Copper–Mediated Cross–Coupling Reactions

Complete, up-to-date collection of available catalytic systems and processes Reviewing the latest advances in copper-catalyzed reactions for the formation of carbon-heteroatom and carbon-carbon bonds, this book enables readers to understand what is currently known and possible in the field, as well as where additional research is still needed. The book's comprehensive coverage offers insights into the underlying mechanisms, preparation procedures, and state-of-the-science strategies for copper-catalyzed reactions. Moreover, readers will find a complete collection of available reactions, catalytic systems and processes, as well as current and pending patents. Starting with the Ullmann and Goldberg cross-coupling reactions, Copper-Mediated Cross-Coupling Reactions describes core applications and key advances in the field. The first two sections are dedicated to the formation of C-heteroatom bonds and C-C bonds. The third section explores applications of copper-catalyzed cross-coupling reactions, including industrial uses, and the development of environmentally friendly reactions. Among the highlights of coverage, readers will discover: Advances that have revolutionized pharmaceutical, polymer, and materials synthesis Copper-mediated procedures that have been successfully employed to assemble complex targets Advantages and limitations of using different catalytic systems and cross-coupling partners Copper-catalyzed cross-coupling reactions in natural product/bioactive molecule synthesis New methods for conducting copper-mediated reactions with supported catalysts that enable recyclable and reusable systems The book features contributions from an international team of experts and pioneers in the field. Chapters are based on a thorough review and analysis of the literature as well as the authors' firsthand experience. By setting forth the latest procedures, methods, and applications, Copper-Mediated Cross-Coupling Reactions enables investigators to efficiently synthesize pharmaceuticals, polymers, and materials as well as create a broad array of natural products and molecular structures.

Preface: Copper Catalysis from a 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 the Ullmann Breakthrough Yoshihiko Yamamoto Chapter 11: Copper–Catalyzed Alkynylation, Alkenylation and Allylation Reactions 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 of Aryl Derivatives: Catalytic and Oxidative Cross–Coupling Processes Kévin Jouvin, Céline Guissart, Cédric Theunissen 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: Application of Copper–Mediated C–N Bond Formation in Complex Molecules 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 Cross–Coupling Reactions under Heterogeneous Conditions Zhiyong Wang, Changfeng Wan and Ye Wang

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.