Details
Green Solvents in Organic Synthesis
1. Aufl.
142,99 € |
|
Verlag: | Wiley-VCH (D) |
Format: | EPUB |
Veröffentl.: | 07.03.2024 |
ISBN/EAN: | 9783527841936 |
Sprache: | englisch |
Anzahl Seiten: | 464 |
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Beschreibungen
<b>Green Solvents in Organic Synthesis</b> <p> <b>Essential reference on replacing conventional solvents with greener alternatives in industrial chemicals synthesis and production</b> <p>A well-timed book promoting sustainability in synthesis and production of chemicals, <i>Green Solvents in Organic Synthesis </i>details various green solvents, solvent systems, and solubilization techniques, including their chemistry, physiochemical properties, performance, and distinct applications, presenting a greener approach to conventional solvents by replacing them with sustainable alternatives that have similarities in their reaction mechanisms. <p>Edited by four highly qualified academics with significant research experience in the field, <i>Green Solvents in Organic Synthesis </i>includes information on: <ul><li>Water and liquid polymers (Polyethylene glycol PEG), Acetonitrile, DMSO, Dimethyl carbonate, Ionic liquids, and Supercritical fluids)</li><li>Bio-based solvents (Cyrene, γ-Valerolactone (GVL), Lactic acid, 2-MeTHF) and deep eutectic solvents (DESs)</li><li>Alcohols (MeOH, EtOH, i-PrOH, n-BuOH, t-BuOH, Ethylene glycol), ketones (Acetones, MEK, MIBK, Cyclohexanone), and esters (Methyl acetate, Ethyl acetate, i-PrOAc, n-BuOAc)</li><li>Technical, economic, and environmental aspects of green solvents and how to maximize their reuse and recycling to alleviate pollution and reduce energy consumption</li></ul> <p>For chemists in a variety of disciplines, <i>Green Solvents in Organic Synthesis </i>is an essential reference that provides foundational knowledge of green solvents, along with key features of each class of green solvent within the context of organic reactions for industrial and laboratory synthesis.
<p><b>1 Recent Achievements in Organic Reactions in Alcohols 1<br /> </b><i>Lan Zhao, Man Zhao, Meng-Ge Wei, Hong-Ru Li, and Liang-Nian He</i></p> <p>1.1 Introduction 1</p> <p>1.2 Alcohols as Green Solvents 6</p> <p>1.2.1 Hydrogenation/Reduction Reaction 6</p> <p>1.2.2 Oxidation Reaction 8</p> <p>1.2.3 Substitution Reaction 10</p> <p>1.2.4 Addition Reaction 11</p> <p>1.2.5 Cyclization Reaction 13</p> <p>1.2.6 Coupling Reaction 18</p> <p>1.2.7 Condensation/Ring Condensation Reaction 21</p> <p>1.3 Alcohols as Green Solvents and Catalysts 28</p> <p>1.3.1 Addition Reaction 28</p> <p>1.3.2 Cyclization Reaction 28</p> <p>1.3.3 Coupling Reaction 30</p> <p>1.3.4 Condensation Reaction 30</p> <p>1.3.5 Metathesis Reaction 35</p> <p>1.4 Alcohols as Green Solvents and Hydrogen Donors 35</p> <p>1.5 Miscellaneous 39</p> <p>1.5.1 Polyethylene Glycol as a Solvent for CO 2 Capture and Conversion 39</p> <p>1.5.2 Polyethylene Glycol Radical-Initiated Oxidation Reactions in Compressed Carbon Dioxide 41</p> <p>1.5.3 Ring-Opening Reaction 43</p> <p>1.6 Summary and Concluding Remarks 45</p> <p>Acknowledgments 46</p> <p>References 46</p> <p><b>2 Recent Achievements in Organic Reactions in MeCN 51<br /> </b><i>Tongtong Xing, Guizhi Zhai, Linna Wu, Xiaofen Wang, and Zechao Wang</i></p> <p>2.1 Introduction 51</p> <p>2.2 MeCN in Transition Metal-catalyzed Reactions Without Radicals