Solvents as reagents in organic synthesis : reactions and applications /: reactions and applications. (2017)

• Record Type: Book
• Further Information: Note: Xiao-Feng Wu.
• Authors: Wu, Xiao-Feng, 1985-
• Editors: Wu, Xiao-Feng
• Contents: List of Contributors xiii 1 The Applications ofWater as Reagents in Organic Synthesis 1; Zhengkai Chen and Hongjun Ren 1.1 Introduction 1 1.2 Incorporation of Hydrogen Atom from theWater 2 1.2.1 1, 2, 3-Triazoles 4 1.3 Incorporation of Oxygen Atom from theWater 7 1.4 Incorporation of Hydroxyl Group fromWater 31 1.5 Traceless Promotion of the Reactions byWater 39 1.6 Conclusions 44 References 44 2 The Applications of Toluene and Xylenes 49; Krishna Nand Singh, Narendra R. Chaubey, and Neetu Singh 2.1 Application of Toluene and Xylenes as Reagents 50 2.2 Oxidation of Methyl Group into Common Functionalities 50 2.3 Application of Methyl Group as Acyl Building Block 51 2.3.1 Synthesis of Carbonyl Compounds 51 2.3.2 Synthesis of Amides 53 2.3.3 Synthesis of N-Aroyl Sulfoximines 54 2.3.4 Synthesis of Esters 55 2.3.5 Synthesis of Thioesters 56 2.4 Application as Alkyl Building Block 60 2.4.1 Synthesis of Nitriles 60 2.4.2 Synthesis of 2-Phenyl Acetic Acid Derivatives 61 2.4.3 Alkylation of Sulfonamides 62 2.4.4 Alkylation ofThiophenols 63 2.4.5 Synthesis of Trifluoromethyl Sulfides 64 2.4.6 Synthesis of Benzyl Esters 64 2.4.7 Synthesis of Phosphate Esters 66 2.4.8 Synthesis of Carbamates, Thioamides, and Esters 66 2.4.9 Synthesis of 3-Benzyl Coumarin Derivatives 66 2.4.10 Decarboxylative Benzylation of Cinnamic Acids 68 2.4.11 Synthesis of Functionalized Oxindoles 68 2.4.12 Synthesis of Dihydroquinolinones 69 2.4.13 Benzylation of Enones 69 2.4.14 Coupling with 1, 3-Dicarbonyl Compounds 70 2.4.15 Benzylation of Pyridine-N-Oxide 70 2.4.16 Synthesis of Dihydrofurans 70 2.4.17 Synthesis of Quinoline Derivatives 71 2.4.18 Reaction with Ethyl Diazoacetate 72 2.4.19 Synthesis of Benzo[b]phosphole Oxides 72 2.4.20 Synthesis of β-Aromatic α-Amino Acid Derivatives 73 2.4.21 Halogenation Reactions 73 2.4.22 N-Benzylation of Isoquinolines 75 2.5 Application as Esters Building Block 76 2.6 Application as Alcohols Building Block 77 References 77 3 The Applications of 1, 4-Dioxane, THF, and Ethers as Versatile Building Blocks in Organic Synthesis 81; Ping Liu, Guanghui Zhang, and Peipei Sun 3.1 Introduction 81 3.2 Cleavage of C(sp3)–H of Ethers 82 3.2.1 Cross-Dehydrogenative Coupling Reactions of Ethers 82 3.2.1.1 C–C Bond Formation 83 3.2.1.2 C–N Bond Formation 91 3.2.1.3 C–O Bond Formation 93 3.2.2 The Formation of C–S Bond 97 3.2.3 Addition of Ethers to C=C and C≡C Bonds 98 3.2.4 Decarboxylative Alkenylation or Alkylation Reactions 104 3.2.5 Radical Alkenylation and Alkynylation of Ethers 106 3.2.6 Radical α-C–H Hydroxyalkylation and Aminoalkylation of Ethers 107 3.2.7 Intermolecular Carbenoid Insertion to α-C–H Bond of Ethers 109 3.2.8 C(sp3)–H Arylation with Arylmetal or Arylboron Reagents 109 3.3 Cleavage of C–O of Ethers 112 3.4 Cleavage of C–C Bonds of Ethers 117 3.5 Conclusion 118 References 118 4 The Application of Dichloromethane and Chloroform as Reagents in Organic Synthesis 125<br /> Anis Tlili and Johannes Schranck 4.1 The Application of Dichloromethane and Chloroform as Reagents in Organic Synthesis 125 4.1.1 Dichloromethane 125 4.1.1.1 Reactions of Dichloromethane with Posttransition Metals 126 4.1.1.2 Reactions of Dichloromethane with Transition Metals 127 4.1.1.3 Reactions of Dichloromethane with Phosphines 135 4.1.1.4 Reactions of Dichloromethane with Amines and Phosphines 136 4.1.1.5 Reactions of Dichloromethane with Amines 136 4.1.1.6 Reactions of Dichloromethane with Amines and Nucleophilic Carbon Derivatives 139 