{"product_id":"organofluorine-chemistry-synthesis-modeling-and-applications-9783527347117","title":"Organofluorine Chemistry: Synthesis, Modeling, and Applications","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003eBy 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!\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003ePreface xiii\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 The Development of New Reagents and Reactions for Synthetic Organofluorine Chemistry by Understanding the Unique Fluorine Effects \u003c\/b\u003e\u003cb\u003e1\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eQiqiang Xie and Jinbo Hu\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e1.1 Introduction 1\u003c\/p\u003e \u003cp\u003e1.2 The Unique Fluorine Effects in Organic Reactions 3\u003c\/p\u003e \u003cp\u003e1.2.1 Fluorine-Enabled Stability of “CuCF3” inWater, and the Unusual Water-Promoted Trifluoromethylation 3\u003c\/p\u003e \u003cp\u003e1.2.2 Fluorine Enables β-Fluoride Elimination of Organocopper Species 4\u003c\/p\u003e \u003cp\u003e1.2.3 The “Negative Fluorine Effect” Facilitates the α-Elimination of Fluorocarbanions to Generate Difluorocarbene Species 5\u003c\/p\u003e \u003cp\u003e1.2.4 Tackling the β-Fluoride Elimination of Trifluoromethoxide Anion via a Fluoride Ion-Mediated Process 9\u003c\/p\u003e \u003cp\u003e1.3 The Relationships Among Fluoroalkylation, Fluoroolefination, and Fluorination 9\u003c\/p\u003e \u003cp\u003e1.3.1 From Fluoroalkylation to Fluoroolefination 9\u003c\/p\u003e \u003cp\u003e1.3.2 From Fluoroolefination to Fluoroalkylation 13\u003c\/p\u003e \u003cp\u003e1.3.3 From Fluoroalkylation to Fluorination 18\u003c\/p\u003e \u003cp\u003e1.4 Conclusions 20\u003c\/p\u003e \u003cp\u003eReferences 20\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Perfluoroalkylation Using Perfluorocarboxylic Acids and Anhydrides \u003c\/b\u003e\u003cb\u003e23\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eShintaro Kawamura and Mikiko Sodeoka\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e2.1 Introduction 23\u003c\/p\u003e \u003cp\u003e2.2 Perfluoroalkylation with Perfluorocarboxylic Acids 23\u003c\/p\u003e \u003cp\u003e2.2.1 Electrochemical Reactions 24\u003c\/p\u003e \u003cp\u003e2.2.1.1 Reactions of Alkenes and Alkynes 24\u003c\/p\u003e \u003cp\u003e2.2.1.2 Reaction of Aromatic Compounds 30\u003c\/p\u003e \u003cp\u003e2.2.2 Reactions Using XeF\u003csub\u003e2\u003c\/sub\u003e 30\u003c\/p\u003e \u003cp\u003e2.2.3 Reactions Using Copper and Silver Salts 31\u003c\/p\u003e \u003cp\u003e2.2.3.1 Using Copper Salts 31\u003c\/p\u003e \u003cp\u003e2.2.3.2 Using Silver Salts 35\u003c\/p\u003e \u003cp\u003e2.2.4 Photochemical Reactions 36\u003c\/p\u003e \u003cp\u003e2.2.5 Other Methods 38\u003c\/p\u003e \u003cp\u003e2.2.5.1 Hydro-Trifluoromethylation of Fullerene 38\u003c\/p\u003e \u003cp\u003e2.2.5.2 Metal-Free Aryldifluoromethylation Using S\u003csub\u003e2\u003c\/sub\u003eO\u003csub\u003e8\u003c\/sub\u003e \u003csup\u003e2−\u003c\/sup\u003e 39\u003c\/p\u003e \u003cp\u003e2.3 Perfluoroalkylation with Perfluorocarboxylic Anhydride 39\u003c\/p\u003e \u003cp\u003e2.3.1 Reactions Using Perfluorocarboxylic Anhydride\/Urea⋅H\u003csub\u003e2\u003c\/sub\u003eO\u003csub\u003e2\u003c\/sub\u003e 40\u003c\/p\u003e \u003cp\u003e2.3.2 Photocatalytic Reactions Using Perfluorocarboxylic Anhydride\/Pyridine \u003ci\u003eN\u003c\/i\u003e-oxide 42\u003c\/p\u003e \u003cp\u003e2.4 Summary and Prospects 43\u003c\/p\u003e \u003cp\u003eReferences 43\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Chemistry of OCF\u003csub\u003e3\u003c\/sub\u003e, SCF\u003csub\u003e3\u003c\/sub\u003e, and SeCF\u003csub\u003e3\u003c\/sub\u003e Functional Groups \u003c\/b\u003e\u003cb\u003e49\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eFabien Toulgoat, François Liger and Thierry Billard\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction 49\u003c\/p\u003e \u003cp\u003e3.2 CF\u003csub\u003e3\u003c\/sub\u003eO Chemistry 49\u003c\/p\u003e \u003cp\u003e3.2.1 De Novo Construction 49\u003c\/p\u003e \u003cp\u003e3.2.1.1 Trifluorination of Alcohol Derivatives 49\u003c\/p\u003e \u003cp\u003e3.2.1.2 Fluorination of Difluorinated Compounds 50\u003c\/p\u003e \u003cp\u003e3.2.2 Indirect Methods 51\u003c\/p\u003e \u003cp\u003e3.2.2.1 \u003ci\u003eO\u003c\/i\u003e-(Trifluoromethyl)dibenzofuranium Salts 51\u003c\/p\u003e \u003cp\u003e3.2.2.2 Hypervalent Iodine Trifluoromethylation Reagents 51\u003c\/p\u003e \u003cp\u003e3.2.2.3 CF\u003csub\u003e3\u003c\/sub\u003eSiMe\u003csub\u003e3\u003c\/sub\u003e 51\u003c\/p\u003e \u003cp\u003e3.2.3 Direct Trifluoromethoxylation 52\u003c\/p\u003e \u003cp\u003e3.2.3.1 Difluorophosgene and Derivatives 53\u003c\/p\u003e \u003cp\u003e3.2.3.2 Trifluoromethyl Hypofluorite and Derivatives 53\u003c\/p\u003e \u003cp\u003e3.2.3.3 Trifluoromethyl Triflate (TFMT) 53\u003c\/p\u003e \u003cp\u003e3.2.3.4 Trifluoromethoxide Salts Derived from TFMT or Difluorophosgene 55\u003c\/p\u003e \u003cp\u003e3.2.3.5 Trifluoromethyl Arylsulfonates (TFMSs) 57\u003c\/p\u003e \u003cp\u003e3.2.3.6 Trifluoromethylbenzoate (TFBz) 60\u003c\/p\u003e \u003cp\u003e3.2.3.7 2,4-Dinitro(trifluoromethoxy)benzene (DNTFB) 60\u003c\/p\u003e \u003cp\u003e3.2.3.8 (Triphenylphosphonio)difluoroacetate (PDFA) 61\u003c\/p\u003e \u003cp\u003e3.2.3.9 \u003ci\u003eN\u003c\/i\u003e-Trifluoromethoxylated Reagents 62\u003c\/p\u003e \u003cp\u003e3.3 CF\u003csub\u003e3\u003c\/sub\u003eS Chemistry 63\u003c\/p\u003e \u003cp\u003e3.3.1 Indirect Methods 63\u003c\/p\u003e \u003cp\u003e3.3.2 Direct Trifluoromethylthiolation 64\u003c\/p\u003e \u003cp\u003e3.3.2.1 CF\u003csub\u003e3\u003c\/sub\u003eSAg, CF\u003csub\u003e3\u003c\/sub\u003eSCu, CF\u003csub\u003e3\u003c\/sub\u003eSNR\u003csub\u003e4\u003c\/sub\u003e 65\u003c\/p\u003e \u003cp\u003e3.3.2.2 Trifluoromethanesulfenamides 65\u003c\/p\u003e \u003cp\u003e3.3.2.3 \u003ci\u003eN\u003c\/i\u003e-Trifluoromethylthiophthalimide 66\u003c\/p\u003e \u003cp\u003e3.3.2.4 \u003ci\u003eN\u003c\/i\u003e-Trifluoromethylthiosaccharin 67\u003c\/p\u003e \u003cp\u003e3.3.2.5 \u003ci\u003eN\u003c\/i\u003e-Trifluoromethylthiobis(phenylsulfonyl)amide 68\u003c\/p\u003e \u003cp\u003e3.4 CF\u003csub\u003e3\u003c\/sub\u003eSe Chemistry 69\u003c\/p\u003e \u003cp\u003e3.4.1 Introduction 69\u003c\/p\u003e \u003cp\u003e3.4.2 Indirect Synthesis of CF\u003csub\u003e3\u003c\/sub\u003eSe Moiety 70\u003c\/p\u003e \u003cp\u003e3.4.2.1 Ruppert–Prakash Reagent (CF\u003csub\u003e3\u003c\/sub\u003eSiMe\u003csub\u003e3\u003c\/sub\u003e) 71\u003c\/p\u003e \u003cp\u003e3.4.2.2 Fluoroform (HCF\u003csub\u003e3\u003c\/sub\u003e) 72\u003c\/p\u003e \u003cp\u003e3.4.2.3 Other Reagents Involved in CF\u003csub\u003e3\u003c\/sub\u003e \u003csup\u003e−\u003c\/sup\u003e Anion Generation 73\u003c\/p\u003e \u003cp\u003e3.4.2.4 Sodium Trifluoromethylsulfinate (CF\u003csub\u003e3\u003c\/sub\u003eSO\u003csub\u003e2\u003c\/sub\u003eNa) 73\u003c\/p\u003e \u003cp\u003e3.4.3 Direct Introduction of the CF\u003csub\u003e3\u003c\/sub\u003eSe Moiety 74\u003c\/p\u003e \u003cp\u003e3.4.3.1 Trifluoromethyl Selenocopper DMF Complex 74\u003c\/p\u003e \u003cp\u003e3.4.3.2 Trifluoromethyl Selenocopper Bipyridine Complex: [bpyCuSeCF\u003csub\u003e3\u003c\/sub\u003e]\u003csub\u003e2\u003c\/sub\u003e 75\u003c\/p\u003e \u003cp\u003e3.4.3.3 Tetramethylammonium Trifluoromethylselenolate [(NMe\u003csub\u003e4\u003c\/sub\u003e)(SeCF\u003csub\u003e3\u003c\/sub\u003e)] 76\u003c\/p\u003e \u003cp\u003e3.4.3.4 \u003ci\u003eIn Situ \u003c\/i\u003eGeneration of CF\u003csub\u003e3\u003c\/sub\u003eSe− Anion from Elemental Selenium 79\u003c\/p\u003e \u003cp\u003e3.4.3.5 Trifluoromethylselenyl Chloride (CF\u003csub\u003e3\u003c\/sub\u003eSeCl) 80\u003c\/p\u003e \u003cp\u003e3.4.3.6 Benzyltrifluoromethylselenide (CF\u003csub\u003e3\u003c\/sub\u003eSeBn) 81\u003c\/p\u003e \u003cp\u003e3.4.3.7 Trifluoromethylselenotoluenesulfonate (CF\u003csub\u003e3\u003c\/sub\u003eSeTs) 83\u003c\/p\u003e \u003cp\u003e3.4.3.8 Benzylthiazolium Salt BT-SeCF\u003csub\u003e3\u003c\/sub\u003e 85\u003c\/p\u003e \u003cp\u003e3.5 Summary and Conclusions 85\u003c\/p\u003e \u003cp\u003eReferences 86\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Introduction of Trifluoromethylthio Group into Organic Molecules \u003c\/b\u003e\u003cb\u003e99\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eHangming Ge, He Liu and Qilong Shen\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction 99\u003c\/p\u003e \u003cp\u003e4.2 Nucleophilic Trifluoromethylthiolation 99\u003c\/p\u003e \u003cp\u003e4.2.1 Preparation of Nucleophilic Trifluoromethylthiolating Reagent 99\u003c\/p\u003e \u003cp\u003e4.2.1.1 Preparation of Hg(SCF\u003csub\u003e3\u003c\/sub\u003e)\u003csub\u003e2\u003c\/sub\u003e, AgSCF\u003csub\u003e3\u003c\/sub\u003e, and CuSCF\u003csub\u003e3\u003c\/sub\u003e 99\u003c\/p\u003e \u003cp\u003e4.2.1.2 Preparation of MSCF\u003csub\u003e3\u003c\/sub\u003e (M = K, Cs, Me\u003csub\u003e4\u003c\/sub\u003eN, and S(NMe\u003csub\u003e2\u003c\/sub\u003e)\u003csub\u003e3\u003c\/sub\u003e) 100\u003c\/p\u003e \u003cp\u003e4.2.1.3 Preparation of Stable Trifluoromethylthiolated Copper(I) Complexes 100\u003c\/p\u003e \u003cp\u003e4.2.2 Formation of C(sp\u003csup\u003e2\u003c\/sup\u003e)-SCF\u003csub\u003e3\u003c\/sub\u003e by Nucleophilic Trifluoromethylthiolating Reagents 101\u003c\/p\u003e \u003cp\u003e4.2.2.1 Reaction of CuSCF\u003csub\u003e3\u003c\/sub\u003e with Aryl Halides 101\u003c\/p\u003e \u003cp\u003e4.2.2.2 Sandmeyer-Type Trifluoromethylthiolation 102\u003c\/p\u003e \u003cp\u003e4.2.2.3 Transition Metal-Catalyzed Trifluoromethylthiolation 103\u003c\/p\u003e \u003cp\u003e4.2.2.4 Oxidative Trifluoromethylthiolation 107\u003c\/p\u003e \u003cp\u003e4.2.2.5 Transition Metal-Catalyzed Trifluoromethylthiolation of Arenes via C–H Activation 108\u003c\/p\u003e \u003cp\u003e4.2.2.6 Miscellaneous Methods for the Formation or Aryl Trifluoromethylthioethers via Nucleophilic Trifluoromethylthiolating Reagents 110\u003c\/p\u003e \u003cp\u003e4.2.3 Formation of C(sp\u003csup\u003e3\u003c\/sup\u003e)-SCF\u003csub\u003e3\u003c\/sub\u003e by Nucleophilic Trifluoromethylthiolating Reagents 112\u003c\/p\u003e \u003cp\u003e4.2.3.1 Reaction of CuSCF\u003csub\u003e3\u003c\/sub\u003e with Activated Alkylated Halides 