Gwilherm Evano, Nicolas Blanchard

Copper-Mediated Cross-Coupling Reactions

• Gebundenes Buch

Produktbeschreibung

Providing comprehensive insight into the use of copper incross-coupling reactions, Copper-Mediated Cross-CouplingReactions provides a complete up-to-date collection of theavailable reactions and catalytic systems for the formation ofcarbon-heteroatom and carbon-carbon bonds. This essential referencecovers a broad scope of copper-mediated reactions, theirvariations, key advances, improvements, and an array of academicand industrial applications that have revolutionized the field oforganic synthesis. The text also discusses the mechanism ofthese transformations, the use of copper as cost-efficientalternative to palladium, as well as recently developed methods forconducting copper-mediated reactions with supported catalysts.

Produktdetails

• Verlag: Wiley & Sons
• 1. Auflage
• Seitenzahl: 840
• Erscheinungstermin: 11. November 2013
• Englisch
• Abmessung: 241mm x 166mm x 50mm
• Gewicht: 1321g
• ISBN-13: 9781118060452
• ISBN-10: 1118060458
• Artikelnr.: 38082379

Autorenporträt

GWILHERM EVANO is a Professor at the Université Libre de Bruxelles and the Co-Director of the Laboratory of Organic Chemistry. Prof. Evano's research focuses on the development of copper-mediated transformations, chemistry of ynamides and other hetero-substituted alkynes, and total synthesis of natural products. NICOLAS BLANCHARD is Research Director at the French National Center for Scientific Research at the University of Strasbourg. Dr. Blanchard's research interests focus on the synthesis of biologically relevant compounds using metal-mediated transformations.

Inhaltsangabe

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