Modern Arylation Methods

  • ID: 686776
  • Book
  • 561 Pages
  • John Wiley and Sons Ltd
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Today, arylation methods belong to the most important reaction types in organic synthesis. The editor 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 various hot topics, such as palladium– or copper–catalyzed arylations of amines, alcohols and alpha–C–H–acidic compounds, catalytic direct Arylation reactions, as well as arylations of alkenes and alkynes, among others.

This compact source of high quality information is indispensable to synthetic chemists in academia, as well as those working in the pharmaceutical and chemical industry.

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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

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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).
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