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9781439824719

Micro Reaction Technology in Organic Synthesis

by ;
  • ISBN13:

    9781439824719

  • ISBN10:

    1439824711

  • Edition: 1st
  • Format: Hardcover
  • Copyright: 2011-03-15
  • Publisher: CRC Press

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Summary

A valuable resource for the modern synthetic chemist, this broadly applicable book addresses the multidisciplinary field of micro reaction technology from novel research technique to a synthetic approach capable of changing the way chemists perform reactions. Concise and informative, it discusses the theory of process-intensification and continuous flow purifications, describes the advantages of miniaturization of organic reactions, and offers expert insight into micro reaction technology and the opportunity to increase the efficiency of organic reactions on a broad scale.

Table of Contents

Prefacep. xiii
Acknowledgmentsp. xv
Authorsp. xvii
Abbreviationsp. xix
Introduction to Micro Reaction Technologyp. 1
What Is Micro Reaction Technology?p. 1
Fabrication/Construction of Micro Reactorsp. 2
Glass Devicesp. 2
Silicon Devicesp. 3
Polymeric Devicesp. 3
Metallic Devicesp. 3
Ceramic Devicesp. 4
Reactor to World Interfacep. 4
Manipulation of Reactants and Products within Flow Reactorsp. 4
Mixing within Micro Reactorsp. 5
Flow Types within Biphasic Systemsp. 6
Advantages of Micro Reaction Technologyp. 7
Process Safetyp. 7
Novel Reaction Conditionsp. 8
Reduced Waste Generationp. 9
On-Site Chemical Processingp. 11
Disadvantages of Micro Reactorsp. 11
Handling of Insoluble Materialsp. 12
Process Intensificationp. 13
In Situ Reaction Monitoringp. 14
Raman Spectroscopyp. 14
In Situ Analysis by FTIR Spectroscopyp. 16
Nuclear Magnetic Resonance Detectionp. 21
Chromatographic Techniquesp. 22
Development of Sensors for Process Monitoringp. 23
Commercial Availability of Continuous Flow Reactor Technologyp. 24
Outlookp. 31
Referencesp. 31
Micro Reactions Employing a Gaseous Componentp. 37
Gas-Phase Micro Reactionsp. 37
Gas-Phase Oxidationsp. 38
Hydrogenation Reactions within Microstructured Reactorsp. 41
Dehydration and Dehydrogenation Reactionsp. 42
Fischer-Tropsch Synthesisp. 43
Synthesis of Methylisocyanate in a Micro Reactorp. 43
Gas-Liquid-Phase Micro Reactionsp. 44
Continuous Flow Chlorination Reactionsp. 44
Continuous Flow Fluorination Reactionsp. 45
Ozonolysis within Micro Reactorsp. 45
Biphasic Carbonylationsp. 48
Transfer Hydrogenations under Continuous Flow Conditionsp. 55
Miscellaneous Biphasic Micro Reactionsp. 57
Gas-Liquid-Solid Micro Reactionsp. 60
Triphasic Oxidations under Flow Conditionsp. 61
Carbonylations Using Solid-Supported Catalystsp. 62
Hydrogenations within Continuous Flow Reactorsp. 63
Slurry-Based Micro Reactionsp. 66
Miscellaneous Triphasic Micro Reactionsp. 69
Referencesp. 70
Liquid-Phase Micro Reactionsp. 77
Nucleophilic Substitutionp. 77
C-C Bond Formation: Acylation Reactionsp. 77
C-C Bond Formation: Alkylation Reactionsp. 78
Enantioselective C-C Bond-Forming Reactionsp. 83
C-O Bond Formation: Esterification Reactionsp. 85
C-O Bond Formation: Etherification Reactionsp. 89
C-O Bond Formation: Epoxide Hydrolysisp. 90
C-N Bond Formation: Alkylation Reactionsp. 90
C-N Bond Formation: Acylation Reactionsp. 93
C-N Bond Formation: Arylation Reactionsp. 98
C-N Bond Formation: Azidation Reactionsp. 99
C-N Bond Formation: Synthesis of Hydroxamic Acidsp. 102
C-N Bond Formation: Aminolysis of Epoxidesp. 103
C-F Bond Formationp. 109
Electrophilic Substitutionp. 113
C-C Bond Formationp. 113
C-N Bond-Forming Reactions: Nitration Reactionsp. 126
C-Hetero Bond-Forming Reactions: Halogenations under Flowp. 130
