Oxidation of C-H Bonds

A combination of oxidation methods and C‒H bond functionalization, this book emphasizes mechanistic understanding and critical analysis of synthetic reactions to offer a guide or manual for practicing chemists. •    Combines oxidation methods and C‒H bond functionalization, two of the most important aspects of organic synthesis •    Deals with C‒H bonds, an area of dynamic and continuous research across chemistry and catalysis •    Helps readers understand the fundamental and applied differences among various oxidation methods and reactions •    Covers mechanistic details, conditions, oxidation reagents, and practical aspects of different reactions

Preface xi 1 Introduction 1 1.1 What Is Oxidation of C—H Bonds? 1 1.2 Chemical Synthesis and Oxidation of C—H Bonds 2 1.3 C—H Bonds 6 1.4 Concepts in This Book 15 References 17 2 Oxidation of Methane 19 2.1 Methane 19 2.2 Methyl sp³ C—H Bond 20 2.3 Oxidations of Methyl sp³ C—H Bond 21 2.4 Summary 35 References 36 3 Oxidation of Alkyl sp³ C—H Bond 39 3.1 Alkane 39 3.2 Alkyl sp³ C—H Bonds 40 3.3 Oxidations of Alkyl sp³ C—H Bond 42 3.4 Summary 61 References 62 4 Oxidation of Alkyl sp³ C—H Bond Assisted by Directing Group 65 4.1 Directing Group 65 4.2 Alkyl sp³ C—H Bonds with Directing Groups 66 4.3 Directed Oxidations of Alkyl sp³ C—H Bond 67 4.4 Summary 97 References 97 5 Oxidation of Alkyl sp³ C—H Bond Adjacent to Unsaturated Carbon Atom 101 5.1 Alkyl α-sp³ C—H Bond 101 5.2 Alkyl sp³ C—H Bonds Adjacent to Unsaturated Carbon Atoms 102 5.3 Oxidations of Alkyl sp³ C—H Bond Adjacent to Unsaturated Carbon Atom 103 5.4 Summary 138 References 138 6 Oxidation of Alkyl sp³ C—H Bond Adjacent to Heteroatom 143 6.1 Alkyl sp³ C—H Bonds Adjacent to Heteroatoms 143 6.2 Oxidations of Alkyl sp³ C—H Bond Adjacent to Heteroatom 144 6.3 Summary 166 References 167 7 Oxidation of Alkenyl or Carbonyl sp² C—H Bond 171 7.1 Alkenyl and Carbonyl sp² C—H Bonds 171 7.2 Oxidations of Alkenyl and Carbonyl sp² C—H Bonds 172 8 Oxidation of Alkynyl spC—H Bond 209 8.1 spC—H Bonds 209 8.2 Oxidations of spC—H Bond 210 8.3 Summary 232 References 232 9 Oxidation of Benzene 235 9.1 Introduction 235 9.2 Oxidations of Phenyl sp2 C—H Bond 237 9.3 Summary 277 References 279 10 Oxidation of Aryl sp² C—H Bond on Substituted Benzene 283 10.1 Introduction 283 10.2 Formation of C—C Bond 284 10.3 Formation of C—N Bond 313 10.4 Formation of C—O Bond 316 10.5 Formation of C—S Bond 322 10.6 Formation of C—Halogen Bond 323 10.7 Summary 331 References 333 11 Oxidation of Aryl sp² C—H Bond Assisted by Directing Group 337 11.1 Introduction 337 11.2 Formation of C—C Bond 337 11.3 Formation of C—N Bond 400 11.4 Formation of C—O Bond 406 11.5 Formation of C—S Bond 412 11.6 Formation of C—Halogen Bond 414 11.7 Summary 424 References 426 12 Oxidation of Aryl sp² C—H Bond on Heteroarene or Perfluoroarene 433 12.1 Introduction 433 12.2 Formation of C—C Bond 434 12.3 Formation of C—N Bond 459 12.4 Formation of C—O Bond 461 12.5 Formation of C—Halogen Bond 462 12.6 Cross-Coupling of Dual Aryl sp² C—H Bonds on Directing-Group-Containing Arenes, Heteroarenes, or Polyfluoroarenes 468 12.7 Summary 477 References 478 13 Oxidative Cross-Coupling of Aryl sp² C—H Bond with Inert C—H Bond 483 13.1 Introduction 483 13.2 Oxidative Coupling of Simple Arenes with Alkanes (Alkylation of Arenes) 484 13.3 Oxidative Coupling of Simple Arenes with Alkenes (Alkenylation of Arenes) 486 13.4 Oxidative Cross-Coupling of Simple Arenes (Arylation of Arenes) 490 13.5 Summary 498 References 499 Index 501