112\u003c\/p\u003e \u003cp\u003e4.2.3.2 Reaction of MSCF\u003csub\u003e3\u003c\/sub\u003e with Unactivated Alkyl Halides 114\u003c\/p\u003e \u003cp\u003e4.2.3.3 Nucleophilic Dehydroxytrifluoromethylthiolation of Alcohols 114\u003c\/p\u003e \u003cp\u003e4.2.3.4 Nucleophilic Trifluoromethylthiolation of Alcohol Derivatives 116\u003c\/p\u003e \u003cp\u003e4.2.3.5 Nucleophilic Trifluoromethylthiolation of α-Diazoesters 116\u003c\/p\u003e \u003cp\u003e4.2.3.6 Formation or Alkyl Trifluoromethylthioethers via \u003ci\u003eIn Situ \u003c\/i\u003eGenerated Nucleophilic Trifluoromethylthiolating Reagent 118\u003c\/p\u003e \u003cp\u003e4.2.3.7 Formation of Alkyl Trifluoromethylthioethers via C—H Bond Trifluoromethylthiolation 120\u003c\/p\u003e \u003cp\u003e4.3 Electrophilic Trifluoromethylthiolating Reagents 120\u003c\/p\u003e \u003cp\u003e4.3.1 CF\u003csub\u003e3\u003c\/sub\u003eSCl 120\u003c\/p\u003e \u003cp\u003e4.3.2 CF\u003csub\u003e3\u003c\/sub\u003eSSCF\u003csub\u003e3\u003c\/sub\u003e 121\u003c\/p\u003e \u003cp\u003e4.3.3 Haas Reagent 121\u003c\/p\u003e \u003cp\u003e4.3.4 Munavalli Reagent 123\u003c\/p\u003e \u003cp\u003e4.3.5 Billard Reagent 128\u003c\/p\u003e \u003cp\u003e4.3.6 Shen Reagent 131\u003c\/p\u003e \u003cp\u003e4.3.7 Shen Reagent-II 136\u003c\/p\u003e \u003cp\u003e4.3.8 Optically Active Pure Trifluoromethylthiolation Reagents 140\u003c\/p\u003e \u003cp\u003e4.3.9 Lu–Shen Reagent 141\u003c\/p\u003e \u003cp\u003e4.3.10 α-Cumyl Bromodifluoromethanesulfenate 144\u003c\/p\u003e \u003cp\u003e4.3.11 Shibata Reagent 145\u003c\/p\u003e \u003cp\u003e4.3.12 \u003ci\u003eIn Situ\u003c\/i\u003e-Generated Electrophilic Trifluoromethylthiolating Reagents 146\u003c\/p\u003e \u003cp\u003e4.3.12.1 AgSCF\u003csub\u003e3\u003c\/sub\u003e +TCCA 146\u003c\/p\u003e \u003cp\u003e4.3.12.2 AgSCF\u003csub\u003e3\u003c\/sub\u003e +NCS 148\u003c\/p\u003e \u003cp\u003e4.3.12.3 Langlois Reagent (CF\u003csub\u003e3\u003c\/sub\u003eSO\u003csub\u003e2\u003c\/sub\u003eNa) with Phosphorus Reductants 148\u003c\/p\u003e \u003cp\u003e4.3.12.4 Use of CF\u003csub\u003e3\u003c\/sub\u003eSO\u003csub\u003e2\u003c\/sub\u003eCl with Phosphorus Reductants 149\u003c\/p\u003e \u003cp\u003e4.3.12.5 Reagent Based on CF\u003csub\u003e3\u003c\/sub\u003eSOCl and Phosphorus Reductants 151\u003c\/p\u003e \u003cp\u003e4.4 Radical Trifluoromethylthiolation 151\u003c\/p\u003e \u003cp\u003e4.4.1 Trifluoromethylthiolation by AgSCF\u003csub\u003e3\u003c\/sub\u003e\/S\u003csub\u003e2\u003c\/sub\u003eO\u003csub\u003e8\u003c\/sub\u003e \u003csup\u003e2−\u003c\/sup\u003e 152\u003c\/p\u003e \u003cp\u003e4.4.2 Electrophilic Reagents Involved in Radical Trifluoromethylthiolation 158\u003c\/p\u003e \u003cp\u003e4.4.3 Visible Light-Promoted Trifluoromethylthiolation by Using Electrophilic Reagents 159\u003c\/p\u003e \u003cp\u003e4.5 Summary and Prospect 165\u003c\/p\u003e \u003cp\u003eReferences 165\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Bifunctionalization-Based Catalytic Fluorination and Trifluoromethylation \u003c\/b\u003e\u003cb\u003e173\u003cbr\u003e\u003c\/b\u003e\u003ci\u003ePinhong Chen and Guosheng Liu\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction 173\u003c\/p\u003e \u003cp\u003e5.2 Palladium-Catalyzed Fluorination, Trifluoromethylation, and Trifluoromethoxylation of Alkenes 173\u003c\/p\u003e \u003cp\u003e5.2.1 Palladium-Catalyzed Fluorination of Alkenes 174\u003c\/p\u003e \u003cp\u003e5.2.2 