{"product_id":"arene-chemistry-9781118752012","title":"Arene Chemistry","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003eOrganized to enable students and synthetic chemists to understand and expand on aromatic reactions covered in foundation courses, the book offers a thorough and accessible mechanistic explanation of aromatic reactions involving arene compounds.\u003cbr\u003e\u003cbr\u003e Surveys methods used for preparing arene compounds and their transformations\u003cbr\u003e Connects reactivity and methodology with mechanism\u003cbr\u003e Helps readers apply aromatic reactions in a practical context by designing syntheses\u003cbr\u003e Provides essential information about techniques used to determine reaction mechanisms\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTrade Review\u003c\/b\u003e\u003cbr\u003e\"The broad covering of topics, made possible by the collaboration of world-renowned experts in different\u003cbr\u003efields of organic chemistry and by a good balance in depth of coverage, positions [this book] as a deskbook that would be extremely useful for students of advanced courses of organic chemistry, instructors and professors, as well as experienced chemists in both academy and industry, and to those interested in arene chemistry and its application.\" -- Chemistry International\u003cbr\u003e\u003cbr\u003e\" ... Jacques Mortier has brought together contributions from leading practitioners in universities and research institutes from around the world to create a concise but comprehensive text on aromatic chemistry. ... They have effectively condensed the essential material, and made an ideal source of information ...\" -- Applied Organometallic Chemistry\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003eLIST OF CONTRIBUTORS xxi\u003c\/p\u003e \u003cp\u003ePREFACE xxv\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART I ELECTROPHILIC AROMATIC SUBSTITUTION 1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 Electrophilic Aromatic Substitution: Mechanism 3\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eDouglas A. Klumpp\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e1.1 Introduction, 3\u003c\/p\u003e \u003cp\u003e1.2 General Aspects, 4\u003c\/p\u003e \u003cp\u003e1.3 Electrophiles, 4\u003c\/p\u003e \u003cp\u003e1.4 Arene Nucleophiles, 12\u003c\/p\u003e \u003cp\u003e1.5 π‐Complex Intermediates, 17\u003c\/p\u003e \u003cp\u003e1.6 σ‐Complex or Wheland Intermediates, 22\u003c\/p\u003e \u003cp\u003e1.7 Summary and Outlook, 27\u003c\/p\u003e \u003cp\u003eAbbreviations, 27\u003c\/p\u003e \u003cp\u003eReferences, 28\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Friedel–Crafts Alkylation of Arenes in Total Synthesis 33\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eGonzalo Blay, Marc Montesinos‐Magraner, and José R. Pedro\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e2.1 Introduction, 33\u003c\/p\u003e \u003cp\u003e2.2 Total Synthesis Involving Intermolecular FC Alkylations, 34\u003c\/p\u003e \u003cp\u003e2.3 Total Synthesis Involving Intramolecular FC Alkylations, 37\u003c\/p\u003e \u003cp\u003e2.4 Total Synthesis Through Tandem and Cascade Processes Involving FC Reactions, 46\u003c\/p\u003e \u003cp\u003e2.5 Total Synthesis Involving ipso‐FC Reactions, 54\u003c\/p\u003e \u003cp\u003e2.6 Summary and Outlook, 56\u003c\/p\u003e \u003cp\u003e2.7 Acknowledgment, 56\u003c\/p\u003e \u003cp\u003eAbbreviations, 56\u003c\/p\u003e \u003cp\u003eReferences, 