Copper-mediated Cross-coupling Reactions

by Evano, Gwilherm; Blanchard, Nicolas

• ISBN13: 9781118060452
• ISBN10: 1118060458
• Edition: 1st
• Format: Hardcover
• Copyright: 2013-11-11
• Publisher: Wiley

Summary

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.

Author Biography

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.

Table of Contents

Introduction Copper catalysis from an historical perspective: a legacy from the past
Gwilherm Evano and Nicolas Blanchard

PART 1 FORMATION OF C-HETEROATOM BONDS

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

Chapter 2: Ullmann condensation today: arylation of alcohols and thiols with aryl halides
Anis Tlili and Marc Taillefer

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

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

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

Chapter 6: Aromatic/Vinylic Finkelstein Reaction
Alicia Casitas and Xavi Ribas

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

PART 2 FORMATION OF C-C BONDS

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

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

Chapter 10: Copper-Mediated Aryl–aryl Bond Formation Leading to Biaryls: A Century After Ullmann Breakthrough
Yoshihiko Yamamoto

Chapter 11: Copper-Catalyzed Alkynylation, Alkenylation and Allylation Reaction of Aryl Derivatives
Ren-Jie Song and Jin-Heng Li

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

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

Chapter 14: Emerging Areas in Copper-Mediated Trifluoromethylations: Catalytic and Oxidative Cross-Coupling Processes
Kévin Jouvin, Céline Guissart and Gwilherm Evano

PART 3 APPLICATIONS OF COPPER CATALYZED CROSS COUPLING REACTIONS: HETEROCYCLES, NATURAL PRODUCTS, PROCESS AND SUSTAINABLE CHEMISTRY

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

Chapter 16: Copper-Mediated C-N Bond Forming Reactions: New Opportunities in Natural Product Synthesis
Jihoon Lee and James S Panek

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

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

Chapter 19: Process Chemistry and Copper Catalysis
Klaus Kunz and Norbert Lui

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