Involved 52</p> <p>2.2.1 Transition Metal-catalyzed Addition Reactions in MeCN 52</p> <p>2.2.2 Transition Metal-catalyzed Oxidation Reactions in MeCN 56</p> <p>2.2.3 Transition Metal-catalyzed Reduction Reactions in MeCN 64</p> <p>2.2.4 Transition Metal-catalyzed Substitution Reactions in MeCN 66</p> <p>2.2.5 Transition Metal-catalyzed Cyclization Reactions in MeCN 74</p> <p>2.3 MeCN in Transition Metal-free Catalyzed Reactions Without Radicals Involved 80</p> <p>2.3.1 Transition Metal-free Catalyzed Cyclization Reactions in MeCN 80</p> <p>2.3.2 Transition Metal-free Catalyzed Multicomponent Reactions in MeCN 84</p> <p>2.3.3 Transition Metal-free Catalyzed C—X Bond Formation in MeCN 87</p> <p>2.4 MeCN in C—X Bonds Formation With Radicals Involved 90</p> <p>2.4.1 C—C, C—Si Bond Formation in MeCN 90</p> <p>2.4.2 C—N, C—P Bond Formation in MeCN 93</p> <p>2.4.3 C—O, C—S Bond Formation in MeCN 96</p> <p>2.4.4 C-Halogen Bond Formation in MeCN 98</p> <p>2.5 Conclusion 102</p> <p>References 102</p> <p><b>3 Recent Achievements in Organic Reactions in Bio-based Solvents 107<br /> </b><i>Shaomin Chen, Noman Haider Tariq, and Yanlong Gu</i></p> <p>3.1 Introduction 107</p> <p>3.2 Glycerol 108</p> <p>3.3 Polyethylene Glycols (PEGs) 112</p> <p>3.4 2-Methyltetrahydrofuran (2-MeTHF) 114</p> <p>3.5 Cyclopentyl Methyl Ether (CPME) 117</p> <p>3.6 Organic Carbonates 120</p> <p>3.7 γ-Valerolactone (GVL) 125</p> <p>3.8 Ethyl Lactate (EL) 128</p> <p>3.9 Miscellaneous 130</p> <p>3.10 Conclusions and Outlook 131</p> <p>References 131</p> <p><b>4 Recent Achievements in Organic Reactions in DMSO 137<br /> </b><i>Peng Yuan, Jia-Chen Xiang, and An-Xin Wu</i></p> <p>4.1 Pummerer-type Activation of DMSO 138</p> <p>4.2 Selectfluor-enabled Activation of DMSO 148</p> <p>4.3 Activation of DMSO Enabled by Single-electron Transformation 151</p> <p>4.4 Electrocatalytic Synthesis Enabled Activation of DMSO 163</p> <p>4.5 Photocatalytic Reaction Enabled Activation of DMSO 164</p> <p>4.6 DMSO Acts as the Metal Ligand 171</p> <p>4.7 Some Special Activation or Usage of DMSO 174</p> <p>4.8 Summary and Outlook 181</p> <p>References 181</p> <p><b>5 The Use of DMC as Green Solvent in Organic Synthesis 185<br /> </b><i>Xinxin Qi and Xiao-Feng Wu</i></p> <p>5.1 Introduction 185</p> <p>5.2 Organic Reactions in DMC 185</p> <p>References 197</p> <p><b>6 Applications of Green Deep Eutectic Solvents (DESs) in Synthetic Transformations 199<br /> </b><i>Zhuan Zhang and Taoyuan Liang</i></p> <p>6.1 Introduction 199</p> <p>6.2 Cross-coupling Reactions in Deep Eutectic Solvents 201</p> <p>6.2.1 C—C Bond Couplings 201</p> <p>6.2.2 C—N Bond Couplings 210</p> <p>6.2.3 C—O Bond Couplings 211</p> <p>6.2.4 C—S Bond Couplings 212</p> <p>6.3 Oxidation Reactions in Deep Eutectic Solvents 213</p> <p>6.3.1 Metal-catalyzed Oxidation 213</p> <p>6.3.2 Other Oxidative Processes 214</p> <p>6.4 Reduction Reactions in Deep Eutectic Solvents 217</p> <p>6.4.1 Metal-catalyzed Reduction 217</p> <p>6.4.2 Other Catalytic Reduction 218</p> <p>6.5 Cyclization Reactions in Deep Eutectic Solvents 219</p> <p>6.5.1 Synthesis of Five-membered Ring 219</p> <p>6.5.2 Synthesis of Six-membered Ring 220</p> <p>6.6 Condensation Reactions in Deep Eutectic Solvents 221</p> <p>6.6.1 DES as the Catalyst/Solvent System for Condensation 221</p> <p>6.6.2 Other Catalytic System for Condensation 223</p> <p>6.7 Multicomponent Reactions in