57\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Catalytic Friedel–Crafts Acylation Reactions 59\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eGiovanni Sartori, Raimondo Maggi, and Veronica Santacroce\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction and Historical Background, 59\u003c\/p\u003e \u003cp\u003e3.2 Catalytic Homogeneous Acylations, 60\u003c\/p\u003e \u003cp\u003e3.3 Catalytic Heterogeneous Acylations, 64\u003c\/p\u003e \u003cp\u003e3.4 Direct Phenol Acylation, 73\u003c\/p\u003e \u003cp\u003e3.5 Summary and Outlook, 77\u003c\/p\u003e \u003cp\u003eAbbreviations, 78\u003c\/p\u003e \u003cp\u003eReferences, 78\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 The Use of Quantum Chemistry for Mechanistic Analyses of SEAr Reactions 83\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTore Brinck and Magnus Liljenberg\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction, 83\u003c\/p\u003e \u003cp\u003e4.2 The SEAr Mechanism: Quantum Chemical Characterization in Gas Phase and Solution, 87\u003c\/p\u003e \u003cp\u003e4.3 Prediction of Relative Reactivity and Regioselectivity Based on Quantum Chemical Descriptors, 97\u003c\/p\u003e \u003cp\u003e4.4 Quantum Chemical Reactivity Prediction Based on Modeling of Transition States and Intermediates, 100\u003c\/p\u003e \u003cp\u003e4.5 Summary and Conclusions, 102\u003c\/p\u003e \u003cp\u003eAbbreviations, 103\u003c\/p\u003e \u003cp\u003eReferences, 103\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Catalytic Enantioselective Electrophilic Aromatic Substitutions 107\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMarco Bandini\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction and Historical Background, 107\u003c\/p\u003e \u003cp\u003e5.2 Metal‐Catalyzed AFCA of Aromatic Hydrocarbons, 109\u003c\/p\u003e \u003cp\u003e5.3 Organocatalyzed AFCA of Aromatic Hydrocarbons, 116\u003c\/p\u003e \u003cp\u003e5.4 Merging Asymmetric Metal and Organocatalysis in Friedel–Crafts Alkylations, 125\u003c\/p\u003e \u003cp\u003e5.5 Summary and Outlook, 126\u003c\/p\u003e \u003cp\u003eAbbreviations, 127\u003c\/p\u003e \u003cp\u003eReferences, 127\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART II NUCLEOPHILIC AROMATIC SUBSTITUTION 131\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Nucleophilic Aromatic Substitution: An Update Overview 133\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMichael R. Crampton\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction, 133\u003c\/p\u003e \u003cp\u003e6.2 The SNAr Mechanism, 135\u003c\/p\u003e \u003cp\u003e6.3 Meisenheimer Adducts, 150\u003c\/p\u003e \u003cp\u003e6.4 The SN1 Mechanism, 159\u003c\/p\u003e \u003cp\u003e6.4.1 Heterolytic and Homolytic Pathways, 159\u003c\/p\u003e \u003cp\u003e6.5 Synthetic Applications, 160\u003c\/p\u003e \u003cp\u003eAbbreviations, 167\u003c\/p\u003e \u003cp\u003eReferences, 167\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Theoretical and Experimental Methods for the Analysis of Reaction Mechanisms in SNAr Processes: Fugality, Philicity, and Solvent Effects 175\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eRenato Contreras, Paola R. Campodónico, and Rodrigo Ormazábal‐Toledo\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction, 175\u003c\/p\u003e \u003cp\u003e7.2 Conceptual DFT: Global, Regional, and Nonlocal Reactivity Indices, 176\u003c\/p\u003e \u003cp\u003e7.3 Practical Applications of Conceptual DFT Descriptors, 179\u003c\/p\u003e \u003cp\u003e7.4 SNAr Reaction Mechanism, 