10027cam a2200937 i 4500 ocn843026114 OCoLC 20171106120747.0 m o d cr ||||||||||| 130510s2013 nju ob 001 0 eng 2013019308 9781118690680 (pdf) 1118690680 (pdf) 9781118690475 (epub) 1118690478 (epub) 9781118690505 ( mobi) 1118690508 ( mobi) 9781118060452 (hardback) 9781118690659 1118690656 1118060458 9781118060452 9781299939660 129993966X EB00064124 Recorded Books AU@ 000051026292 CHBIS 010131724 CHDSB 006179225 CHVBK 303678445 CHVBK 314705945 NZ1 15341804 NLGGC 369366468 DEBSZ 431513325 DEBBG BV041908978 DEBBG BV043395847 (OCoLC)843026114 (OCoLC)864918046 (OCoLC)876848244 DLC eng rda DLC YDX N$T IDEBK DG1 EBLCP YDXCP OCLCF CDX COO CHVBK OTZ RECBK DEBSZ DEBBG pcc MAIN QD505 SCI 013030 bisacsh 546/.652595 23 SCI013050 bisacsh Copper-mediated cross-coupling reactions / edited by Gwilherm Evano, Laboratoire de chimie organique, Service de chimie et physicochimie organiques, Université libre de Bruxelles, Brussels, Belgium, Nicolas Blanchard, Université de Strasbourg, École européenne de chimie, polymères et Matériaux, Laboratoire de chimie moléculaire associé au CNRS, Strasbourg, France. [electronic resource] Hoboken, New Jersey : Wiley, [2013] 1 online resource. text rdacontent computer rdamedia online resource rdacarrier Machine generated contents note: 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 Kevin 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 Kevin Jouvin, Celine 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 . Includes bibliographical references and index. Title page; Copyright page; Foreword; Preface: Copper Catalysis from a Historical Perspective: A Legacy from the Past; The Historical and Remarkable First Discoveries by Fritz Ullmann and Irma Goldberg; Further Historical Developments: The Cyanation of Aryl Halides by Rosenmund and von Braun and the Arylation of Diketones and Malonates by Hurtley; From the Historical Discoveries to the Development of Modern Copper-Mediated Cross-Coupling Reactions; Modern Copper-Mediated Cross-Coupling Reactions and Their Impact in Organic Chemistry; Contributors; Part I: Formation of C-Heteroatom Bonds 1: Modern Ullmann-Goldberg Chemistry: Arylation of N-Nucleophiles with Aryl Halides1.1 Introduction; 1.2 Arylation of Amines; 1.3 Arylation of Amides, Imides, and Carbamates; 1.4 Arylation of Conjugated N-Heterocycles; 1.5 Synthesis of Anilines by Coupling with Ammonia or Synthetic Equivalents; 1.6 Conclusion and Future Prospects; 2: Ullmann Condensation Today: Arylation of Alcohols and Thiols with Aryl Halides; 2.1 Introduction; 2.2 Formation of C-O Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides 2.3 Formation of C-S Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides2.4 Conclusion; 3: Copper-Catalyzed Formation of C-P Bonds with Aryl Halides; 3.1 Introduction; 3.2 Arylation of Phosphines; 3.3 Arylation of Phosphine Oxides and Phosphites; 3.4 Conclusion; 4: Alternative and Emerging Reagents for the Arylation of Heteronucleophiles; 4.1 Introduction; 4.2 Chan-Lam-Evans Coupling: Copper(II)-Promoted Oxidative Aryl Transfer from Arylboron Derivatives; 4.3 Copper-Promoted Aryl Transfer from Metallated Aryl Derivatives (Nonboron) 4.4 Copper-Catalyzed Arylation Reactions Involving Masked S- and N-Nucleophiles4.5 Copper-Catalyzed Direct Heterofunctionalization of Aromatic C-H Bonds; 4.6 Conclusion and Future Prospects; 5: Beyond Ullmann-Goldberg Chemistry: Vinylation, Alkynylation, and Allenylation of Heteronucleophiles; 5.1 Introduction; 5.2 Copper-Mediated Alkenylation of Heteronucleophiles: Among the Best Routes to Heteroatom-Substituted Alkenes; 5.3 Alkynylation of Heteronucleophiles: The Emergence of General Methods for the Synthesis of Heteroatom-Substituted Alkynes 5.4 Allenylation of Heteronucleophiles: New Tools for the Synthesis of Allenamides5.5 Conclusion and Future Prospects; 6: Aromatic/Vinylic Finkelstein Reaction; 6.1 Introduction; 6.2 Copper-Mediated Halogen Exchange Reactions in Aryl Halides; 6.3 Most Recent Developments and Overview; 7: Insights into the Mechanism of Modern Ullmann-Goldberg Coupling Reactions; 7.1 General View and Key Mechanistic Aspects; 7.2 Oxidation State of Copper Catalysts; 7.3 Identity of the Active Copper(I) Complex; 7.4 Activation Mode of Aryl Halides by Copper Complexes "Providing insight into the use of copper in cross-coupling reactions as a cost-efficient alternative to palladium, Copper-Mediated Cross Coupling Reactions provides a complete up-to-date collection of the available catalytic systems and processes. This essential reference covers a broad scope of copper-mediated reactions, their variations, key advances, improvements, and an array of applications that have revolutionized copper catalysis for any industry involving organic synthesis. The text discusses recently developed methods for conducting copper-mediated reactions with supported catalysts, which allow for recyclable and reusable systems"-- Provided by publisher. "This book is divided into three parts: Formation of C-Heteroatom Bonds, Formation of C-C Bonds, and Applications of Copper Catalyzed Cross Coupling Reactions: Heterocycles, Natural Products, Process and Sustainable Chemistry"-- Provided by publisher. Description based on print version record and CIP data provided by publisher. Copper catalysts. Copper Reactivity. Chemical bonds. Organic compounds Synthesis. SCIENCE / Chemistry / Physical & Theoretical. bisacsh Chemical bonds. fast (OCoLC)fst00852856 Copper catalysts. fast (OCoLC)fst00878447 Copper Reactivity. fast (OCoLC)fst00878394 Organic compounds Synthesis. fast (OCoLC)fst01047668 Katalysator. (DE-588)4029919-3 gnd Kupfer. (DE-588)4033734-0 gnd Kreuzkupplungsreaktion. (DE-588)1033635499 gnd Organische Synthese. (DE-588)4075695-6 gnd Electronic books. Electronic books. Evano, Gwilherm, editor of compilation. Blanchard, Nicolas, editor of compilation. Print version: Copper-mediated cross-coupling reactions Hoboken, New Jersey : Wiley, [2013] 9781118060452 (DLC) 2013011111 http://onlinelibrary.wiley.com/book/10.1002/9781118690659 Wiley Online Library ddc BK 206723 206723