Palladium-Catalyzed Trifluoromethylation of Alkenes 179\u003c\/p\u003e \u003cp\u003e5.2.3 Palladium-Catalyzed Trifluoromethoxylation of Alkenes 180\u003c\/p\u003e \u003cp\u003e5.3 Copper-Catalyzed Trifluoromethylative Functionalization of Alkenes 183\u003c\/p\u003e \u003cp\u003e5.3.1 Copper-Catalyzed Trifluoromethylamination of Alkenes 184\u003c\/p\u003e \u003cp\u003e5.3.2 Copper-Catalyzed Trifluoromethyloxygenation of Alkenes 185\u003c\/p\u003e \u003cp\u003e5.3.3 Copper-Catalyzed Trifluoromethylcarbonation of Alkenes 187\u003c\/p\u003e \u003cp\u003e5.3.4 Enantioselective Copper-Catalyzed Trifluoromethylation of Alkenes 190\u003c\/p\u003e \u003cp\u003e5.4 Summary and Conclusions 197\u003c\/p\u003e \u003cp\u003eReferences 197\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Fluorination, Trifluoromethylation, and Trifluoromethylthiolation of Alkenes, Cyclopropanes, and Diazo Compounds \u003c\/b\u003e\u003cb\u003e201\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eKálmán J. Szabó\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction 201\u003c\/p\u003e \u003cp\u003e6.2 Fluorination of Alkenes, Cyclopropanes, and Diazocarbonyl Compounds 202\u003c\/p\u003e \u003cp\u003e6.2.1 Application of Fluoro-Benziodoxole for Fluorination of Alkenes 202\u003c\/p\u003e \u003cp\u003e6.2.1.1 Geminal Difluorination of Styrene Derivatives 203\u003c\/p\u003e \u003cp\u003e6.2.1.2 Iodofluorination of Alkenes 205\u003c\/p\u003e \u003cp\u003e6.2.1.3 Fluorocyclization with C—N, C—O, and C—C Bond Formation 205\u003c\/p\u003e \u003cp\u003e6.2.2 Fluorinative Cyclopropane Opening 207\u003c\/p\u003e \u003cp\u003e6.2.3 Fluorine-18 Labeling with Fluorobenziodoxole 207\u003c\/p\u003e \u003cp\u003e6.3 Fluorination-Based Bifunctionalization of Diazocarbonyl Compounds 209\u003c\/p\u003e \u003cp\u003e6.3.1 Rhodium-Catalyzed Geminal Oxyfluorination Reactions 209\u003c\/p\u003e \u003cp\u003e6.3.2 [\u003csup\u003e18\u003c\/sup\u003eF]Fluorobenziodoxole for Synthesis of α-Fluoro Ethers 210\u003c\/p\u003e \u003cp\u003e6.4 Trifluoromethylation of Alkenes, Alkynes, and Diazocarbonyl Compounds with the Togni Reagent 212\u003c\/p\u003e \u003cp\u003e6.4.1 Bifunctionalization of C—C Multiple Bonds 213\u003c\/p\u003e \u003cp\u003e6.4.1.1 Oxytrifluoromethylation of Alkenes and Alkynes 213\u003c\/p\u003e \u003cp\u003e6.4.1.2 Cyanotrifluoromethylation of Styrenes 214\u003c\/p\u003e \u003cp\u003e6.4.1.3 C–H Trifluoromethylation of Benzoquinone Derivatives 215\u003c\/p\u003e \u003cp\u003e6.4.2 Geminal Oxytrifluoromethylation of Diazocarbonyl Compounds 217\u003c\/p\u003e \u003cp\u003e6.5 Bifunctionalization-Based Trifluoromethylthiolation of Diazocarbonyl Compounds 218\u003c\/p\u003e \u003cp\u003e6.5.1 Multicomponent Approach for Geminal Oxy-Trifluormethylthiolation 218\u003c\/p\u003e \u003cp\u003e6.5.2 Simultaneous Formation of C—C and C—SCF\u003csub\u003e3\u003c\/sub\u003e Bonds via Hooz-Type Reaction 219\u003c\/p\u003e \u003cp\u003e6.6 Summary 220\u003c\/p\u003e \u003cp\u003eReferences 221\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Photoredox Catalysis in Fluorination and Trifluoromethylation Reactions \u003c\/b\u003e\u003cb\u003e225\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eTakashi Koike and Munetaka Akita\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction 225\u003c\/p\u003e \u003cp\u003e7.2 Fluorination 226\u003c\/p\u003e \u003cp\u003e7.2.1 Fluorination Through Direct HAT Process