Deep Eutectic Solvents 224</p> <p>6.7.1 One-pot Three-component Reaction 224</p> <p>6.7.2 One-pot Four-component Reaction 227</p> <p>6.8 Other Organic Reactions in Deep Eutectic Solvents 228</p> <p>6.8.1 Isomerization Reaction 228</p> <p>6.8.2 Ring-opening Reaction 230</p> <p>6.8.3 Esterification Reaction 230</p> <p>6.9 Polymerization in DSEs 231</p> <p>6.9.1 Anionic Polymerization of Alkenes 231</p> <p>6.9.2 Glycolysis and Polyesterification 231</p> <p>6.9.3 Oxidative Polymerization 232</p> <p>6.9.4 Visible-light-driven RAFT Polymerization 232</p> <p>6.10 Conclusion 233</p> <p>References 233</p> <p><b>7 Recent Achievements in Organic Reactions in Ionic Liquids 237<br /> </b><i>Jianxiao Li and Huanfeng Jiang</i></p> <p>7.1 Introduction 237</p> <p>7.2 Transition Metal-catalyzed Reactions 238</p> <p>7.2.1 Palladium-catalyzed Cascade Cyclization Reaction 239</p> <p>7.2.2 Carbonylation Reactions 248</p> <p>7.2.3 Sonogashira Coupling Reactions 252</p> <p>7.2.4 Suzuki Coupling Reactions 255</p> <p>7.2.5 Copper-catalyzed Coupling Reactions 257</p> <p>7.3 Outlook 259</p> <p>List of Abbreviations 259</p> <p>References 260</p> <p><b>8 Recent Achievements in Organic Reactions in Ketones and Esters 263<br /> </b><i>Fan-Lin Zeng and Bing Yu</i></p> <p>8.1 Introduction 263</p> <p>8.2 Organic Reactions in Ketones 263</p> <p>8.2.1 Organic Reactions in Cyrene 263</p> <p>8.2.2 Organic Reactions in NBP 266</p> <p>8.3 Organic Reactions in Esters 268</p> <p>8.3.1 Organic Reactions in Organic Carbonates 268</p> <p>8.3.2 Organic Reactions in γ-Valerolactone 270</p> <p>8.3.3 Organic Reactions in Ethyl Lactate 273</p> <p>8.4 Conclusion 275</p> <p>References 275</p> <p><b>9 Recent Achievements in Organic Reactions in Polyethylene Glycol 279<br /> </b><i>Zhiping Yin</i></p> <p>9.1 Introduction 279</p> <p>9.2 PEG in Pd-catalyzed Coupling Reactions 280</p> <p>9.2.1 Pd-catalyzed C—C, C—Si Bonds Formation in PEG 280</p> <p>9.2.2 Pd-catalyzed C—N, C—P Bond Formation in PEG 290</p> <p>9.2.3 Pd-catalyzed C—O Bond Formation in PEG 291</p> <p>9.2.4 Pd-catalyzed C—B Bond Formation in PEG 291</p> <p>9.3 PEG in Cu-catalyzed Reactions 292</p> <p>9.3.1 Cu-catalyzed C—C Bond Formation in PEG 292</p> <p>9.3.2 Cu-catalyzed C—N Bond Formation in PEG 293</p> <p>9.3.3 Cu-catalyzed C—O, C—S, and C—Se Bond Formation in PEG 296</p> <p>9.4 PEG in Ni, Ru, and Pt-catalyzed Reactions 299</p> <p>9.5 PEG in Organocatalysis Reactions 302</p> <p>9.6 PEG in Multicomponent Reactions 304</p> <p>9.7 PEG in Cyclization Reactions 306</p> <p>9.7.1 Synthesis of Five-membered Ring Systems 306</p> <p>9.7.2 Synthesis of Six and Seven-membered Ring Systems 308</p> <p>9.8 Conclusion 309</p> <p>Acknowledgments 310</p> <p>References 310</p> <p><b>10 Recent Advances in Organic Reactions Using Water as Solvent 317<br /> </b><i>Chang-Sheng Wang, Qiao Sun, Guowei Wang, Wei He, Zheng Fang, and Kai Guo</i></p> <p>10.1 Introduction 317</p> <p>10.2 Cross-Coupling Reactions 318</p> <p>10.2.1 C–C Cross-Coupling 318</p> <p>10.2.2 C–N Cross-Coupling 336</p> <p>10.2.3 C–S Cross-Coupling 342</p> <p>10.2.4 C–P Cross-Coupling 346</p> <p>10.3 C–H Functionalization 347</p> <p>10.3.1 C–C Bond Formation 347</p> <p>10.3.2 C–N Bond Formation 364</p> <p>10.3.3 C–O Bond Formation 367</p> <p>10.3.4 C–X Bond Formation 369</p> <p>10.3.5 C–H Annulation/Cyclization 370</p> <p>10.4 C–C Activation 374</p> <p>10.5 C–O Cleavage