C-Hetero Bond-Forming Reactions: Diazotizations under Flowp. 133
C-Hetero Bond-Forming Reactions: Sulfonations under Flowp. 136
Nucleophilic Additionp. 136
C-C Bond Formation: Aldol Reaction/Condensationp. 136
C-C Bond Formation: Knoevenagel Condensationp. 139
C-C Bond Formation: Michael Additionp. 142
C-C Bond Formation: Diels-Alder Reactionp. 144
C-C Bond Formation: Horner-Wadsworth-Emmonsp. 146
C-C Bond Formation: Enantioselective Examplesp. 148
C-Hetero Bond Formation: Aza-Michael Additionp. 149
C-Hetero Bond Formation: Alkylation of Aminesp. 151
C-Hetero' Bond Formation: Synthesis of Triazolesp. 152
C-Hetero Bond Formation: Addition of Hydrazine to Carbonyl Compoundsp. 157
Elimination Reactionsp. 158
Dehydration Reactionsp. 158
Dehalogenations: Tris(Trimethylsilyl)Silane-Mediated Reductionsp. 160
Oxidationsp. 163
Oxidations: Inorganic Oxidantsp. 163
Oxidations: Swern-Moffat Oxidationp. 164
Oxidations: TEMPO-Mediated Oxidationsp. 167
Oxidations Using Oxonep. 168
Oxidations: Epoxidations under Flow Conditionsp. 168
Oxidation: Deprotection of Aminesp. 172
Reductionsp. 173
Transition Metal Free Reductionsp. 173
Dibal-H Reductionsp. 173
Metal-Catalyzed Cross-Coupling Reactionsp. 175
Suzuki-Miyaura Reactionp. 175
Heck Reactionp. 177
Sonogashira Reactionp. 183
Other Metal-Catalyzed Coupling Reactionsp. 185
Rearrangementsp. 187
Claisen Rearrangementp. 187
Newman-Kwart Rearrangementp. 191
Hofmann Rearrangementp. 193
Fisher Indolizationp. 195
Curtius Rearrangementp. 196
Dimroth Rearrangementp. 197
Multistep/Multicomponent Liquid-Phase Reactionsp. 198
Multicomponent Synthesis of Heterocyclesp. 198
Multistep Synthesis of 1,2,4-Oxadiazolesp. 199
Continuous Flow Synthesis of Ibuprofenp. 201
Cation-Mediated Sialylation Reactionsp. 203
Oligosaccharide Synthesisp. 205
Synthesis of Indole Alkaloids Using Metal-Coated Capillary Reactorsp. 206
Iododeamination under Flowp. 206
Radical Additions under Flowp. 209
Summaryp. 211
Referencesp. 211
Multi-Phase Micro Reactionsp. 221
Nucleophilic Substitutionp. 221
C-O Bond-Forming Reactions: Esterificationsp. 221
C-N Bond-Forming Reactions: Azidationsp. 224
Electrophilic Substitutionp. 225
Brominationsp. 225
Phosgene Synthesisp. 226
Nucleophilic Additionp. 227
C-C Bond-Forming Reactions: Knoevenagel Condensationp. 227
C-C Bond-Forming Reactions: Michael Additionsp. 229
C-C Bond-Forming Reactions: Henry Reactionp. 230
C-C Bond-Forming Reactions: Diels-Alderp. 232
C-C Bond-Forming Reactions: Benzoin Condensationp. 232
C-C Bond-Forming Reactions: Trifluoromethylation under Continuous Flowp. 234
C-C Bond Formation: Aldol Reactionp. 234
C-N Bond Formation: Cycloaddition Reactionsp. 237
C-O Bond-Forming Reactions: Acetalizationsp. 240
C-S Bond-Forming Reactions: Thioacetalizationsp. 241
Elimination Reactionsp. 241
Dehydration Reactionsp. 241
Dehydration Reactionsp. 242
Oxidation Reactionsp. 242
Catalytic Oxidationsp. 243
Epoxidationsp. 247
Metali¿ Catalyzed Cross-Coupling Reactionsp. 250
Suzuki-Miyaura Reactionp. 250
Heck Coupling Reactionsp. 252
Other Metal-Catalyzed Coupling Reactionsp. 255
Rearrangementsp. 261
Enantioselective Reactionsp. 262
Chemically Promoted Reactionsp. 262
Enzymatic Enantioselective Micro Reactionsp. 266
Multistep/Multicomponent Reactionsp. 272
Independent Multistep Flow Reactionsp. 272
Integrated Multistep Sequencesp. 272
Reagents and Scavengers in Seriesp. 274
Combined Chemical and Biochemical Catalysisp. 274
"Catch and Release" Strategies under Continuous Flowp. 277
Casein Kinase I Inhibitor Synthesisp. 280
Summaryp. 281
Referencesp. 283
Electrochemical and Photochemical Applications of Micro Reaction Technologyp. 289
Electrochemical Synthesis under Continuous Flowp. 289
Electrochemical Oxidationsp. 290
Electrolyte-Free Electroorganic Synthesisp. 296
