Abstract
In this Section of the journal, the literature on continuous flow synthesis (primarily organic synthesis and functional materials) from the period of October - December 2016 is presented. All the publications are listed ordered by journal name, with two Review articles appearing at the end. In this quarter the number of papers on continuous flow organic synthesis is relatively less as a few special issues are planned in the coming months. Two contributions on machine learning for optimization in flow synthesis and the scale-up of continuous flow reactors from Eli Lilly are the real highlights of this quarter!
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Organic Synthesis
“Toward the Synthesis of Noroxymorphone via Aerobic Palladium-Catalyzed Continuous Flow N-Demethylation Strategies” Gutmann, B.; Elsner, P.; Cox, D. P.; Weigl, U.; Roberge, D. M.; Kappe, C. O. ACS Sustainable Chemistry & Engineering 2016, 4, 6048–6061
“Selective Direct Synthesis of Trialkoxysilanes in a Packed Bed Flow Tubular Reactor” Chigondo, F.; Zeelie, B.; Watts, P. ACS Sustainable Chemistry & Engineering 2016, 4, 6237–6243
“Countercurrent Droplet-Flow-Based Mini Extraction with Pulsed Feeding and without Moving Parts” Xu, C.; Jing, S.; Chu, Y. AIChE Journal 2016, 62, 3685–3698
“Continuous Consecutive Reactions with Inter-Reaction Solvent Exchange by Membrane Separation” Peeva, L.; Da Silva Burgal, J.; Heckenast, Z.; Brazy, F.; Cazenave, F.; Livingston, A. Angewandte Chemie 2016, 128, 13774–13777
“Development of a Continuous Process for a-Thio-β-Chloroacrylamide Synthesis with Enhanced Control of a Cascade Transformation” Dennehy, O. C.; Cacheux, V. M.; Deadman, B. J.; et al. Beilstein Journal of Organic Chemistry 2016, 12, 2511–2522
“Continuous-Flow Synthesis of Primary Amines: Metal-Free Reduction of Aliphatic and Aromatic Nitro Derivatives with Trichlorosilane” Porta, R.; Puglisi, A.; Colombo, G.; Rossi, S.; Benaglia, M. Beilstein Journal of Organic Chemistry 2016, 12, 2614–2619
“Towards the Development of Continuous, Organocatalytic, and Stereoselective Reactions in Deep Eutectic Solvents” Brenna, D.; Massolo, E.; Puglisi, A.; et al. Beilstein Journal of Organic Chemistry 2016, 12, 2620–2626
“Let the Substrate Flow, not the Enzyme: Practical Immobilization of D-Amino Acid Oxidase in a Glass Microreactor for Effective Biocatalytic Conversions” Bolivar, J. M.; Tribulato, M. A.; Petrasek, Z.; Nidetzky, B. Biotechnology and Bioengineering 2016, 113, 2342–2349
“Continuous Precipitation of Process Related Impurities from Clarified Cell Culture Supernatant Using a Novel Coiled Flow Inversion Reactor (CFIR)” Kateja, N.; Agarwal, H.; Saraswat, A.; Bhat, M.; Rathore, A. S. Biotechnology Journal 2016, 11, 1320–1331
“Review: Microstructured Reactors as Efficient Tool for the Operation of Selective Oxidation Reactions” Pennemann, H.; Kolb, G. Catalysis Today 2016, 278, 3–21
“Selectivity and Lifetime Effects in Zeolite-Catalysed Baeyer-Villiger Oxidation Investigated in Batch and Continuous Flow” Yakabi, K.; Milne, K.; Buchard, A.; Hammond, C. ChemCatChem 2016, 8, 3490–3498
“Gas-Liquid Mass Transfer in a Falling Film Microreactor: Effect of Reactor Orientation on Liquid-Side Mass Transfer Coefficient” Lokhat, D.; Domah, A. K.; Padayachee, K.; Baboolal, A.; Ramjugernath, D. Chemical Engineering Science 2016, 155, 38–44
