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Title Metal free C-H functionalization of aromatics : nucleophilic displacement of hydrogen / edited by Valery Charushin, Oleg Chupakhin
Published Berlin : Springer, 2014

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Description 1 online resource
Series Topics in heterocyclic chemistry ; 37
Topics in heterocyclic chemistry ; 37.
Contents Intro; Preface; Reference; Contents; Metal-Free C-H Functionalization of Aromatic Compounds Through the Action of Nucleophilic Reagents; 1 Introduction; 2 Historical Aspects of the SNH Reactions; 3 The Key Features and Scope of the SNH Reactions; 3.1 Oxidative Version of the SNH Reactions; 3.2 Eliminative Version of the SNH Reactions; 4 Aromatic and Heteroaromatic Substrates; 4.1 Unactivated Arenes; 4.2 Arenes and Hetarenes Activated by the Nitro Group; 4.3 Arene-Metal Complexes; 4.4 Metallabenzenes; 4.5 Azines, Quaternary Azinium Salts, and Azine N-Oxides; 4.6 Azoles; 4.7 Macroheterocycles
5 Nucleophilic Reagents5.1 Nitrogen-Centered Nucleophiles; 5.1.1 Ammonia, Primary, and Secondary Aliphatic Amines; 5.1.2 Aromatic Amines as N-Nucleophiles; 5.2 Oxygen-Centered Nucleophiles; 5.2.1 Water; 5.2.2 Alcohols; 5.3 Carbon-Centered Nucleophiles; 5.3.1 Carbanions Generated from C-H-Active Compounds; 5.3.2 Grignard Reagents; 5.3.3 Carbanions Generated from Ferrocenes and Cymantrenes; 5.3.4 Carbanions Generated from Carboranes; 5.3.5 Carbanions Generated from Nitronyl Nitroxide Radicals; 5.3.6 Aromatic Amines as C-Nucleophiles; 5.3.7 Phenols as C-Nucleophiles; 5.4 P-Nucleophiles
5.5 S-Nucleophiles6 Intramolecular SNH Reactions; 7 Tandem SNH-SNH, SNH-SNX, and SNH-Metal-Catalyzed Cross-Coupling Reactions; 8 Electrochemical Version of the SNH Reactions; 9 Mechanistic Aspects of the SNH Reactions; 9.1 Electron Transfer Complexes Between Reactants; 9.2 Formation of Intermediate sigmaH-Adducts; 9.2.1 Spectroscopic Evidence for the Formation of sigmaH-Adducts; 9.2.2 X-Ray Data; 9.3 Oxidation of Intermediate sigmaH-Adducts; 10 Concluding Remarks; References; Nucleophilic Substitution of Hydrogen in Arenes and Heteroarenes; 1 Introduction
2 Vicarious Nucleophilic Substitution of Hydrogen2.1 Mechanism; 2.2 Scope of the Reaction; 3 Oxidative Nucleophilic Substitution of Hydrogen; 4 Conversion of sigmaH Adducts into Nitrosoarenes; 5 Introduction of Substituents into Electron-Deficient Heterocycles via Nucleophilic Substitution of Hydrogen; 5.1 Carbon Substituents; 5.2 Hydroxylation; 5.3 Amination; 6 Construction of Heterocyclic Compounds via Nucleophilic Substitution of Hydrogen; 6.1 Indoles; 6.2 Quinolines; 6.3 2,1-Benzisoxazoles; 6.4 Phenazines and Other Heterocyclic Compounds from 2-Nitrosodiphenylamines
6.5 Miscellaneous Syntheses of Heterocycles7 Conclusion; References; Direct Functionalization of C-H Fragments in Nitroarenes as a Synthetic Pathway to Condensed N-Heterocycles; 1 Introduction; 2 Synthesis of Condensed N-heterocycles via Nucleophilic Substitution of Hydrogen (SNH) in Nitroarenes; 2.1 Vicarious Nucleophilic Substitution of Hydrogen; 2.2 Oxidative Nucleophilic Substitution of Hydrogen; 3 Barton-Zard Reaction; 4 Mannich Cyclization of Anionic Adducts of Nitroarenes; 5 Pericyclic Reactions of Nitroarenes; 5.1 [4+2]-Cycloaddition Reactions; 5.2 [3+2]-Cycloaddition Reactions
Summary The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field
Bibliography Includes bibliographical references
Notes English
Print version record
Subject Nucleophilic reactions.
Aromatic compounds.
Aromatic compounds
Nucleophilic reactions
Form Electronic book
Author Charushin, Valery N., editor.
Chupakhin, O. N. (Oleg Nikolaevich), editor.
ISBN 9783319070193
3319070193
3319070185
9783319070186
9783319070209
3319070207
9783319375663
3319375660