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Full Description
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
Contents
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
