Free Download Arene Chemistry by Jacques Mortier

Reaction Mechanisms and Methods for Aromatic Compounds

Authors:

Jacques Mortier

Table of Contents

PART I ELECTROPHILIC AROMATIC SUBSTITUTION 1

1 Electrophilic Aromatic Substitution: Mechanism 3

2 Friedel–Crafts Alkylation of Arenes in Total Synthesis

3 Catalytic Friedel–Crafts Acylation Reactions 59

4 The Use of Quantum Chemistry for Mechanistic Analyses of SEAr Reactions

5 Catalytic Enantioselective Electrophilic Aromatic Substitutions 107

PART II NUCLEOPHILIC AROMATIC SUBSTITUTION 131

6 Nucleophilic Aromatic Substitution: An Update Overview

7 Theoretical and Experimental Methods for the Analysis of Reaction Mechanisms in SNAr Processes: Fugality, Philicity, and Solvent Effects 175

8 Asymmetric Nucleophilic Aromatic Substitution 195

9 Homolytic Aromatic Substitution 219

10 Radical‐Nucleophilic Aromatic Substitution 243

11 Nucleophilic Substitution of Hydrogen in Electron‐Deficient Arenes 269

PART III ARYNE CHEMISTRY 299

12 The Chemistry of Arynes: An Overview

PART IV REDUCTION, OXIDATION, AND DEAROMATIZATION REACTIONS 337

13 Reduction/Hydrogenation of Aromatic Rings 339

14 Selective Oxidation of Aromatic Rings

15 Dearomatization Reactions: An Overview 399

PART V AROMATIC REARRANGEMENTS 425

16 Aromatic Compounds via Pericyclic Reactions

17 Ring‐Closing Metathesis: Synthetic Routes to Carbocyclic Aromatic Compounds using Ring‐Closing Alkene and Enyne Metathesis 451

18 Aromatic Rearrangements in which the Migrating Group Migrates to the Aromatic Nucleus: An Overview

Arene Chemistry by Jacques Mortier

PART VI TRANSITION METAL‐MEDIATED COUPLING 511

19 Transition Metal‐Catalyzed Carbon–Carbon Cross‐Coupling 513

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): An Overview 547

21 Transition Metal‐Mediated Aromatic Ring Construction 587

22 Ar–C Bond Formation by Aromatic Carbon–Carbon ipso‐Substitution Reaction 615

PART VII C─H FUNCTIONALIZATION 645

23 Chelate‐Assisted Arene C–H Bond Functionalization 647

24 Reactivity and Selectivity in Transition Metal‐Catalyzed, Nondirected Arene Functionalizations 675

25 Functionalization of Arenes via C─H Bond Activation Catalysed by Transition Metal Complexes: Synergy between Experiment and Theory 715

PART VIII DIRECTED METALATION REACTIONS 741

26 Directed Metalation of Arenes with Organolithiums, Lithium Amides, and Superbases 743

27 Deprotonative Metalation Using Alkali Metal–Nonalkali Metal Combinations 777

28 The Halogen/Metal Interconversion and Related Processes (M = Li, Mg)

PART IX PHOTOCHEMICAL REACTIONS 835

29 Aromatic Photochemical Reactions 837

30 Photochemical Bergman Cyclization and Related Reactions 869

31 Photo‐Fries Reaction and Related Processes 889

PART X BIOTRANSFORMATIONS 913

32 Biotransformations of Arenes: An Overview

INDEX

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