“The Plug & Play Reactor: A Highly Flexible Device for Heterogeneous Reactions in Continuous Flow” Lichtenegger, G. J.; Tursic, V.; Kitzler, H.; Obermaier, K.; Khinast, J. G.; Gruber-Wölfler, H. Chemie Ingenieur Technik 2016, 88, 1518–1523
“Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process” Teci, M.; Tilley, M.; McGuire, M. A.; Organ, M. G. Chemistry-A European Journal 2016, 22, 17407–17415
“Design of a Heterogeneous Catalytic Process for the Continuous and Direct Synthesis of Lactide from Lactic Acid” Upare, P. P.; Yoon, J. W.; Hwang, D. W.; et al. Green Chemistry 2016, 18, 5978–5983
“A Combination of Natural Deep Eutectic Solvents and Microflow Technology: A Sustainable Innovation for the Tandem Synthesis of 3-Aminohexahydrocoumarins” Zamani, P.; Khosropour, A. R. Green Chemistry 2016, 18, 6450–6455
“Reduction of Catalyst Deactivation Effects on Styrene Monomer Production in Multistage Radial Fixed Bed Reactor” Bahadori, F.; Azizi, A.; Ghasemzadeh, K. Journal of Flow Chemistry 2016, 6, 315–322
“In Situ Generation and Diels—Alder Reaction of Benzynes Derivatives with 5-Membered Ring Heterocycles Using a Microcapillary Flow Reactor” Khadra, A.; Organ, M. G. Journal of Flow Chemistry 2016, 6, 293–296
“Application of Flow Chemistry to Macrocyclization of Crown Ethers” Fodi, T.; Kupai, J.; Túrós, G.; et al. Journal of Flow Chemistry 2016, 6, 297–301
“Microfluidic Implementation of Ru-Catalyzed Methylation of Amines Using CO2 as Carbon Source” Perkins, G.; Khatib, O.; Peterson, M.; et al. Journal of Flow Chemistry 2016, 6, 302–308
“Kinetic Study and Intensification of Acetyl Guaiacol Nitration with Nitric Acid—Acetic Acid System in a Microreactor” Zhang, C.; Zhang, J.; Luo, G. Journal of Flow Chemistry 2016, 6, 309–314
“Dispersion Photopolymerization of Acrylated Oligomers Using a Flexible Continuous Reactor” Roose, P.; Berlier, M.; Lazzaroni, R.; Leclère, P. Macromolecular Reaction Engineering 2016, 10, 502–509
“A Single-Stage, Continuous High-Efficiency Extraction Device (HEED) for Flow Synthesis” Day, C.; Saldarriaga, A.; Tilley, M.; Hunter, H.; Organ, M. G.; Wilson, D. J. Organic Process Research & Development 2016, 20, 1738–1743
“A Small-Footprint, High-Capacity Flow Reactor for UV Photochemical Synthesis on the Kilogram Scale” Elliott, L. D.; Berry, M.; Harji, B.; Klauber, D.; Leonard, J.; Booker-Milburn, K. I. Organic Process Research & Development 2016, 20, 1806–1811
“Development and Manufacturing GMP Scale-up of a Continuous Ir-Catalyzed Homogeneous Reductive Amination Reaction” May, S. A.; Johnson, M. D.; Buser, J. Y.; et al. Organic Process Research & Development 2016, 20, 1870–1898
“Life Cyle Assessment Based Environmental Performance Comparison of Batch and Continuous Processing: A Case of 4-D-Erythronolactone Synthesis” Lee, C. K.; Khoo, H. H.; Tan, R. B. Organic Process Research & Development 2016, 20, 1937–1948
“Handling Hazards Using Continuous Flow Chemistry: Synthesis of N 1-Aryl-[1, 2, 3]-Triazoles from Anilines via Telescoped Three-Step Diazotization, Azidodediazotization, and [3+2] Dipolar Cycloaddition Processes” Teci, M.; Tilley, M.; McGuire, M. A.; Organ, M. G. Organic Process Research & Development 2016, 20, 1967–1973
“Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm” Cortés-Borda, D.; Kutonova, K. V.; Jamet, C.; Trusova, M. E.; Zammattio, F.; Truchet, C.; Rodriguez-Zubiri, M.; Felpin, F. X. Organic Process Research & Development 2016, 20, 1979–1987
“Using Flow to Outpace Fast Proton Transfer in an Organometallic Reaction for the Manufacture of Verubecestat (MK-8931)” Thaisrivongs, D. A.; Naber, J. R.; McMullen, J. P. Organic Process Research & Development 2016, 20, 1997–2004
“Microwave Heated Continuous Flow Palladium (II)-Catalyzed Desulfitative Synthesis of Aryl Ketones” Skillinghaug, B.; Rydfjord, J.; Savmarker, J.; Larhed, M. Organic Process Research & Development 2016, 20, 2005–2011
“A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow” Zhao, Y.; King, G.; Kwan, M. H.; Blacker, A. J. Organic Process Research & Development 2016, 20, 2012–2018
“Continuous-Flow Diazotization for Efficient Synthesis of Methyl 2-(Chlorosulfonyl) Benzoate: An Example of Inhibiting Parallel Side Reactions” Yu, Z.; Dong, H.; Xie, X.; Liu, J.; Su, W. Organic Process Research & Development 2016, 20, 2116–2123
“Microfluidic Synthesis of Size-Controlled and Morphologically Homogeneous Lead Trinitroresorcinate Produced by Segmented Flow” Zhou, N.; Zhu, P.; Rong, Y.; et al. Propellants, Explosives, Pyrotechnics 2016, 41, 899–905
“A Laboratory-Scale Continuous Flow Chlorine Generator for Organic Synthesis” Strauss, F. J.; Cantillo, D.; Guerra, J.; Kappe, C. O. Reaction Chemistry & Engineering 2016, 1, 472–476
“Decay Kinetics of Sensitive Bioinorganic Species in a SuperFocus Mixer at Ambient Conditions” Schurr, D.; Strassl, F.; Liebhäuser, P.; Rinke, G.; Dittmeyer, R.; Herres-Pawlis, S. Reaction Chemistry & Engineering 2016, 1, 485–493
“A Miniature CSTR Cascade for Continuous Flow of Reactions Containing Solids” Mo, Y.; Jensen, K. F. Reaction Chemistry & Engineering 2016, 1, 501–507
“Combining Microfluidics and FT-IR Spectroscopy: Towards Spatially Resolved Information on Chemical Processes” Perro, A.; Lebourdon, G.; Henry, S.; Lecomte, S.; Servant, L.; Marre, S. Reaction Chemistry & Engineering 2016, 1, 577–594
“A Greener Process for Flow C-H Chlorination of Cyclic Alkanes Using in Situ Generation and on-Site Consumption of Chlorine Gas” Fukuyama, T.; Tokizane, M.; Matsui, A.; Ryu, I. Reaction Chemistry & Engineering 2016, 1, 613–615
“Photonic Contacting of Gas-Liquid Phases in a Falling Film Microreactor for Continuous-Flow Photochemical Catalysis with Visible Light” Rehm, T. H.; Gros, S.; Löb, P.; Renken, A. Reaction Chemistry & Engineering 2016, 1, 636–648
“Continuous Flow Gas Phase Photoreforming of Methanol at Elevated Reaction Temperatures Sensitised by Pt/TiO2” Caravaca, A.; Daly, H.; Smith, M.; Mills, A.; Chansai, S.; Hardacre, C. Reaction Chemistry & Engineering 2016, 1, 649–657
“Suzuki-Miyaura Cross-Coupling Optimization Enabled by Automated Feedback” Reizman, B. J.; Wang, Y.-M.; Buchwald, S. L.; Jensen, K. F. Reaction Chemistry & Engineering 2016, 1, 658–666
“Direct Amide Synthesis over Core-Shell TiO2@ NiFe2O4 Catalysts in a Continuous Flow Radiofrequency-Heated Reactor” Liu, Y.; Gao, P.; Cherkasov, N.; Rebrov, E. V. RSC Advances 2016, 6, 100997–101007