183\u003c\/p\u003e \u003cp\u003e7.5 Integrated Experimental and Theoretical Models, 187\u003c\/p\u003e \u003cp\u003e7.6 Solvent Effects in Conventional Solvents and Ionic Liquids, 188\u003c\/p\u003e \u003cp\u003e7.7 Summary and Outlook, 189\u003c\/p\u003e \u003cp\u003eAbbreviations, 190\u003c\/p\u003e \u003cp\u003eReferences, 190\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Asymmetric Nucleophilic Aromatic Substitution 195\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eAnne‐Sophie Castanet, Anne Boussonnière, and Jacques Mortier\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction, 195\u003c\/p\u003e \u003cp\u003e8.2 Auxiliary‐ and Substrate‐Controlled Asymmetric Nucleophilic Aromatic Substitution, 198\u003c\/p\u003e \u003cp\u003e8.3 Chiral Catalyzed Asymmetric Nucleophilic Aromatic Substitution, 210\u003c\/p\u003e \u003cp\u003e8.4 Absolute Asymmetric Nucleophilic Aromatic Substitution, 213\u003c\/p\u003e \u003cp\u003e8.5 Summary and Outlook, 214\u003c\/p\u003e \u003cp\u003eAbbreviations, 214\u003c\/p\u003e \u003cp\u003eReferences, 215\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Homolytic Aromatic Substitution 219\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eRoberto A. Rossi, María E. Budén, and Javier F. Guastavino\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction: Scope and Limitations, 219\u003c\/p\u003e \u003cp\u003e9.2 Radicals Generated by Homolytic Cleavage Processes: Thermolysis and Photolysis, 223\u003c\/p\u003e \u003cp\u003e9.3 Reactions Mediated by Tin and Silicon Hydrides, 225\u003c\/p\u003e \u003cp\u003e9.4 Radicals Generated by ET: Redox Reactions, 229\u003c\/p\u003e \u003cp\u003e9.5 Summary and Outlook, 237\u003c\/p\u003e \u003cp\u003eAbbreviations, 238\u003c\/p\u003e \u003cp\u003eReferences, 238\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Radical‐Nucleophilic Aromatic Substitution 243\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eRoberto A. Rossi, Javier F. Guastavino, and María E. Budén\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction: Scope and Limitations—Background, 243\u003c\/p\u003e \u003cp\u003e10.2 Mechanistic Considerations, 245\u003c\/p\u003e \u003cp\u003e10.3 Intermolecular SRN1 Reactions, 248\u003c\/p\u003e \u003cp\u003e10.4 Intramolecular SRN1 Reactions, 258\u003c\/p\u003e \u003cp\u003e10.5 Miscellaneous Ring Closure Reactions, 262\u003c\/p\u003e \u003cp\u003e10.6 Summary and Outlook, 264\u003c\/p\u003e \u003cp\u003eAbbreviations, 265\u003c\/p\u003e \u003cp\u003eReferences, 265\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Nucleophilic Substitution of Hydrogen in Electron‐Deficient Arenes 269\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMieczysław Mąkosza\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction, 269\u003c\/p\u003e \u003cp\u003e11.2 Oxidative Nucleophilic Substitution of Hydrogen, 270\u003c\/p\u003e \u003cp\u003e11.3 Conversion of the σH‐Adducts of Nucleophiles to Nitroarenes into Substituted Nitrosoarenes, 276\u003c\/p\u003e \u003cp\u003e11.4 Vicarious Nucleophilic Substitution of Hydrogen, 278\u003c\/p\u003e \u003cp\u003e11.5 Other Ways of Conversion of the σH‐Adducts, 291\u003c\/p\u003e \u003cp\u003e11.6 Concluding Remarks, 293\u003c\/p\u003e \u003cp\u003eAbbreviations, 295\u003c\/p\u003e \u003cp\u003eReferences, 295\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART III ARYNE CHEMISTRY 299\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12 The Chemistry of Arynes: An Overview 