Modern Arylation Methods

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 is indispensable to synthetic chemists and those working in the pharmaceutical and chemical industry.

Table of Contents:
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

About the Author :
Lutz Ackermann was educated at the Christian-Albrechts-University Kiel, Germany, and obtained his Ph.D. in 2001 under the supervision of Alois Furstner, Max-Plank-Institut fur Kohlenforschung in Mulheim/Ruhr. He was a DAAD postdoctoral fellow in the laboratories of Robert G. Berman at the University of California at Berkeley, USA, and initiated his independent career - supported by the Emmy Noether-program (DFG) - in 2003 at the Ludwig-Maximilians-University in Munich. In 2007, he became a full professor at the Georg-August-University Gottingen. The unifying theme of his research program is represented by the development of novel concepts for efficient catalytic processes. Lutz Ackermann was visiting professor at the Universita degli Studi di Milano, Italy, as well as the University of Wisconsin at Madison, USA, and his recent awards include an ORCHEM-prize, an ADUC-prize, and a Dozentenstipendium (FCI).