Modern arylation methods [[electronic resource] /] / edited by Lutz Ackermann

• Record Nr.: UNINA9910830710703321
• Pubbl/distr/stampa: Weinheim, : Wiley-VCH, c2009
• ISBN: 1-282-11850-1; 9786612118500; 3-527-62733-2
• Descrizione fisica: 1 online resource (563 p.)
• Altri autori (Persone): AckermannLutz
• Disciplina: 541.39
• Soggetti: Arylation; Organic compounds - Synthesis
• Lingua di pubblicazione: Inglese
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Note generali: Description based upon print version of record.
• Nota di bibliografia: Includes bibliographical references and index.
• Nota di contenuto: Modern Arylation Methods; Contents; Preface; List of Contributors; 1 Arylation Reactions: A Historical Perspective; 1.1 Structure and Bonding of Benzene; 1.2 Syntheses of Substituted (Hetero)Arenes, and the Contents of this Book; Abbreviations; References; 2 Metal-Catalyzed Coupling Reactions with Aryl Chlorides, Tosylates and Fluorides; 2.1 Introduction; 2.2 Coupling Reactions of Aryl Chlorides; 2.2.1 Nickel-Catalyzed Cross-Couplings of Aryl Chlorides; 2.2.2 Palladium-Catalyzed Cross-Coupling Reactions; 2.2.2.1 Suzuki Reaction; 2.2.2.2 Stille Reaction; 2.2.2.3 Hiyama Coupling; 2.2.2.4 Negishi Coupling2.2.2.5 Kumada Coupling; 2.3 Coupling Reactions of Aryl Fluorides; 2.4 Coupling Reactions of Aryl Tosylates; 2.5 Conclusions; Abbreviations; References; 3 Palladium-Catalyzed Arylations of Amines and α-C-H Acidic Compounds; 3.1 Introduction; 3.2 Palladium-Catalyzed Arylations of Amines; 3.2.1 Historical Development; 3.2.2 Catalytic Systems; 3.2.2.1 Palladium Sources; 3.2.2.2 Ligands; 3.2.2.3 Bases; 3.2.2.4 Solvents; 3.2.3 Aryl Halides; 3.2.4 Arylsulfonic Acid Esters; 3.2.5 Heteroaromatic Electrophiles; 3.2.6 Amines as Nucleophiles; 3.2.7 Amine Derivatives as Nucleophiles3.2.8 Applications; 3.2.9 Mechanistic Aspects; 3.2.10 Chirality; 3.3 Palladium-Catalyzed Arylations of α-C-H Acidic Compounds; 3.3.1 Historical Development; ; 3.3.2 Catalytic Systems; 3.3.3 α-Arylations of Esters; 3.3.4 α-Arylations of Malonates and α-Cyano Esters; 3.3.5 α-Arylations of Ketones; 3.3.6 α-Arylations of Amides; 3.3.7 α-Arylations of Nitriles; 3.4 Summary and Conclusions; Abbreviations; References; 4 Copper-Catalyzed Arylations of Amines and Alcohols with Boron-Based Arylating Reagents; 4.1 Introduction; 4.2 Discovery and Development of a New O-H Bond Arylation Reaction: From Stoichiometric to Catalytic in Copper4.3 Mechanistic Considerations; 4.4 Miscellaneous Applications; 4.4.1 Additional Applications with ArB(OH)(2); 4.4.2 Alternatives to ArB(OH)(2); 4.4.3 Alternatives to Phenols; 4.5 Development of a New N-H Bond Arylation Reaction; 4.5.1 Stoichiometric in Copper; 4.5.2 Alternatives to Boronic Acids; 4.6 Development of a New N-H Bond Arylation Reaction: Catalytic in Copper; 4.6.1 Proposed Mechanism; 4.6.2 Additional Important Non-N-H Arylation Examples; 4.7 Summary and Conclusions; AbbreviationsReferences; 5 Metal-Catalyzed Arylations of Nonactivated Alkyl (Pseudo)Halides via Cross-Coupling Reactions; 5.1 Introduction; 5.2 Palladium-Catalyzed Arylations of Alkyl (Pseudo)Halides; 5.3 Nickel-Catalyzed Arylations of Alkyl (Pseudo)Halides; 5.4 Iron-Catalyzed Arylations of Alkyl (Pseudo)Halides; 5.5 Copper- and Cobalt-Catalyzed Arylations of Alkyl (Pseudo)Halides; Abbreviations; References; 6 Arylation Reactions of Alkynes: The Sonogashira Reaction; 6.1 Introduction; 6.2 Palladium-Catalyzed Reactions: Ligands and Reaction Protocols; 6.2.1 Phosphine-Based Ligands; 6.2.1.1 Copper-Free Catalytic Systems
• Sommario/riassunto: Today, arylation methods are belonging to the most important reaction types in organic synthesis. Lutz Ackermann, a young and ambitious professor has gathered a number of top international authors to present the first comprehensive book on the topic. Starting from a historical review, the book covers hot topics like Palladium-catalyzed arylation of N-H and alpha-C-H-acidic Bonds, Copper-catalyzed arylation of N-H and O-H Bonds, direct arylation reactions, carbanion aromatic synthesis, arylation reactions of alkenes, alkynes and much more. This compact source of high quality information