Description
By presenting novel methods for the efficient preparation of fluorinated compounds and their application in pharmaceutical and agrochemical chemistry as well as medicine, this is a valuable source of information for all researchers in academia and industry!
Table of Contents
Preface xiii
1 The Development of New Reagents and Reactions for Synthetic Organofluorine Chemistry by Understanding the Unique Fluorine Effects 1
Qiqiang Xie and Jinbo Hu
1.1 Introduction 1
1.2 The Unique Fluorine Effects in Organic Reactions 3
1.3 The Relationships Among Fluoroalkylation, Fluoroolefination, and Fluorination 9
1.4 Conclusions 20
References 20
2 Perfluoroalkylation Using Perfluorocarboxylic Acids and Anhydrides 23
Shintaro Kawamura and Mikiko Sodeoka
2.1 Introduction 23
2.2 Perfluoroalkylation with Perfluorocarboxylic Acids 23
2.3 Perfluoroalkylation with Perfluorocarboxylic Anhydride 39
2.4 Summary and Prospects 43
References 43
3 Chemistry of OCF3, SCF3, and SeCF3 Functional Groups 49
Fabien Toulgoat, François Liger and Thierry Billard
3.1 Introduction 49
3.2 CF3O Chemistry 49
3.3 CF3S Chemistry 63
3.4 CF3Se Chemistry 69
3.5 Summary and Conclusions 85
References 86
4 Introduction of Trifluoromethylthio Group into Organic Molecules 99
Hangming Ge, He Liu and Qilong Shen
4.1 Introduction 99
4.2 Nucleophilic Trifluoromethylthiolation 99
4.3 Electrophilic Trifluoromethylthiolating Reagents 120
4.4 Radical Trifluoromethylthiolation 151
4.5 Summary and Prospect 165
References 165
5 Bifunctionalization-Based Catalytic Fluorination and Trifluoromethylation 173
Pinhong Chen and Guosheng Liu
5.1 Introduction 173
5.2 Palladium-Catalyzed Fluorination, Trifluoromethylation, and Trifluoromethoxylation of Alkenes 173
5.3 Copper-Catalyzed Trifluoromethylative Functionalization of Alkenes 183
5.4 Summary and Conclusions 197
References 197
6 Fluorination, Trifluoromethylation, and Trifluoromethylthiolation of Alkenes, Cyclopropanes, and Diazo Compounds 201
Kálmán J. Szabó
6.1 Introduction 201
6.2 Fluorination of Alkenes, Cyclopropanes, and Diazocarbonyl Compounds 202
6.3 Fluorination-Based Bifunctionalization of Diazocarbonyl Compounds 209
6.4 Trifluoromethylation of Alkenes, Alkynes, and Diazocarbonyl Compounds with the Togni Reagent 212
6.5 Bifunctionalization-Based Trifluoromethylthiolation of Diazocarbonyl Compounds 218
6.6 Summary 220
References 221
7 Photoredox Catalysis in Fluorination and Trifluoromethylation Reactions 225
Takashi Koike and Munetaka Akita
7.1 Introduction 225
7.2 Fluorination 226
7.3 Trifluoromethylation 234
7.4 Summary and Outlook 239
References 239
8 Asymmetric Fluorination Reactions 241
Edward Miller and F. Dean Toste
8.1 Introduction 241
8.2 Electrophilic Fluorination 242
8.3 Nucleophilic Fluorination 269
8.4 Summary and Conclusions 274
References 276
9 The Self-Disproportionation of Enantiomers (SDE): Fluorine as an SDE-Phoric Substituent 281
Jianlin Han, Santos Fustero, Hiroki Moriwaki, Alicja Wzorek, Vadim A. Soloshonok and Karel D. Klika
9.1 Introduction 281
9.2 General Concepts and the Role of Fluorine in the Manifestation of the SDE 283
9.3 The SDE Phenomenon 285
9.4 The SIDA Phenomenon 294
9.5 Conclusions and Recommendations 296
References 299
10 DFT Modeling of Catalytic Fluorination Reactions: Mechanisms, Reactivities, and Selectivities 307
Yueqian Sang, Biying Zhou, Meng-Meng Zheng, Xiao-Song Xue and Jin-Pei Cheng
10.1 Introduction 307
10.2 DFT Modeling of Transition Metal-Catalyzed Fluorination Reactions 308
10.3 DFT Modeling of Organocatalytic Fluorination Reactions 340
10.4 DFT Modeling of Enzymatic Fluorination Reaction 354
10.5 Conclusions 357
Acknowledgments 357
References 358
11 Current Trends in the Design of Fluorine-Containing Agrochemicals 363
Peter Jeschke
11.1 Introduction 363
11.2 Role of Fluorine in the Design of Modern Agrochemicals 363
11.3 Fluorinated Modern Agrochemicals 365
11.4 Summary and Prospects 389
References 390
12 Precision Radiochemistry for Fluorine-18 Labeling of PET Tracers 397
Jian Rong, Ahmed Haider and Steven Liang
12.1 Introduction 397
12.2 Electrophilic 18F-Fluorination with [18F]F2 and [18F]F2-Derived Reagents 398
12.3 Nucleophilic Aliphatic 18F-Fluorination 399
12.4 Nucleophilic Aromatic 18F-Fluorination with [18F]Fluoride 405
12.5 18F-Labeling of Multifluoromethyl Motifs with [18F]Fluoride 418
12.6 Summary and Conclusions 421
References 421
Index 427
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