Oxidation of C-H Bonds

Wenjun Lu, D.Eng., is a Professor of Organic Chemistry at Shanghai Jiao Tong University.Lihong Zhou, PhD, is a Research Associate at Shanghai Jiao Tong University.

• Preface xi1 Introduction 11.1 What Is Oxidation of C—H Bonds? 11.2 Chemical Synthesis and Oxidation of C—H Bonds 21.3 C—H Bonds 61.4 Concepts in This Book 15References 172 Oxidation of Methane 192.1 Methane 192.2 Methyl sp³ C—H Bond 202.3 Oxidations of Methyl sp³ C—H Bond 212.4 Summary 35References 363 Oxidation of Alkyl sp³ C—H Bond 393.1 Alkane 393.2 Alkyl sp³ C—H Bonds 403.3 Oxidations of Alkyl sp³ C—H Bond 423.4 Summary 61References 624 Oxidation of Alkyl sp³ C—H Bond Assisted by Directing Group 654.1 Directing Group 654.2 Alkyl sp³ C—H Bonds with Directing Groups 664.3 Directed Oxidations of Alkyl sp³ C—H Bond 674.4 Summary 97References 975 Oxidation of Alkyl sp³ C—H Bond Adjacent to Unsaturated Carbon Atom 1015.1 Alkyl α-sp³ C—H Bond 1015.2 Alkyl sp³ C—H Bonds Adjacent to Unsaturated Carbon Atoms 1025.3 Oxidations of Alkyl sp³ C—H Bond Adjacent to Unsaturated Carbon Atom 1035.4 Summary 138References 1386 Oxidation of Alkyl sp³ C—H Bond Adjacent to Heteroatom 1436.1 Alkyl sp³ C—H Bonds Adjacent to Heteroatoms 1436.2 Oxidations of Alkyl sp³ C—H Bond Adjacent to Heteroatom 1446.3 Summary 166References 1677 Oxidation of Alkenyl or Carbonyl sp² C—H Bond 1717.1 Alkenyl and Carbonyl sp² C—H Bonds 1717.2 Oxidations of Alkenyl and Carbonyl sp² C—H Bonds 1728 Oxidation of Alkynyl spC—H Bond 2098.1 spC—H Bonds 2098.2 Oxidations of spC—H Bond 2108.3 Summary 232References 2329 Oxidation of Benzene 2359.1 Introduction 2359.2 Oxidations of Phenyl sp2 C—H Bond 2379.3 Summary 277References 27910 Oxidation of Aryl sp² C—H Bond on Substituted Benzene 28310.1 Introduction 28310.2 Formation of C—C Bond 28410.3 Formation of C—N Bond 31310.4 Formation of C—O Bond 31610.5 Formation of C—S Bond 32210.6 Formation of C—Halogen Bond 32310.7 Summary 331References 33311 Oxidation of Aryl sp² C—H Bond Assisted by Directing Group 33711.1 Introduction 33711.2 Formation of C—C Bond 33711.3 Formation of C—N Bond 40011.4 Formation of C—O Bond 40611.5 Formation of C—S Bond 41211.6 Formation of C—Halogen Bond 41411.7 Summary 424References 42612 Oxidation of Aryl sp² C—H Bond on Heteroarene or Perfluoroarene 43312.1 Introduction 43312.2 Formation of C—C Bond 43412.3 Formation of C—N Bond 45912.4 Formation of C—O Bond 46112.5 Formation of C—Halogen Bond 46212.6 Cross-Coupling of Dual Aryl sp² C—H Bonds on Directing-Group-Containing Arenes, Heteroarenes, or Polyfluoroarenes 46812.7 Summary 477References 47813 Oxidative Cross-Coupling of Aryl sp² C—H Bond with Inert C—H Bond 48313.1 Introduction 48313.2 Oxidative Coupling of Simple Arenes with Alkanes (Alkylation of Arenes) 48413.3 Oxidative Coupling of Simple Arenes with Alkenes (Alkenylation of Arenes) 48613.4 Oxidative Cross-Coupling of Simple Arenes (Arylation of Arenes) 49013.5 Summary 498References 499Index 501