301\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eRoberto Sanz and Anisley Suárez\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction, 301\u003c\/p\u003e \u003cp\u003e12.2 Structure and Representative Reactions of Arynes, 301\u003c\/p\u003e \u003cp\u003e12.3 Aryne Generation, 303\u003c\/p\u003e \u003cp\u003e12.4 Pericyclic Reactions, 306\u003c\/p\u003e \u003cp\u003e12.5 Nucleophilic Addition Reactions to Arynes, 314\u003c\/p\u003e \u003cp\u003e12.6 Transition Metal–Catalyzed Reactions of Arynes, 327\u003c\/p\u003e \u003cp\u003e12.7 Conclusion, 332\u003c\/p\u003e \u003cp\u003eAbbreviations, 332\u003c\/p\u003e \u003cp\u003eReferences, 333\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART IV REDUCTION, OXIDATION, AND DEAROMATIZATION REACTIONS 337\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13 Reduction\/Hydrogenation of Aromatic Rings 339\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eFrancisco Foubelo and Miguel Yus\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e13.1 Introduction, 339\u003c\/p\u003e \u003cp\u003e13.2 The Birch Reaction, 339\u003c\/p\u003e \u003cp\u003e13.3 Metal‐Catalyzed Hydrogenations, 345\u003c\/p\u003e \u003cp\u003e13.4 Electrochemical Reductions, 357\u003c\/p\u003e \u003cp\u003e13.5 Other Methodologies, 359\u003c\/p\u003e \u003cp\u003e13.6 Summary and Outlook, 361\u003c\/p\u003e \u003cp\u003eAbbreviations, 361\u003c\/p\u003e \u003cp\u003eReferences, 362\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14 Selective Oxidation of Aromatic Rings 365\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eOxana A. Kholdeeva\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e14.1 Introduction, 365\u003c\/p\u003e \u003cp\u003e14.2 Mechanistic Principles, 367\u003c\/p\u003e \u003cp\u003e14.3 Stoichiometric Oxidations, 374\u003c\/p\u003e \u003cp\u003e14.4 Catalytic Oxidations, 375\u003c\/p\u003e \u003cp\u003e14.5 Photochemical Oxidations, 386\u003c\/p\u003e \u003cp\u003e14.6 Electrochemical Oxidations, 387\u003c\/p\u003e \u003cp\u003e14.7 Enzymatic Hydroxylation, 389\u003c\/p\u003e \u003cp\u003e14.8 Summary and Outlook, 390\u003c\/p\u003e \u003cp\u003eAcknowledgments, 391\u003c\/p\u003e \u003cp\u003eAbbreviations, 391\u003c\/p\u003e \u003cp\u003eReferences, 392\u003c\/p\u003e \u003cp\u003e\u003cb\u003e15 Dearomatization Reactions: An Overview 399\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eF. Christopher Pigge\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e15.1 Introduction, 399\u003c\/p\u003e \u003cp\u003e15.2 Alkylative Dearomatization, 400\u003c\/p\u003e \u003cp\u003e15.3 Photochemical and Thermal Dearomatization, 405\u003c\/p\u003e \u003cp\u003e15.4 Oxidative Dearomatization, 408\u003c\/p\u003e \u003cp\u003e15.5 Transition Metal‐Assisted Dearomatization, 413\u003c\/p\u003e \u003cp\u003e15.6 Enzymatic Dearomatization, 418\u003c\/p\u003e \u003cp\u003e15.7 Conclusions and Future Directions, 419\u003c\/p\u003e \u003cp\u003eAbbreviations, 419\u003c\/p\u003e \u003cp\u003eReferences, 420\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART V AROMATIC REARRANGEMENTS 425\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e16 Aromatic Compounds via Pericyclic Reactions 427\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eSethuraman Sankararaman\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e16.1 Introduction, 427\u003c\/p\u003e \u003cp\u003e16.2 Electrocyclic Ring Closure Reaction, 428\u003c\/p\u003e \u003cp\u003e16.3 Introduction to Cycloaddition Reactions, 433\u003c\/p\u003e \u003cp\u003e16.4 Conclusions, 448\u003c\/p\u003e \u003cp\u003eAbbreviations, 448\u003c\/p\u003e \u003cp\u003eReferences, 448\u003c\/p\u003e \u003cp\u003e\u003cb\u003e17 Ring‐Closing Metathesis: Synthetic Routes to Carbocyclic Aromatic Compounds using Ring‐Closing Alkene and Enyne Metathesis 451\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eCharles B. de Koning and Willem A. L. van Otterlo\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e17.1 Introduction, 451\u003c\/p\u003e \u003cp\u003e17.2 Alkene RCM for the Synthesis of Aromatic Compounds, 454\u003c\/p\u003e \u003cp\u003e17.3 Enyne Metathesis Followed by the Diels–Alder Reaction for the Synthesis of Benzene Rings in Complex Aromatic Compounds, 464\u003c\/p\u003e \u003cp\u003e17.4 Cyclotrimerization for the Synthesis of Aromatic Compounds by Metathetic Processes, 470\u003c\/p\u003e \u003cp\u003e17.5 Strategies for the Synthesis of Aromatic Carbocycles Fused to Heterocycles by the RCM Reaction, 472\u003c\/p\u003e \u003cp\u003e17.6 Future Challenges, 481\u003c\/p\u003e \u003cp\u003e17.7 Conclusions, 481\u003c\/p\u003e \u003cp\u003eAbbreviations, 482\u003c\/p\u003e \u003cp\u003eReferences, 482\u003c\/p\u003e \u003cp\u003e\u003cb\u003e18 Aromatic Rearrangements in which the Migrating Group Migrates to the Aromatic Nucleus: An Overview 485\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eTimothy J. Snape\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e18.1 Introduction, 485\u003c\/p\u003e \u003cp\u003e18.2 Mechanisms by Classification, 486\u003c\/p\u003e \u003cp\u003e18.3 Summary and Outlook, 508\u003c\/p\u003e \u003cp\u003eAbbreviations, 508\u003c\/p\u003e \u003cp\u003eReferences, 508\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART VI TRANSITION METAL‐MEDIATED COUPLING 511\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e19 Transition Metal‐Catalyzed Carbon–Carbon Cross‐Coupling 513\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eAnny Jutand and Guillaume Lefèvre\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e19.1 Introduction, 513\u003c\/p\u003e \u003cp\u003e19.2 The Mizoroki–Heck Reaction, 513\u003c\/p\u003e \u003cp\u003e19.3 Cross‐Coupling of Aryl Halides with Anionic C‐Nucleophiles, 523\u003c\/p\u003e \u003cp\u003e19.4 The Sonogashira Reaction, 530\u003c\/p\u003e \u003cp\u003e19.5 The Stille Reaction, 532\u003c\/p\u003e \u003cp\u003e19.6 The Suzuki–Miyaura Reaction, 534\u003c\/p\u003e \u003cp\u003e19.7 The Hiyama Reaction, 539\u003c\/p\u003e \u003cp\u003e19.8 Summary and Outlook, 541\u003c\/p\u003e \u003cp\u003eAbbreviations, 541\u003c\/p\u003e \u003cp\u003eReferences, 541\u003c\/p\u003e \u003cp\u003e\u003cb\u003e20 Transition Metal‐Mediated Carbon–Heteroatom Cross‐Coupling (C─N, C─O, C─S, C─Se, C─Te, C─P, C─As, C─Sb, and C─B Bond Forming Reactions): An Overview 547\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMasanam Kannan, Mani Sengoden, and Tharmalingam Punniyamurthy\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e20.1 Introduction, 547\u003c\/p\u003e \u003cp\u003e20.2 C—N Cross‐Coupling, 550\u003c\/p\u003e \u003cp\u003e20.3 C—O Cross‐Coupling, 561\u003c\/p\u003e \u003cp\u003e20.4 C—S Cross‐Coupling, 569\u003c\/p\u003e \u003cp\u003e20.5 C—Se Cross‐Coupling, 571\u003c\/p\u003e \u003cp\u003e20.6 C—Te Cross‐Coupling, 571\u003c\/p\u003e \u003cp\u003e20.7 C—P Cross‐Coupling, 572\u003c\/p\u003e \u003cp\u003e20.8 C—As and C—Sb Cross‐Coupling, 578\u003c\/p\u003e \u003cp\u003e20.9 C—B Cross‐Coupling, 578\u003c\/p\u003e \u003cp\u003e20.10 Summary and Outlook, 579\u003c\/p\u003e \u003cp\u003eAbbreviations, 579\u003c\/p\u003e \u003cp\u003eReferences, 579\u003c\/p\u003e \u003cp\u003e\u003cb\u003e21 Transition Metal‐Mediated Aromatic Ring Construction 587\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eKen Tanaka\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e21.1 Introduction, 587\u003c\/p\u003e \u003cp\u003e21.2 [2+2+2] Cycloaddition, 587\u003c\/p\u003e \u003cp\u003e21.3 [3+2+1] Cycloaddition, 601\u003c\/p\u003e \u003cp\u003e21.4 [4+2] Cycloaddition, 602\u003c\/p\u003e \u003cp\u003e21.5 Intramolecular Cycloaromatization, 608\u003c\/p\u003e \u003cp\u003e21.6 Summary and Outlook, 612\u003c\/p\u003e \u003cp\u003eReferences, 612\u003c\/p\u003e \u003cp\u003e\u003cb\u003e22 Ar–C Bond Formation by Aromatic Carbon–Carbon ipso‐Substitution Reaction 615\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMaurizio Fagnoni and Sergio M. Bonesi\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e22.1 Introduction, 615\u003c\/p\u003e \u003cp\u003e22.2 Formation of Ar–C(sp3) Bonds, 616\u003c\/p\u003e \u003cp\u003e22.3 Formation of Ar–C(sp2) Bonds, 620\u003c\/p\u003e \u003cp\u003e22.4 Formation of Ar–C(sp) Bonds, 638\u003c\/p\u003e \u003cp\u003e22.5 Summary and Outlook, 639\u003c\/p\u003e \u003cp\u003eAbbreviations, 639\u003c\/p\u003e \u003cp\u003eReferences, 640\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART VII C─H FUNCTIONALIZATION 645\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e23 Chelate‐Assisted Arene C–H Bond Functionalization 647\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMarion H. Emmert and Christopher J. Legacy\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e23.1 Introduction, 647\u003c\/p\u003e \u003cp\u003e23.2 Carbon–Carbon (C–C) Bond Formations, 654\u003c\/p\u003e \u003cp\u003e23.3 Carbon–Heteroatom (C–X) Bond Formations, 660\u003c\/p\u003e \u003cp\u003e23.4 Stereoselective C–H Functionalizations, 668\u003c\/p\u003e \u003cp\u003eAbbreviations, 669\u003c\/p\u003e \u003cp\u003eReferences, 669\u003c\/p\u003e \u003cp\u003e\u003cb\u003e24 Reactivity and Selectivity in Transition Metal‐Catalyzed, Nondirected Arene Functionalizations 675\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eDipannita Kalyani and Elodie E. Marlier\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e24.1 Introduction, 675\u003c\/p\u003e \u003cp\u003e24.2 Arylation, 676\u003c\/p\u003e \u003cp\u003e24.3 Alkenylation, 693\u003c\/p\u003e \u003cp\u003e24.4 Alkylation, 699\u003c\/p\u003e \u003cp\u003e24.5 Carboxylation, 701\u003c\/p\u003e \u003cp\u003e24.6 Oxygenation, 701\u003c\/p\u003e \u003cp\u003e24.7 Thiolation, 704\u003c\/p\u003e \u003cp\u003e24.8 Amination, 706\u003c\/p\u003e \u003cp\u003e24.9 Miscellaneous, 708\u003c\/p\u003e \u003cp\u003e24.10 Summary and Outlook, 710\u003c\/p\u003e \u003cp\u003eAbbreviations, 710\u003c\/p\u003e \u003cp\u003eReferences, 710\u003c\/p\u003e \u003cp\u003e\u003cb\u003e25 Functionalization of Arenes via C─H Bond Activation Catalysed by Transition Metal Complexes: Synergy between Experiment and Theory 715\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eAmalia Isabel Poblador‐Bahamonde\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e25.1 Introduction, 715\u003c\/p\u003e \u003cp\u003e25.2 Mechanisms of C─H Bond Activation, 716\u003c\/p\u003e \u003cp\u003e25.3 Development of Stoichiometric C─H Bond Activation, 718\u003c\/p\u003e \u003cp\u003e25.4 Catalytic C─H Activation and Functionalization, 