Electrochemical Reductionsp. 298
Electrolyte-Free Reductions under Flowp. 299
Summaryp. 301
Photochemical Synthesis under Continuous Flowp. 302
Photocycloadditions under Continuous Flowp. 303
Photodecarboxylative Additionp. 307
Photocyanationp. 307
Photochemical Halogenationsp. 308
Nitrite Photolysis under Flow Conditionsp. 309
Photochemical Dimerizationp. 311
Photosensitized Diastereo Differentiationp. 312
Multiphase Photochemical Reactionsp. 312
Photocatalytic Reductionsp. 313
Photocatalytic Oxidation Reactionsp. 314
Photocatalytic Alkylation Reactionsp. 315
Photocatalytic Cyclizationsp. 316
Gas-Liquid Transformationsp. 317
Gas-Liquid-Solid Reactionsp. 321
Summaryp. 321
Referencesp. 321
The Use of Microfluidic Devices for the Preparation and Manipulation of Droplets and Inorganic/Organic Particlesp. 325
Droplet Formation Using Continuous Flow Methodologyp. 325
Polymerization of Droplets under Flowp. 328
Preparation of Inorganic Nanoparticles under Continuous Processing Conditionsp. 330
Formation of Organic Particles within Continuous Flow Devicesp. 332
The Use of Micro Reactors for the Postsynthetic Manipulation of Organic Compoundsp. 336
Mixed Particle Formationp. 338
Microencapsulation of Active Pharmaceuticalsp. 338
Summaryp. 341
Referencesp. 343
Industrial Interest in Micro Reaction Technologyp. 347
MRT in Production Environmentsp. 347
Synthesis of Fine Chemicals Using Micro Reactorsp. 349
Synthesis of Carbamates under Continuous Flow Conditionsp. 350
Production-Scale Synthesis of Ionic Liquidsp. 351
Scalable Technique for the Synthesis of Diarylethenesp. 353
Continuous Flow Synthesis of Light-Emitting Materialsp. 354
2-(2,5-Dimethyl-lH-Pyrrol-l-y1)Ethanol Synthesisp. 356
Synthesis of Pigments under Flow Conditionsp. 357
Production of Thermally Labile Compounds under Flow Conditionsp. 358
Peracetic Acid Production Using an On-Site Microprocessp. 360
The In Situ Synthesis and Use of Diazomethanep. 362
Synthesis of Pharmaceuticals and Natural Products Using Continuous Flow Methodologyp. 363
Ciprofloxacin and Its Analogsp. 363
Synthesis of Pristanep. 363
Synthesis of Imatinib under Flow Conditionsp. 366
Synthesis of Aspirin and Vanisal Sodiump. 368
Synthesis of Suberoylanilide Hydroxamic Acidp. 369
Synthesis of Rimonabant and Efaproxiral Using AlMe3p. 370
Continuous Flow Synthesis of Sildenafilp. 372
Synthesis of 6-Hydroxybuspironep. 372
A Key Step in the Synthesis of (rac)-Trarnadolp. 373
Claisen Rearrangement to Afford 2,2-Dimethyl-2H-1-Benzopyransp. 373
Synthesis of a 5HT1B Antagonistp. 375
Serial Approach to a Novel Anticancer Agent Using Flow Reactorsp. 378
Synthesis of Grossamide under Flow Conditionsp. 378
Synthesis of the Natural Product (±)-Oxomaritidinep. 378
Synthesis of Furofuran Ligansp. 381
Synthesis of Small Doses of Radiopharmaceuticalsp. 382
Summaryp. 384
Referencesp. 384
Microscale Continuous Separations and Purificationsp. 387
Introductionp. 387
Liquid-Liquid Extractionsp. 387
Side-by-Side (Stratified) Contactingp. 388
Three-Phase Microextractionsp. 392
Segmented Flowp. 395
Fluorous Phase Extractionsp. 398
Comparison of Liquid-Liquid Extraction Efficienciesp. 401
Gas-Liquid Separationp. 403
Membrane Separatorsp. 403
Microfiuidic Distillationsp. 403
Solvent Exchange and Solvent Removalp. 407
The Use of Scavenger Resins for Product Purification under Flowp. 410
Trace Metal Removalp. 410
Removal of Unreacted Starting Materialsp. 411
Continuous Flow Resolutionsp. 413
Biocatalytic Resolutionsp. 415
Chemical Racemizationp. 416
Product Isolationp. 418
Antisolvent Precipitationp. 418
Lysozyme Crystallizationp. 420
Solution Crystallizationp. 420
Summaryp. 421
Referencesp. 421
Indexp. 427
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