Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds

Copyright © 2016 John Wiley & Sons, Inc.

Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds

Editor(s): Jacques Mortier

Published Online: 27 NOV 2015 09:42PM EST

Print ISBN: 9781118752012

Online ISBN: 9781118754887

DOI: 10.1002/9781118754887

About this Book

Organized to enable students and synthetic chemists to understand and expand on aromatic reactions covered in foundation courses, the book offers a thorough and accessible mechanistic explanation of aromatic reactions involving arene compounds.

•    Surveys methods used for preparing arene compounds and their transformations
•    Connects reactivity and methodology with mechanism
•    Helps readers apply aromatic reactions in a practical context by designing syntheses
•    Provides essential information about techniques used to determine reaction mechanisms

Table of contents

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      Front Matter (pages i–xxvii)

  2. Part I: Electrophilic Aromatic Substitution

    1. Chapter 1

      Electrophilic Aromatic Substitution (pages 1–31)

      Douglas A. Klumpp

    1. Chapter 2

      Friedel–Crafts Alkylation of Arenes in Total Synthesis (pages 33–58)

      Gonzalo Blay, Marc Montesinos-Magraner and José R. Pedro

    1. Chapter 3

      Catalytic Friedel–Crafts Acylation Reactions (pages 59–82)

      Giovanni Sartori, Raimondo Maggi and Veronica Santacroce

    1. Chapter 4

      The Use of Quantum Chemistry for Mechanistic Analyses of SEAr Reactions (pages 83–105)

      Tore Brinck and Magnus Liljenberg

    1. Chapter 5

      Catalytic Enantioselective Electrophilic Aromatic Substitutions (pages 107–129)

      Marco Bandini

  7. Part II: Nucleophilic Aromatic Substitution

    1. Chapter 6

      Nucleophilic Aromatic Substitution (pages 131–173)

      Michael R. Crampton

    1. Chapter 7

      Theoretical and Experimental Methods for the Analysis of Reaction Mechanisms in SNAr Processes (pages 175–193)

      Renato Contreras, Paola R. Campodónico and Rodrigo Ormazábal-Toledo

    1. Chapter 8

      Asymmetric Nucleophilic Aromatic Substitution (pages 195–217)

      Anne-Sophie Castanet, Anne Boussonnière and Jacques Mortier

    1. Chapter 9

      Homolytic Aromatic Substitution (pages 219–242)

      Roberto A. Rossi, María E. Budén and Javier F. Guastavino

    1. Chapter 10

      Radical-Nucleophilic Aromatic Substitution (pages 243–268)

      Roberto A. Rossi, Javier F. Guastavino and María E. Budén

    1. Chapter 11

      Nucleophilic Substitution of Hydrogen in Electron-Deficient Arenes (pages 269–298)

      Mieczysław Mąkosza

  13. Part III: Aryne Chemistry

    1. Chapter 12

      The Chemistry of Arynes (pages 299–336)

      Roberto Sanz and Anisley Suárez

  14. Part IV: Reduction, Oxidation, and Dearomatization Reactions

    1. Chapter 13

      Reduction/Hydrogenation of Aromatic Rings (pages 337–364)

      Francisco Foubelo and Miguel Yus

    1. Chapter 14

      Selective Oxidation of Aromatic Rings (pages 365–398)

      Oxana A. Kholdeeva

    1. Chapter 15

      Dearomatization Reactions (pages 399–423)

      F. Christopher Pigge

  17. Part V: Aromatic Rearrangements

    1. Chapter 16

      Aromatic Compounds Via Pericyclic Reactions (pages 425–449)

      Sethuraman Sankararaman

    1. Chapter 17

      Ring-Closing Metathesis (pages 451–484)

      Charles B. de Koning and Willem A. L. van Otterlo

    1. Chapter 18

      Aromatic Rearrangements in Which the Migrating Group Migrates to the Aromatic Nucleus (pages 485–510)

      Timothy J. Snape

  20. Part VI: Transition Metal-Mediated Coupling

    1. Chapter 19

      Transition Metal-Catalyzed Carbon–Carbon Cross-Coupling (pages 511–545)

      Anny Jutand and Guillaume Lefèvre

    1. Chapter 20

      Transition Metal-Mediated Carbon–Heteroatom Cross-Coupling (C—N, C—O, C—S, C—Se, C—Te, C—P, C—As, C—Sb, and C—B Bond Forming Reactions) (pages 547–586)

      Masanam Kannan, Mani Sengoden and Tharmalingam Punniyamurthy

    1. Chapter 21

      Transition Metal-Mediated Aromatic Ring Construction (pages 587–614)

      Ken Tanaka

    1. Chapter 22

      Ar–C Bond Formation by Aromatic Carbon–Carbon Ipso-Substitution Reaction (pages 615–644)

      Maurizio Fagnoni and Sergio M. Bonesi

  24. Part VII: C—H Functionalization

    1. Chapter 23

      Chelate-Assisted Arene C–H Bond Functionalization (pages 645–673)

      Marion H. Emmert and Christopher J. Legacy

    1. Chapter 24

      Reactivity and Selectivity in Transition Metal-Catalyzed, Nondirected Arene Functionalizations (pages 675–713)

      Dipannita Kalyani and Elodie E. Marlier

    1. Chapter 25

      Functionalization of Arenes Via C—H Bond Activation Catalysed by Transition Metal Complexes (pages 715–740)

      Amalia Isabel Poblador-Bahamonde

  27. Part VIII: Directed Metalation Reactions

    1. Chapter 26

      Directed Metalation of Arenes with Organolithiums, Lithium Amides, and Superbases (pages 741–776)

      Frédéric R. Leroux and Jacques Mortier

    1. Chapter 27

      Deprotonative Metalation Using Alkali Metal–Nonalkali Metal Combinations (pages 777–812)

      Floris Chevallier, Florence Mongin, Ryo Takita and Masanobu Uchiyama

    1. Chapter 28

      The Halogen/Metal Interconversion and Related Processes (M = Li, Mg) (pages 813–833)

      Armen Panossian and Frédéric R. Leroux

  30. Part IX: Photochemical Reactions

    1. Chapter 29

      Aromatic Photochemical Reactions (pages 835–868)

      Norbert Hoffmann and Emmanuel Riguet

    1. Chapter 30

      Photochemical Bergman Cyclization and Related Reactions (pages 869–887)

      Rana K. Mohamed, Kemal Kaya and Igor V. Alabugin

    1. Chapter 31

      Photo-Fries Reaction and Related Processes (pages 889–911)

      Francisco Galindo, M. Consuelo Jiménez and Miguel Angel Miranda

  33. Part X: Biotransformations

    1. Chapter 32

      Biotransformations of Arenes (pages 913–937)

      Simon E. Lewis

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      Index (pages 939–959)

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