by Excited Photocatalyst 226\u003c\/p\u003e \u003cp\u003e7.2.2 Fluorination Through Photoredox Processes 228\u003c\/p\u003e \u003cp\u003e7.3 Trifluoromethylation 234\u003c\/p\u003e \u003cp\u003e7.3.1 Trifluoromethylation of Aromatic Compounds 234\u003c\/p\u003e \u003cp\u003e7.3.2 Trifluoromethylative Substitution of Alkyl Bromides 238\u003c\/p\u003e \u003cp\u003e7.4 Summary and Outlook 239\u003c\/p\u003e \u003cp\u003eReferences 239\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Asymmetric Fluorination Reactions \u003c\/b\u003e\u003cb\u003e241\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eEdward Miller and F. Dean Toste\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction 241\u003c\/p\u003e \u003cp\u003e8.2 Electrophilic Fluorination 242\u003c\/p\u003e \u003cp\u003e8.2.1 Stoichiometric Asymmetric Fluorination 242\u003c\/p\u003e \u003cp\u003e8.2.1.1 Chiral Auxiliary 242\u003c\/p\u003e \u003cp\u003e8.2.1.2 Chiral Reagents 243\u003c\/p\u003e \u003cp\u003e8.2.2 Catalytic Electrophilic Fluorination 244\u003c\/p\u003e \u003cp\u003e8.2.2.1 Organocatalytic Fluorination 244\u003c\/p\u003e \u003cp\u003e8.2.2.2 Transition Metal-Catalyzed Fluorinations 259\u003c\/p\u003e \u003cp\u003e8.3 Nucleophilic Fluorination 269\u003c\/p\u003e \u003cp\u003e8.3.1 Metal-Catalyzed Nucleophilic Fluorination 270\u003c\/p\u003e \u003cp\u003e8.3.1.1 Ring Opening of Strained Ring Systems 270\u003c\/p\u003e \u003cp\u003e8.3.1.2 Allylic Functionalization 272\u003c\/p\u003e \u003cp\u003e8.3.2 Organocatalytic Nucleophilic Fluorination 273\u003c\/p\u003e \u003cp\u003e8.4 Summary and Conclusions 274\u003c\/p\u003e \u003cp\u003eReferences 276\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 The Self-Disproportionation of Enantiomers (SDE): Fluorine as an SDE-Phoric Substituent \u003c\/b\u003e\u003cb\u003e281\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eJianlin Han, Santos Fustero, Hiroki Moriwaki, Alicja Wzorek, Vadim A. Soloshonok and Karel D. Klika\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction 281\u003c\/p\u003e \u003cp\u003e9.2 General Concepts and the Role of Fluorine in the Manifestation of the SDE 283\u003c\/p\u003e \u003cp\u003e9.3 The SDE Phenomenon 285\u003c\/p\u003e \u003cp\u003e9.3.1 SDE via Distillation 285\u003c\/p\u003e \u003cp\u003e9.3.2 SDE via Sublimation 286\u003c\/p\u003e \u003cp\u003e9.3.3 SDE via Chromatography 288\u003c\/p\u003e \u003cp\u003e9.3.3.1 SDEvC for Compounds Containing a –CF\u003csub\u003e3\u003c\/sub\u003e Moiety 289\u003c\/p\u003e \u003cp\u003e9.3.3.2 SDEvC for Compounds Containing a C\u003csub\u003eq\u003c\/sub\u003e–F\u003csub\u003e1\/2\u003c\/sub\u003e Moiety 290\u003c\/p\u003e \u003cp\u003e9.3.3.3 SDEvC for Compounds Containing a –COCF\u003csub\u003e3\u003c\/sub\u003e Moiety 291\u003c\/p\u003e \u003cp\u003e9.4 The SIDA Phenomenon 294\u003c\/p\u003e \u003cp\u003e9.5 Conclusions and Recommendations 296\u003c\/p\u003e \u003cp\u003eReferences 299\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 DFT Modeling of Catalytic Fluorination Reactions: Mechanisms, Reactivities, and Selectivities \u003c\/b\u003e\u003cb\u003e307\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eYueqian Sang, Biying Zhou, Meng-Meng Zheng, Xiao-Song Xue and Jin-Pei Cheng\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction 307\u003c\/p\u003e \u003cp\u003e10.2 DFT Modeling of Transition Metal-Catalyzed Fluorination Reactions 308\u003c\/p\u003e \u003cp\u003e10.2.1 Ti-Catalyzed Fluorination Reaction 308\u003c\/p\u003e \u003cp\u003e10.2.2 Mn-Catalyzed Fluorination Reactions 309\u003c\/p\u003e \u003cp\u003e10.2.3 Fe-Catalyzed Fluorination Reactions 310\u003c\/p\u003e \u003cp\u003e10.2.4 Rh-Catalyzed Fluorination Reactions 312\u003c\/p\u003e \u003cp\u003e10.2.5 Ir-Catalyzed Fluorination Reactions 316\u003c\/p\u003e \u003cp\u003e10.2.6 Pd-Catalyzed Fluorination Reactions 317\u003c\/p\u003e \u003cp\u003e10.2.6.1 Pd-Catalyzed Nucleophilic Fluorination 317\u003c\/p\u003e \u003cp\u003e10.2.6.2 Pd-Catalyzed Electrophilic Fluorination 322\u003c\/p\u003e \u003cp\u003e10.2.7 Cu-Catalyzed Fluorination Reactions 328\u003c\/p\u003e \u003cp\u003e10.2.7.1 Cu-Catalyzed Nucleophilic Fluorination 328\u003c\/p\u003e \u003cp\u003e10.2.7.2 Cu-Mediated Radical Fluorination 331\u003c\/p\u003e \u003cp\u003e10.2.8 Ag-Catalyzed Fluorination Reactions 333\u003c\/p\u003e \u003cp\u003e10.2.9 Zn-Catalyzed Fluorination Reactions 339\u003c\/p\u003e \u003cp\u003e10.3 DFT Modeling of Organocatalytic Fluorination Reactions 340\u003c\/p\u003e \u003cp\u003e10.3.1 Fluorination Reactions Catalyzed by Chiral Amines 340\u003c\/p\u003e \u003cp\u003e10.3.1.1 Chiral Secondary Amines-Catalyzed Fluorination Reactions 340\u003c\/p\u003e \u003cp\u003e10.3.1.2 Chiral Primary Amines-Catalyzed Fluorination Reactions 342\u003c\/p\u003e \u003cp\u003e10.3.2 Tridentate Bis-Urea Catalyzed Fluorination Reactions 345\u003c\/p\u003e \u003cp\u003e10.3.3 Hypervalent Iodine-Catalyzed Fluorination Reactions 347\u003c\/p\u003e \u003cp\u003e10.3.4 \u003ci\u003eN\u003c\/i\u003e-Heterocyclic Carbene-Catalyzed Fluorination Reactions 351\u003c\/p\u003e \u003cp\u003e10.4 DFT Modeling of Enzymatic Fluorination Reaction 354\u003c\/p\u003e \u003cp\u003e10.5 Conclusions 357\u003c\/p\u003e \u003cp\u003eAcknowledgments 357\u003c\/p\u003e \u003cp\u003eReferences 358\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Current Trends in the Design of Fluorine-Containing Agrochemicals \u003c\/b\u003e\u003cb\u003e363\u003cbr\u003e\u003c\/b\u003e\u003ci\u003ePeter Jeschke\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction 363\u003c\/p\u003e \u003cp\u003e11.2 Role of Fluorine in the Design of Modern Agrochemicals 363\u003c\/p\u003e \u003cp\u003e11.3 Fluorinated Modern Agrochemicals 365\u003c\/p\u003e \u003cp\u003e11.3.1 Herbicides Containing Fluorine 366\u003c\/p\u003e \u003cp\u003e11.3.1.1 Acetohydroxyacid Synthase\/Acetolactate Synthase Inhibitors 366\u003c\/p\u003e \u003cp\u003e11.3.1.2 Protoporphyrinogen Oxidase Inhibitors 366\u003c\/p\u003e \u003cp\u003e11.3.1.3 Cellulose Biosynthesis Inhibitors 367\u003c\/p\u003e \u003cp\u003e11.3.1.4 Very Long-Chain Fatty Acid Synthesis Inhibitors 368\u003c\/p\u003e \u003cp\u003e11.3.1.5 Auxin Herbicides 368\u003c\/p\u003e \u003cp\u003e11.3.1.6 Hydroxyphenylpyruvate Dioxygenase Inhibitors 369\u003c\/p\u003e \u003cp\u003e11.3.1.7 Selected Fluorine-Containing Herbicide Development Candidates 370\u003c\/p\u003e \u003cp\u003e11.3.2 Fungicides Containing Fluorine 371\u003c\/p\u003e \u003cp\u003e11.3.2.1 Fungicidal Succinate Dehydrogenase Inhibitors 371\u003c\/p\u003e \u003cp\u003e11.3.2.2 Complex III Inhibitors 373\u003c\/p\u003e \u003cp\u003e11.3.2.3 Sterolbiosynthesis (Sterol-C14-Demethylase) Inhibitors 374\u003c\/p\u003e \u003cp\u003e11.3.2.4 Polyketide Synthase Inhibitors 374\u003c\/p\u003e \u003cp\u003e11.3.2.5 Oxysterol-Binding Protein