{"product_id":"copper-mediated-cross-coupling-reactions-isbn-9781118060452","title":"Copper-Mediated Cross-Coupling Reactions","description":"\u003cp\u003eProviding comprehensive insight into the use of copper in cross-coupling reactions, \u003ci\u003eCopper-Mediated Cross-Coupling Reactions\u003c\/i\u003e 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.\u003c\/p\u003e \u003cp\u003eForeword xvii\u003cbr\u003e \u003ci\u003eStephen L. Buchwald\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003ePreface: Copper Catalysis From a Historical Perspective: A Legacy From the Past xix\u003cbr\u003e \u003ci\u003eGwilherm Evano and Nicolas Blanchard\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003eContributors xxxiii\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart I Formation of C–heteroatom Bonds 1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 Modern Ullmann–Goldberg Chemistry: Arylation of N-Nucleophiles with Aryl Halides 3\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eYongwen Jiang and Dawei Ma\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e1.1 Introduction 3\u003c\/p\u003e \u003cp\u003e1.2 Arylation of Amines 4\u003c\/p\u003e \u003cp\u003e1.3 Arylation of Amides Imides and Carbamates 15\u003c\/p\u003e \u003cp\u003e1.4 Arylation of Conjugated N-Heterocycles 24\u003c\/p\u003e \u003cp\u003e1.5 Synthesis of Anilines by Coupling with Ammonia or Synthetic Equivalents 32\u003c\/p\u003e \u003cp\u003e1.6 Conclusion and Future Prospects 37\u003c\/p\u003e \u003cp\u003eReferences 37\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Ullmann Condensation Today: Arylation of Alcohols and Thiols with Aryl Halides 41\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eAnis Tlili and Marc Taillefer\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e2.1 Introduction 41\u003c\/p\u003e \u003cp\u003e2.2 Formation of C–O Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides 42\u003c\/p\u003e \u003cp\u003e2.3 Formation of C–S Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides 67\u003c\/p\u003e \u003cp\u003e2.4 Conclusion 84\u003c\/p\u003e \u003cp\u003eReferences 86\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Copper-Catalyzed Formation of C–P Bonds with Aryl Halides 93\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eCarole Alayrac and Annie-Claude Gaumont\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction 93\u003c\/p\u003e \u003cp\u003e3.2 Arylation of Phosphines 94\u003c\/p\u003e \u003cp\u003e3.3 Arylation of Phosphine Oxides and Phosphites 98\u003c\/p\u003e \u003cp\u003e3.4 Conclusion 110\u003c\/p\u003e \u003cp\u003eReferences 110\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Alternative and Emerging Reagents for the Arylation of Heteronucleophiles 113\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eLuc Neuville\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction 113\u003c\/p\u003e \u003cp\u003e4.2 Chan–Lam–Evans Coupling: Copper(II)-Promoted Oxidative Aryl Transfer from Arylboron Derivatives 115\u003c\/p\u003e \u003cp\u003e4.3 Copper-Promoted Aryl Transfer from Metallated Aryl Derivatives (Nonboron) 141\u003c\/p\u003e \u003cp\u003e4.4 Copper-Catalyzed Arylation Reactions Involving Masked S- and N-Nucleophiles 151\u003c\/p\u003e \u003cp\u003e4.5 Copper-Catalyzed Direct Heterofunctionalization of Aromatic C–H Bonds 160\u003c\/p\u003e \u003cp\u003e4.6 Conclusion and Future Prospects 178\u003c\/p\u003e \u003cp\u003eReferences 178\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Beyond Ullmann–Goldberg Chemistry: Vinylation Alkynylation and Allenylation of Heteronucleophiles 187\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eKévin Jouvin and Gwilherm Evano\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction 187\u003c\/p\u003e \u003cp\u003e5.2 Copper-Mediated Alkenylation of Heteronucleophiles: Among the Best Routes to Heteroatom-Substituted Alkenes 189\u003c\/p\u003e \u003cp\u003e5.3 Alkynylation of Heteronucleophiles: The Emergence of General Methods for the Synthesis of Heteroatom-Substituted Alkynes 219\u003c\/p\u003e \u003cp\u003e5.4 Allenylation of Heteronucleophiles: New Tools for the Synthesis of Allenamides 232\u003c\/p\u003e \u003cp\u003e5.5 Conclusion and Future Prospects 233\u003c\/p\u003e \u003cp\u003eReferences 234\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Aromatic\/Vinylic Finkelstein Reaction 