Reactions 376</p> <p>10.6 Oxidative and Reductive Reactions 377</p> <p>10.6.1 Electrochemical Oxidation 377</p> <p>10.6.2 Reduction and Related Reactions 379</p> <p>10.7 Substitution Reactions 381</p> <p>10.7.1 Nucleophilic Substitution 381</p> <p>10.7.2 Electrophilic Substitution 383</p> <p>10.7.3 Radical Substitution 384</p> <p>10.8 Addition Reactions 386</p> <p>10.8.1 Nucleophilic Addition 386</p> <p>10.8.2 Alkene/Alkyne Functionalization via Radical Addition 392</p> <p>10.8.3 Alkene or Alkyne Functionalization via Radical-Free Addition 396</p> <p>10.8.4 Cycloaddition Reactions 399</p> <p>10.9 Cyclization or Annulation Reactions 403</p> <p>10.9.1 Radical-Free Cyclization/Annulation 403</p> <p>10.9.2 Radical Cyclization 406</p> <p>10.10 Multicomponent Reaction (MCR) 410</p> <p>10.11 Domino/Tandem/Cascade Reactions 417</p> <p>10.11.1 Chemo-Domino/Tandem/Cascade Reactions 417</p> <p>10.11.2 Chemoenzymatic Reactions 422</p> <p>10.12 Rearrangement or Insertion Reactions 425</p> <p>10.12.1 Rearrangement Reactions 425</p> <p>10.12.2 Carbene Insertion/Transfer Reactions 429</p> <p>10.13 Amide Condensation Reactions 431</p> <p>10.14 Summary and Conclusions 435</p> <p>Acknowledgments 435</p> <p>References 435</p> <p>Index 443</p>
<p><b>Xiao-Feng Wu, PhD, </b>is a Professor at Dalian Institute of Chemical Physics, CAS.</p> <p><b>Zhiping Yin, PhD, </b>is a Professor at the School of Pharmacy of Jiangsu University.</p> <p><b>Liang-Nian He, PhD, </b>is a Professor at Nankai University.</p> <p><b>Feng Wang, PhD, </b>serves as the vice director of Dalian Institute of Chemical Physics, CAS and the director of the Biomass-Conversion and Bio-Energy division at the Bioenergy Chemical Group.</p>
<p> <b>Essential reference on replacing conventional solvents with greener alternatives in industrial chemicals synthesis and production</b> <p>A well-timed book promoting sustainability in synthesis and production of chemicals, <i>Green Solvents in Organic Synthesis </i>details various green solvents, solvent systems, and solubilization techniques, including their chemistry, physiochemical properties, performance, and distinct applications, presenting a greener approach to conventional solvents by replacing them with sustainable alternatives that have similarities in their reaction mechanisms. <p>Edited by four highly qualified academics with significant research experience in the field, <i>Green Solvents in Organic Synthesis </i>includes information on: <ul><li>Water and liquid polymers (Polyethylene glycol PEG), Acetonitrile, DMSO, Dimethyl carbonate, Ionic liquids, and Supercritical fluids)</li><li>Bio-based solvents (Cyrene, γ-Valerolactone (GVL), Lactic acid, 2-MeTHF) and deep eutectic solvents (DESs)</li><li>Alcohols (MeOH, EtOH, i-PrOH, n-BuOH, t-BuOH, Ethylene glycol), ketones (Acetones, MEK, MIBK, Cyclohexanone), and esters (Methyl acetate, Ethyl acetate, i-PrOAc, n-BuOAc)</li><li>Technical, economic, and environmental aspects of green solvents and how to maximize their reuse and recycling to alleviate pollution and reduce energy consumption</li></ul> <p>For chemists in a variety of disciplines, <i>Green Solvents in Organic Synthesis </i>is an essential reference that provides foundational knowledge of green solvents, along with key features of each class of green solvent within the context of organic reactions for industrial and laboratory synthesis.