Norbert Lui
Zhiyong Wang Changfeng Wan and Ye Wang
Subject Areas: Chemistry [PN]