4.1.1.7 Reaction of Dichloromethane with Nucleophilic Sulfur 141 4.1.2 Chloroform 142 4.1.2.1 Reaction of Chloroform with Hydrogen Fluoride 142 4.1.2.2 Reactions of Chloroform with Post-TransitionMetals 142 4.1.2.3 Reactions of Chloroform with Transition Metals 143 4.1.2.4 Formation and Use of Dichlorocarbene 146 References 154 5 The Applications of Acetone and Ethyl Acetates 161; Jie-PingWan 5.1 Acetone 161 5.1.1 Aldol Reaction 161 5.1.2 Claisen–Schmidt Reaction 167 5.1.3 Mannich Reaction 170 5.1.4 Miscellaneous 175 5.2 Ethyl Acetate 182 5.2.1 Transesterification 183 5.2.2 Amidation 187 5.2.3 Miscellaneous 190 References 192 6 N, N-Dimethylformamide and N, N-Dimethylacetamide as Carbon, Hydrogen, Nitrogen, and/or Oxygen Sources 199; Jean Le Bras and Jacques Muzart 6.1 Introduction 199 6.2 Amination 200 6.2.1 Benzylic and (Hetero)aryl Halides 200 6.2.2 Benzyl and Allyl Acetates 205 6.2.3 Ketones and Aldehydes 206 6.2.4 Azoles 207 6.2.5 Others 208 6.3 Amidation andThioamidation 209 6.3.1 Using the DM DimethylamineMoiety 209 6.3.1.1 Aryl and Alkenyl Halides or Triflates 209 6.3.1.2 Acyl Halides 210 6.3.1.3 Carboxylic Acids, α-Ketoacids, Esters, Peresters, and Anhydrides 211 6.3.1.4 Primary Alcohols and Aldehydes 216 6.3.1.5 Methyl Ketones 217 6.3.1.6 Nitriles 218 6.3.1.7 Dibenzyldisulfanes 219 6.3.2 Using the DM DimethylcarbamoylMoiety 219 6.3.2.1 Aryl Halides 219 6.3.2.2 Ketones 221 Compounds 221 6.3.2.4 Phenols 221 6.3.2.5 Thiophenols 223 6.3.2.6 Alkenes 223 6.3.2.7 Alkynes 223 6.3.2.8 Amines 224 6.3.2.9 Amides 225 6.3.2.10 Nitriles 225 6.3.2.11 Isonitriles 226 6.3.2.12 Benzothiazoles 226 6.3.2.13 Selenides and Sulfides 226 6.3.2.14 Aryl-Tethered Activated Alkenes 227 6.3.3 Using the DM Formyl/Acetyl Moiety 227 6.3.4 Using the DMF Dimethylamino-CarbonMoiety 231 6.3.5 Using CH, CHCONMe2, CH2CONMe2, or H(Me)CONMeCH2 Moiety of DM 233 6.3.5.1 Alcohols 233 6.3.5.2 Aldehydes and Ketones 234 6.3.5.3 Carboxylic Acids and α-Ketoacids 235 6.3.5.4 Amines 235 6.3.5.5 Imides and Amides 236 6.3.5.6 Alkenes 237 6.3.5.7 Sulfides 237 6.3.5.8 (Hetero)arenes 238 6.3.5.9 Domino Reactions 240 6.4 Amidination 241 6.4.1 Sulfonamides 241 6.4.2 Enamines 242 6.5 Formylation and Related Domino Reactions 242 6.5.1 Vilsmeier-Mediated Formylations 243 6.5.1.1 (Hetero)arenes 243 6.5.1.2 Alkenes 245 6.5.1.3 O-Silylated Ethers 246 6.5.1.4 Alcohols and Phenols 246 6.5.1.5 Enamines 247 6.5.1.6 Activated Methyl Groups 247 6.5.2 VR-Mediated Domino Reactions 247 6.5.2.1 Formylation and Cyclization 247 6.5.2.2 Haloformylation 249 6.5.2.3 Haloformylation and Cyclization 250 6.5.2.4 Ring Opening, Haloformylation, and Cyclization 252 6.5.2.5 Diformylation 253 6.5.2.6 Intramolecular Formylation-Intermediate Trapping 254 6.5.3 Using Organolithiens or Organomagnesiens 256 6.5.4 Hydroformylation 258 6.5.5 Formoxylation 259 6.6 Carbonylation 260 6.6.1 Carbonyl from DMF 260 6.6.2 Carbon from DM DimethylamineMoiety 262 6.7 Cyanation 264 6.7.1 Carbon from DMF Carbonyl 264 6.7.1.1 Vilsmeier Procedure 264 6.7.1.2 n-BuLi (or Mg)/I2/NH3 Procedure 265 6.7.2 Carbon from DM Dimethyl 266 6.7.2.1 Pd/Cu Procedur
• Edition: 1st
• Publisher Details: Weinheim : Wiley-VCH
• Publication Date: 2017
• Extent: 1 online resource
• Subjects: 541.3482; Solvents; Organic compounds -- Synthesis; Chemical tests and reagents
• Languages: English
• ISBNs: 9783527805631; 9783527805617; 9783527805648
• Related ISBNs: 9783527341962
• Notes: Note: Description based on CIP data; resource not viewed.
• Access Rights: Legal Deposit; Only available on premises controlled by the deposit library and to one user at any one time; The Legal Deposit Libraries (Non-Print Works) Regulations (UK).
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