730\u003c\/p\u003e \u003cp\u003e25.5 Summary, 738\u003c\/p\u003e \u003cp\u003eAbbreviations, 738\u003c\/p\u003e \u003cp\u003eReferences, 738\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART VIII DIRECTED METALATION REACTIONS 741\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e26 Directed Metalation of Arenes with Organolithiums, Lithium Amides, and Superbases 743\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eFrédéric R. Leroux and Jacques Mortier\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e26.1 Introduction, 743\u003c\/p\u003e \u003cp\u003e26.2 Preparation and Reactivity of Organolithium Compounds, 744\u003c\/p\u003e \u003cp\u003e26.3 Directed ortho-Metalation (DoM), 748\u003c\/p\u003e \u003cp\u003e26.4 Directed remote Metalation (DreM), 757\u003c\/p\u003e \u003cp\u003e26.5 Peri Lithiation of Substituted Naphthalenes, 759\u003c\/p\u003e \u003cp\u003e26.6 Lithiation of Metal Arene Complexes, 760\u003c\/p\u003e \u003cp\u003e26.7 Lateral Lithiation, 761\u003c\/p\u003e \u003cp\u003e26.8 Analytical Methods, 762\u003c\/p\u003e \u003cp\u003e26.9 Synthetic Applications, 765\u003c\/p\u003e \u003cp\u003e26.10 Conclusion, 770\u003c\/p\u003e \u003cp\u003eAbbreviations, 771\u003c\/p\u003e \u003cp\u003eReferences, 771\u003c\/p\u003e \u003cp\u003e\u003cb\u003e27 Deprotonative Metalation Using Alkali Metal–Nonalkali Metal Combinations 777\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eFloris Chevallier, Florence Mongin, Ryo Takita, and Masanobu Uchiyama\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e27.1 Introduction, 777\u003c\/p\u003e \u003cp\u003e27.2 Preparation of the Bimetallic Combinations and their Structural Features, 778\u003c\/p\u003e \u003cp\u003e27.3 Behavior of Alkali Metal–Nonalkali Metal Combinations, 779\u003c\/p\u003e \u003cp\u003e27.4 Mechanistic Studies on the Deprotometalation Using Alkali Metal–Nonalkali Metal Combinations, 780\u003c\/p\u003e \u003cp\u003e27.5 Scope and Applications of the Deprotometalation, 790\u003c\/p\u003e \u003cp\u003e27.6 Conclusion and Perspectives, 807\u003c\/p\u003e \u003cp\u003eAcknowledgments, 807\u003c\/p\u003e \u003cp\u003eAbbreviations, 807\u003c\/p\u003e \u003cp\u003eReferences, 807\u003c\/p\u003e \u003cp\u003e\u003cb\u003e28 The Halogen\/Metal Interconversion and Related Processes (M = Li, Mg) 813\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eArmen Panossian and Frédéric R. Leroux\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e28.1 Introduction, 813\u003c\/p\u003e \u003cp\u003e28.2 Generalities, 814\u003c\/p\u003e \u003cp\u003e \u003c\/p\u003e \u003cp\u003e28.3.1 Reactivity, 815\u003c\/p\u003e \u003cp\u003e28.2.1 Monometallic Organolithium Reagents, 814\u003cbr\u003e\u003cbr\u003e28.3 Mechanism of the Halogen\/Metal Interconversion, 815\u003c\/p\u003e \u003cp\u003e28.4 Halogen Migration on Aromatic Compounds, 817\u003c\/p\u003e \u003cp\u003e28.5 Selective Synthesis via Halogen\/Metal Interconversion, 818\u003c\/p\u003e \u003cp\u003e28.6 The Sulfoxide\/Metal and Phosphorus\/Metal Interconversions, 822\u003c\/p\u003e \u003cp\u003e28.7 Aryl─Aryl Coupling Through Halogen\/Metal Interconversion, 827\u003c\/p\u003e \u003cp\u003e28.8 Summary and Outlook, 830\u003c\/p\u003e \u003cp\u003eAbbreviations, 830\u003c\/p\u003e \u003cp\u003eReferences, 830\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART IX PHOTOCHEMICAL REACTIONS 835\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e29 Aromatic Photochemical Reactions 837\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eNorbert