Inhibitors 376\u003c\/p\u003e \u003cp\u003e11.3.2.6 Selected Fluorine-Containing Fungicide Development Candidates 377\u003c\/p\u003e \u003cp\u003e11.3.3 Insecticides Containing Fluorine 378\u003c\/p\u003e \u003cp\u003e11.3.3.1 Nicotinic Acetylcholine Receptor Competitive Modulators 378\u003c\/p\u003e \u003cp\u003e11.3.3.2 Ryanodine Receptor (RyR) Modulators 382\u003c\/p\u003e \u003cp\u003e11.3.3.3 GABA-Gated CI-Channel Allosteric Modulators 383\u003c\/p\u003e \u003cp\u003e11.3.3.4 Selected Fluorine-Containing Insecticide Development Candidates 385\u003c\/p\u003e \u003cp\u003e11.3.4 Acaricides Containing Fluorine 386\u003c\/p\u003e \u003cp\u003e11.3.4.1 Mitochondrial Complex II Electron Transport Inhibitors 386\u003c\/p\u003e \u003cp\u003e11.3.4.2 Selected Fluorine-Containing Acaricide Development Candidates 387\u003c\/p\u003e \u003cp\u003e11.3.5 Nematicides Containing Fluorine 387\u003c\/p\u003e \u003cp\u003e11.3.5.1 Nematicides with Unknown Biochemical MoA 387\u003c\/p\u003e \u003cp\u003e11.3.5.2 Nematicidal Succinate Dehydrogenase Inhibitors 388\u003c\/p\u003e \u003cp\u003e11.3.5.3 Selected Fluorine-Containing Nematicide Development Candidates 388\u003c\/p\u003e \u003cp\u003e11.4 Summary and Prospects 389\u003c\/p\u003e \u003cp\u003eReferences 390\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12 Precision Radiochemistry for Fluorine-18 Labeling of PET Tracers \u003c\/b\u003e\u003cb\u003e397\u003cbr\u003e\u003c\/b\u003e\u003ci\u003eJian Rong, Ahmed Haider and Steven Liang\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction 397\u003c\/p\u003e \u003cp\u003e12.2 Electrophilic \u003csup\u003e18\u003c\/sup\u003eF-Fluorination with [\u003csup\u003e18\u003c\/sup\u003eF]F\u003csub\u003e2\u003c\/sub\u003e and [\u003csup\u003e18\u003c\/sup\u003eF]F\u003csub\u003e2\u003c\/sub\u003e-Derived Reagents 398\u003c\/p\u003e \u003cp\u003e12.3 Nucleophilic Aliphatic \u003csup\u003e18\u003c\/sup\u003eF-Fluorination 399\u003c\/p\u003e \u003cp\u003e12.3.1 Transition Metal-Free Nucleophilic Aliphatic Substitution with [\u003csup\u003e18\u003c\/sup\u003eF]Fluoride 399\u003c\/p\u003e \u003cp\u003e12.3.2 Transition Metal-Mediated Aliphatic \u003csup\u003e18\u003c\/sup\u003eF-Fluorination 403\u003c\/p\u003e \u003cp\u003e12.4 Nucleophilic Aromatic \u003csup\u003e18\u003c\/sup\u003eF-Fluorination with [\u003csup\u003e18\u003c\/sup\u003eF]Fluoride 405\u003c\/p\u003e \u003cp\u003e12.4.1 Transition Metal-Free Nucleophilic Aromatic \u003csup\u003e18\u003c\/sup\u003eF-Fluorination with [\u003csup\u003e18\u003c\/sup\u003eF]Fluoride 405\u003c\/p\u003e \u003cp\u003e12.4.2 Transition Metal-Mediated Aromatic \u003csup\u003e18\u003c\/sup\u003eF-Fluorination 413\u003c\/p\u003e \u003cp\u003e12.5 \u003csup\u003e18\u003c\/sup\u003eF-Labeling of Multifluoromethyl Motifs with [\u003csup\u003e18\u003c\/sup\u003eF]Fluoride 418\u003c\/p\u003e \u003cp\u003e12.6 Summary and Conclusions 421\u003c\/p\u003e \u003cp\u003eReferences 421\u003c\/p\u003e \u003cp\u003eIndex 427\u003c\/p\u003e","brand":"Wiley-VCH Verlag GmbH","offers":[{"title":"Default Title","offer_id":51742969889111,"sku":"9783527347117","price":999.99,"currency_code":"GBP","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0817\/1739\/5799\/files\/9783527347117.jpg?v=1758387712","url":"https:\/\/bookcurl.com\/products\/organofluorine-chemistry-synthesis-modeling-and-applications-9783527347117","provider":"Book Curl","version":"1.0","type":"link"}