239\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eAlicia Casitas and Xavi Ribas\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction 239\u003c\/p\u003e \u003cp\u003e6.2 Copper-Mediated Halogen Exchange Reactions in Aryl Halides 241\u003c\/p\u003e \u003cp\u003e6.3 Most Recent Developments and Overview 247\u003c\/p\u003e \u003cp\u003eReferences 249\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Insights into the Mechanism of Modern Ullmann–Goldberg Coupling Reactions 253\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eAlicia Casitas and Xavi Ribas\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e7.1 General View and Key Mechanistic Aspects 253\u003c\/p\u003e \u003cp\u003e7.2 Oxidation State of Copper Catalysts 254\u003c\/p\u003e \u003cp\u003e7.3 Identity of the Active Copper(I) Complex 255\u003c\/p\u003e \u003cp\u003e7.4 Activation Mode of Aryl Halides by Copper Complexes 261\u003c\/p\u003e \u003cp\u003e7.5 Overview Conclusions and Future Prospects 275\u003c\/p\u003e \u003cp\u003eReferences 277\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart II Formation of C–c Bonds 281\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Modern Copper-Catalyzed Hurtley Reaction: Efficient C-Arylation of CH-Acid Derivatives 283\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eIrina P. Beletskaya and Alexey Yu. Fedorov\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction 283\u003c\/p\u003e \u003cp\u003e8.2 Classical Hurtley Reaction 285\u003c\/p\u003e \u003cp\u003e8.3 Ligation Effect in Copper-Catalyzed Reactions of Aryl Halides with Carbanions 286\u003c\/p\u003e \u003cp\u003e8.4 Cascade Reactions Proceeding via a Hurtley Arylation Reaction 293\u003c\/p\u003e \u003cp\u003e8.5 Mechanism of the Copper-Catalyzed C-Arylation Reactions 303\u003c\/p\u003e \u003cp\u003e8.6 Concluding Remarks 308\u003c\/p\u003e \u003cp\u003eReferences 308\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Copper-Catalyzed Cyanations of Aryl Halides and Related Compounds 313\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eThomas Schareina and Matthias Beller\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction 313\u003c\/p\u003e \u003cp\u003e9.2 Modifications and Updates of Classical Cyanation Reactions (Rosenmund–von Braun Sandmeyer) 315\u003c\/p\u003e \u003cp\u003e9.3 Copper-Catalyzed Cyanations of Aryl Halides 316\u003c\/p\u003e \u003cp\u003e9.4 Copper-Mediated Oxidative Cyanations 324\u003c\/p\u003e \u003cp\u003e9.5 Conclusion 331\u003c\/p\u003e \u003cp\u003eReferences 331\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Copper-Mediated Aryl–Aryl Bond Formation Leading to Biaryls: A Century after the Ullmann Breakthrough 335\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eYoshihiko Yamamoto\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction 335\u003c\/p\u003e \u003cp\u003e10.2 Biaryl Synthesis by Coupling of Aryl Halides and Diazonium Salts 336\u003c\/p\u003e \u003cp\u003e10.3 Biaryl Synthesis by Coupling of Aryltin Boron and Silanes 347\u003c\/p\u003e \u003cp\u003e10.4 Biaryl Synthesis by Arylation Involving Arene C–H or C–C Bond Fission 357\u003c\/p\u003e \u003cp\u003e10.5 Biaryl Synthesis by Oxidative Coupling of 2-Naphthols 376\u003c\/p\u003e \u003cp\u003e10.6 Conclusions and Outlook 387\u003c\/p\u003e \u003cp\u003eReferences 388\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Copper-Catalyzed Alkynylation Alkenylation and Allylation Reactions of Aryl Derivatives 401\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eRen-Jie Song and Jin-Heng li\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction 401\u003c\/p\u003e \u003cp\u003e11.2 Copper-Catalyzed Alkynylation of Aryl Derivatives 402\u003c\/p\u003e \u003cp\u003e11.3 Copper-Catalyzed Alkenylation of Aryl Derivatives 432\u003c\/p\u003e \u003cp\u003e11.4 Copper-Catalyzed Strategies for the Formation of Allyl–Aryl Bonds 445\u003c\/p\u003e \u003cp\u003e11.5 Conclusion and Outlook 450\u003c\/p\u003e \u003cp\u003eReferences 450\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12 Copper-Catalyzed Alkynylation and Alkenylation Reactions of Alkynyl Derivatives: New Access to Diynes and Enynes 455\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eRuimao Hua\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction 455\u003c\/p\u003e \u003cp\u003e12.2 Copper-Catalyzed Synthesis of Symmetrical and Unsymmetrical 1,3-Diynes 456\u003c\/p\u003e \u003cp\u003e12.3 Copper-Catalyzed Synthesis of 1,4-Diynes 468\u003c\/p\u003e \u003cp\u003e12.4 Synthesis of 1,3-Enynes by Direct Reaction of Vinyl Halides with Alkynes 468\u003c\/p\u003e \u003cp\u003e12.5 Synthesis of 1,3-Enynes by Stille-Type Cross-Coupling Reaction 474\u003c\/p\u003e \u003cp\u003e12.6 Synthesis of 1,3-Enynes by the Suzuki–Miyaura-Type Cross-Coupling Reaction 476\u003c\/p\u003e \u003cp\u003e12.7 Synthesis of 1,4-Enynes by Allylation Reaction of Terminal Alkynes 478\u003c\/p\u003e \u003cp\u003e12.8 Conclusion 480\u003c\/p\u003e \u003cp\u003eReferences 480\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13 Copper-Mediated Alkenylation Reaction of Alkenyl Derivatives: A Straightforward Elaboration of 1,3-Dienes 485\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eHao Li Songbai Liu and Lanny S. Liebeskind\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e13.1 Introduction 485\u003c\/p\u003e \u003cp\u003e13.2 Symmetrical 1,3-Dienes by Homocoupling Reaction of Vinyl Derivatives 486\u003c\/p\u003e \u003cp\u003e13.3 Unsymmetrical 1,3-Dienes by Cross-Coupling Reactions 496\u003c\/p\u003e \u003cp\u003e13.4 Conclusions 510\u003c\/p\u003e \u003cp\u003eReferences 511\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14 Emerging Areas in Copper-Mediated Trifluoromethylations of Aryl Derivatives: Catalytic and Oxidative Cross-Coupling Processes 515\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eKévin Jouvin Céline Guissart Cédric Theunissen and Gwilherm Evano\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e14.1 Introduction 515\u003c\/p\u003e \u003cp\u003e14.2 Copper-Catalyzed Trifluoromethylation of Aryl Halides: A Long-Lasting Quest Finally Reached 517\u003c\/p\u003e \u003cp\u003e14.3 Copper-Mediated Oxidative Trifluoromethylation Reactions 523\u003c\/p\u003e \u003cp\u003e14.4 Conclusion and Future Prospects 528\u003c\/p\u003e \u003cp\u003eReferences 528\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart III Applications of Copper-catalyzed Cross-coupling Reactions: Heterocycles Natural Products Process and Sustainable Chemistry 531\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e15 Copper-Mediated Cyclization Reactions: New Entries to Heterocycles 533\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eDaoshan Yang and Hua Fu\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e15.1 Introduction 533\u003c\/p\u003e \u003cp\u003e15.2 Cyclization by C–N Bond Formation 534\u003c\/p\u003e \u003cp\u003e15.3 Cyclization by C–O Bond Formation 560\u003c\/p\u003e \u003cp\u003e15.4 Cyclization by C–C Bond Formation 567\u003c\/p\u003e \u003cp\u003e15.5 Copper-Catalyzed Double Cross-Coupling Reactions for the Assembly of Heterocycles 576\u003c\/p\u003e \u003cp\u003e15.6 Conclusion and Future Prospects 583\u003c\/p\u003e \u003cp\u003eReferences 584\u003c\/p\u003e \u003cp\u003e\u003cb\u003e16 Application of Copper-Mediated C–N Bond Formation in Complex Molecules Synthesis 589\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eJihoon Lee and James S. Panek\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e16.1 Introduction 589\u003c\/p\u003e \u003cp\u003e16.2 Aryl Amination in Complex Molecule Synthesis 590\u003c\/p\u003e \u003cp\u003e16.3 Aryl Amidation in Complex Molecule Synthesis 595\u003c\/p\u003e \u003cp\u003e16.4 Arylation of N-Heterocycles in Complex Molecule Synthesis 601\u003c\/p\u003e \u003cp\u003e16.5 Vinyl Amidation in Complex Molecule Synthesis 606\u003c\/p\u003e \u003cp\u003e16.6 Alkyne Amidation in Complex Molecule Synthesis 620\u003c\/p\u003e \u003cp\u003e16.7 Intramolecular C–N Bond Formation in Natural Product Synthesis 622\u003c\/p\u003e \u003cp\u003e16.8 Summary and Outlook 637\u003c\/p\u003e \u003cp\u003eReferences 638\u003c\/p\u003e \u003cp\u003e\u003cb\u003e17 Natural Products and C–O\/C–S Bond-Forming Reactions: Copper Showed the Way 643\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eDoron Pappo\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e17.1 Introduction 643\u003c\/p\u003e \u003cp\u003e17.2 Total Synthesis of Naturally Occurring Diaryl Ethers by Arylation of Phenols 644\u003c\/p\u003e \u003cp\u003e17.3 Intramolecular Diaryl Ether Bond-Forming Reactions 659\u003c\/p\u003e \u003cp\u003e17.4 Arylation of Alcohols 666\u003c\/p\u003e \u003cp\u003e17.5 Vinylation of Alcohols 673\u003c\/p\u003e \u003cp\u003e17.6 Copper-Mediated C–S Bond Formation in