Hoffmann and Emmanuel Riguet\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e29.1 Introduction, 837\u003c\/p\u003e \u003cp\u003e29.2 Aromatic Compounds as Chromophores, 838\u003c\/p\u003e \u003cp\u003e29.3 Photosensitized and Photocatalyzed Reactions, 849\u003c\/p\u003e \u003cp\u003e29.4 Conclusion, 864\u003c\/p\u003e \u003cp\u003eAbbreviation, 865\u003c\/p\u003e \u003cp\u003eReferences, 865\u003c\/p\u003e \u003cp\u003e\u003cb\u003e30 Photochemical Bergman Cyclization and Related Reactions 869\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eRana K. Mohamed, Kemal Kaya, and Igor V. Alabugin\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e30.1 Introduction: The Diversity of Cycloaromatization Reactions, 869\u003c\/p\u003e \u003cp\u003e30.2 Electronic Factors in Photo‐BC, 870\u003c\/p\u003e \u003cp\u003e30.3 Scope and Limitations of the Photo‐BC, 876\u003c\/p\u003e \u003cp\u003e30.4 Enediyne Photocyclizations: Tool for Cancer Therapy, 883\u003c\/p\u003e \u003cp\u003e30.5 Conclusion, 883\u003c\/p\u003e \u003cp\u003eAbbreviations, 885\u003c\/p\u003e \u003cp\u003eReferences, 885\u003c\/p\u003e \u003cp\u003e\u003cb\u003e31 Photo‐Fries Reaction and Related Processes 889\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eFrancisco Galindo, M. Consuelo Jiménez, and Miguel Angel Miranda\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e31.1 Introduction, 889\u003c\/p\u003e \u003cp\u003e31.2 Mechanistic Aspects, 889\u003c\/p\u003e \u003cp\u003e31.3 Scope of the Reaction, 894\u003c\/p\u003e \u003cp\u003e31.4 (Micro)Heterogeneous Systems as Reaction Media, 897\u003c\/p\u003e \u003cp\u003e31.5 Applications in Organic Synthesis, 900\u003c\/p\u003e \u003cp\u003e31.6 Biological and Industrial Applications, 902\u003c\/p\u003e \u003cp\u003e31.7 Summary and Outlook, 905\u003c\/p\u003e \u003cp\u003eAbbreviations, 906\u003c\/p\u003e \u003cp\u003eReferences, 906\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePART X BIOTRANSFORMATIONS 913\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e32 Biotransformations of Arenes: An Overview 915\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eSimon E. Lewis\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e32.1 Introduction, 915\u003c\/p\u003e \u003cp\u003e32.2 Dearomatizing Arene Dihydroxylation, 915\u003c\/p\u003e \u003cp\u003e32.3 Dearomatizing Arene Epoxidation, 918\u003c\/p\u003e \u003cp\u003e32.4 Arene Alkylation (Biocatalytic Friedel–Crafts), 919\u003c\/p\u003e \u003cp\u003e32.5 Arene Deacylation (Biocatalytic Retro Friedel–Crafts), 922\u003c\/p\u003e \u003cp\u003e32.6 Arene Carboxylation (Biocatalytic Kolbe–Schmitt), 923\u003c\/p\u003e \u003cp\u003e32.7 Arene Halogenation (Halogenases), 925\u003c\/p\u003e \u003cp\u003e32.8 Arene Oxidation with Laccases, 925\u003c\/p\u003e \u003cp\u003e32.9 Tetrahydroisoquinoline Synthesis (Biocatalytic Pictet–Spengler), 929\u003c\/p\u003e \u003cp\u003e32.10 Arene Hydroxylation, 930\u003c\/p\u003e \u003cp\u003e32.11 Arene Nitration, 932\u003c\/p\u003e \u003cp\u003e32.12 Summary and Outlook, 933\u003c\/p\u003e \u003cp\u003eAbbreviations, 934\u003c\/p\u003e \u003cp\u003eReferences, 934\u003c\/p\u003e \u003cp\u003eINDEX 939\u003c\/p\u003e","brand":"Wiley","offers":[{"title":"Default Title","offer_id":53515636769111,"sku":"9781118752012","price":145.76,"currency_code":"GBP","in_stock":true}],"url":"https:\/\/bookcurl.com\/products\/arene-chemistry-9781118752012","provider":"Book Curl","version":"1.0","type":"link"}