Modern Arylation Methods

ARYLATION REACTIONS: A HISTORICAL PERSPECTIVE Structure and Bonding of Benzene Syntheses of Substituted (Hetero)Arenes, and the Contents of this Book METAL-CATALYZED COUPLING REACTIONS WITH ARYL CHLORIDES, TOSYLATES AND FLUORIDES Introduction Coupling Reactions of Aryl Chlorides Coupling Reactions Aryl Fluorides Coupling Reactions of Aryl Tosylates PALLADIUM-CATALYZED ARYLATIONS OF AMINES AND ALPHA-C-H ACIDIC COMPOUNDS Introduction Palladium-Catalyzed Arylations of Amines Palladium-Catalyzed Arylations of Alpha-C-H Acidic Compounds COPPER-CATALYZED ARYLATIONS OF AMINES AND ALCOHOLS WITH BORON-BASED ARYLATING REAGENTS Introduction Discovery and Development of a New O-H Bond Arylation Reaction: From Stoichiometric to Catalytic in Copper Mechanistic Considerations Miscellaneous Applications Development of a New N-H Bond Arylation Reaction Development of a New N-H Bond Arylation Reaction: Catalytic in Copper METAL-CATALYZED ARYLATIONS OF NONACTIVATED ALKYL (PSEUDO)HALIDES VIA CROSS-COUPLING REACTIONS Introduction Palladium-Catalyzed Arylations of Alkyl (Pseudo)Halides Nickel-Catalyzed Arylations of Alkyl (Pseudo)Halides Iron-Catalyzed Arylations of Alkyl (Pseudo)Halides Copper- and Cobalt-Catalyzed Arylations of Alkyl (Pseudo)Halides ARYLATION REACTIONS OF ALKYNES: THE SONOGASHIRA REACTION Introduction Palladium-Catalyzed Reactions: Ligands and Reaction Protocols Alternative Metal Catalysts Mechanism of the Sonogashira Reaction PALLADIUM-CATALYZED ARYLATION REACTIONS OF ALKENES (MIZOROKI-HECK REACTION AND RELATED PROCESSES) Introduction Mizoroki-Heck Arylations Reductive Mizoroki-Heck-Type Arylations Oxidative Mizoroki-Heck-Type Arylations MODERN ARYLATIONS OF CARBONYL COMPOUNDS Introduction Enantioselective Arylation of Aldehydes Enantioselective Arylation of Ketones Enantioselective Arylation of Imines Conjugate Asymmetric Arylation Tandem Processes Enantioselective Friedel-Crafts Arylation METAL-CATALYZED DIRECT ARYLATIONS (EXCLUDING PALLADIUM) Introduction Rhodium-Catalyzed Direct Arylations Ruthenium-Catalyzed Direct Arylations Iridium-, Copper- and Iron-Catalyzed Direct Arylations PALLADIUM-CATALYZED DIRECT ARYLATION REACTIONS Introduction Intermolecular Arylation of Functionalized Arenes Intramolecular Reaction of Haloaryl-Linked Arenes Intermolecular Arylation Reactions of Heteroaromatic Compounds MECHANISTIC ASPECTS OF TRANSITION METAL-CATALYZED DIRECT ARYLATION REACTIONS Introduction Palladium-Catalyzed Intramolecular Direct Arylation Intermolecular Metal-Catalyzed Direct Arylation of Arenes Metal-Catalyzed Heteroaryl-Aryl and Heteroaryl-Heteroaryl Bond Formation Direct Arylation via Metallacycles Cross-Dehydrogenative Couplings ARYLATION REACTIONS INVOLVING THE FORMATION OF ARYNES Introduction Generation of Arynes Electrophilic Coupling of Arynes Pericyclic Reactions of Arynes Transition Metal-Catalyzed Reactions Arynes RADICAL-BASED ARYLATION METHODS Introduction SRN1-Type Radical Arylations Homolytic Aromatic Substitutions Arylations Using Aryl Radicals PHOTOCHEMICAL ARYLATION REACTIONS Introduction Photochemical Formation of Aryl-C Bonds Photochemical Formation of Aryl-N Bonds