“A Benchtop NMR Spectrometer as a Tool for Monitoring Mesoscale Continuous-Flow Organic Synthesis: Equipment Interface and Assessment in Four Organic Transformations” Archambault, C. M.; Leadbeater, N. E. RSC Advances 2016, 6, 101171–101177
“The Continuous-Flow Synthesis of Carbazate Hydrazones Using a Simplified Computer-Vision Controlled Liquid-Liquid Extraction System” O’Brien, M.; Cooper, D. A.; Mhembere, P. Tetrahedron Letters 2016, 57, 5188–5191
“Isopropyl 2-Ethoxyacetate—An Efficient Acylating Agent for Lipase-Catalyzed Kinetic Resolution of Amines in Batch and Continuous-Flow Modes” Oláh, M.; Boros, Z.; Hornyánszky, G.; Poppe, L. Tetrahedron 2016, 72, 7249–7255
“Applying Green Processes and Techniques to Simplify Reaction Work-ups” Andrade, C. K. Z.; Dar, A. R. Tetrahedron 2016, 72, 7375–7391
“Continuous-Flow Electrophilic Amination of Arenes and Schmidt Reaction of Carboxylic Acids Utilizing the Superacidic Trimethylsilyl Azide/Triflic Acid Reagent System” Chen, Y.; Gutmann, B.; Kappe, C. O. The Journal of Organic Chemistry 2016, 81, 9372–9380
“Synthesis of a-Nitro Carbonyls via Nitrations in Flow” Chentsova, A.; Ushakov, D. B.; Seeberger, P. H.; Gilmore, K. The Journal of Organic Chemistry 2016, 81, 9415–9421
“Selective Pinacol-Coupling Reaction Using a Continuous Flow System” Sotto, N.; Cazorla, C.; Villette, C.; Billamboz, M.; Len, C. The Journal of Organic Chemistry 2016, 81, 11065–11071
“Application of the Photoredox Coupling of Trifluoroborates and Aryl Bromides to Analog Generation Using Continuous Flow” DeLano, T. J.; Bandarage, U. K.; Palaychuk, N.; Green, J.; Boyd, M. J. The Journal of Organic Chemistry 2016, 81, 12525–12531
Nanomaterials
“Bifunctional Ruthenium Nanoparticle-SILP Catalysts (RuNPs@ SILP) for the Hydrodeoxygenation of Eucalyptol under Batch and Continuous Flow Conditions” Luska, K. L.; Migowski, P.; El Sayed, S.; Leitner, W. ACS Sustainable Chemistry & Engineering 2016, 4, 6186–6192
“Controllable Synthesis of Gold Nanoparticles in Aqueous Solution by Microwave Assisted Flow Chemistry” Bayazit, M. K.; Yue, J.; Cao, E.; Gavriilidis, A.; Tang, J. ACS Sustainable Chemistry & Engineering 2016, 4, 6435–6442
“Continuous Formation of a Seed Layer and Vertical ZnO Nanowire Arrays Enabled by Tailored Reaction Kinetics in a Microreactor” Choi, C.-H.; Levin, J. B.; Chang, C.-h. CrystEngComm 2016, 18, 8645–8652
“A Spray-Drying Continuous-Flow Method for Simultaneous Synthesis and Shaping of Microspherical High Nuclearity MOF Beads” Garzón-Tovar, L.; Cano-Sarabia, M.; Carné-Sánchez, A.; Carbonell, C.; Imaz, I.; Maspoch, D. Reaction Chemistry & Engineering 2016, 1, 533–539
Reviews
“Aerobic Oxidations in Flow: Opportunities for the Fine Chemicals and Pharmaceuticals Industries” Gavriilidis, A.; Constantinou, A.; Hellgardt, K.; et al. Reaction Chemistry & Engineering 2016, 1, 595–612
“Engineering Chemistry: Integrating Batch and Flow Reactions on a Single, Automated Reactor Platform” Fitzpatrick, D; Ley, S. Reaction Chemistry & Engineering 2016, 1, 629–635
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Kulkarni, A.A. Highlights from the Flow Chemistry Literature 2016 (Part 4). J Flow Chem 7, 23–27 (2017). https://doi.org/10.1556/1846.2017.11111
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DOI: https://doi.org/10.1556/1846.2017.11111