Modern Arylation Methods
1st Edition
Published on 22. April 2009
XVIII, 543 pages
978-3-527-62733-2 (ISBN)
Description
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.
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.
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Modern Arylation Methods
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Modern Arylation Methods
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Person
Lutz Ackermann was educated at the Christian-Albrechts-University Kiel, Germany, and obtained his Ph.D. in 2001 under the supervision of Alois Fürstner, Max-Plank-Institut für Kohlenforschung in Mülheim/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 Göttingen. 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 Università 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).
Content
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
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