Natural Product Synthesis 675\u003c\/p\u003e \u003cp\u003e17.7 Conclusion and Future Prospects 677\u003c\/p\u003e \u003cp\u003eReferences 678\u003c\/p\u003e \u003cp\u003e\u003cb\u003e18 Copper-Catalyzed C–C Bond Formation in Natural Product Synthesis: Elegant and Efficient Solutions to a Key Bond Disconnection 683\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eMorgan Donnard and Nicolas Blanchard\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e18.1 Introduction 683\u003c\/p\u003e \u003cp\u003e18.2 Natural Biaryls by Copper-Catalyzed Cross Coupling 684\u003c\/p\u003e \u003cp\u003e18.3 Copper-Catalyzed 1,3-Enyne Formation 691\u003c\/p\u003e \u003cp\u003e18.4 Copper-Mediated Synthesis of Dienes Trienes and Extended Polyenes 694\u003c\/p\u003e \u003cp\u003e18.5 Copper-Catalyzed Synthesis of 1,N-Polyynes Natural Products 711\u003c\/p\u003e \u003cp\u003e18.6 Conclusions and Future Prospects 718\u003c\/p\u003e \u003cp\u003eReferences 719\u003c\/p\u003e \u003cp\u003e\u003cb\u003e19 Process Chemistry and Copper Catalysis 725\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eKlaus Kunz and Norbert Lui\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e19.1 Introduction and Scope 725\u003c\/p\u003e \u003cp\u003e19.2 Copper versus Palladium 727\u003c\/p\u003e \u003cp\u003e19.3 Applications 727\u003c\/p\u003e \u003cp\u003e19.4 Conclusion 739\u003c\/p\u003e \u003cp\u003eReferences 740\u003c\/p\u003e \u003cp\u003e\u003cb\u003e20 Reusable Catalysts for Copper-Mediated Cross-Coupling Reactions under Heterogeneous Conditions 745\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eZhiyong Wang Changfeng Wan and Ye Wang\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e20.1 Introduction 745\u003c\/p\u003e \u003cp\u003e20.2 Copper Nanoparticle-Catalyzed Cross-Coupling Reactions 746\u003c\/p\u003e \u003cp\u003e20.3 Supported Copper-Catalyzed Cross-Coupling Reaction 766\u003c\/p\u003e \u003cp\u003e20.4 Conclusion 780\u003c\/p\u003e \u003cp\u003eReferences 780\u003c\/p\u003e \u003cp\u003eIndex 785 \u003c\/p\u003e  \u003cp\u003e“The book is a key resource for copper chemistry and a must-have, for experts and students alike.”  (\u003ci\u003eAngewandte Chemie\u003c\/i\u003e, 30 May 2014)\u003c\/p\u003e \u003cp\u003e \u003c\/p\u003e  \u003cp\u003e\u003cb\u003eGWILHERM EVANO\u003c\/b\u003e 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.\u003c\/p\u003e \u003cp\u003e\u003cb\u003eNICOLAS BLANCHARD\u003c\/b\u003e 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.\u003c\/p\u003e  \u003cp\u003e\u003cb\u003eComplete, up-to-date collection of available catalytic systems and processes\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eReviewing 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.\u003c\/p\u003e \u003cp\u003eStarting with the Ullmann and Goldberg cross-coupling reactions, \u003ci\u003eCopper-Mediated Cross-Coupling Reactions\u003c\/i\u003e 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:\u003c\/p\u003e \u003cul\u003e \u003cli\u003eAdvances that have revolutionized pharmaceutical, polymer, and materials synthesis\u003c\/li\u003e \u003cli\u003eCopper-mediated procedures that have been successfully employed to assemble complex targets\u003c\/li\u003e \u003cli\u003eAdvantages and limitations of using different catalytic systems and cross-coupling partners\u003c\/li\u003e \u003cli\u003eCopper-catalyzed cross-coupling reactions in natural product\/bioactive molecule synthesis\u003c\/li\u003e \u003cli\u003eNew methods for conducting copper-mediated reactions with supported catalysts that enable recyclable and reusable systems\u003c\/li\u003e \u003c\/ul\u003e \u003cp\u003eThe 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.\u003c\/p\u003e \u003cp\u003eBy setting forth the latest procedures, methods, and applications, \u003ci\u003eCopper-Mediated Cross-Coupling Reactions\u003c\/i\u003e enables investigators to efficiently synthesize pharmaceuticals, polymers, and materials as well as create a broad array of natural products and molecular structures.\u003c\/p\u003e","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47988991754469,"sku":"NP9781118060452","price":231.95,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9781118060452.jpg?v=1761782343","url":"https:\/\/k12savings.com\/products\/copper-mediated-cross-coupling-reactions-isbn-9781118060452","provider":"K12savings","version":"1.0","type":"link"}