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核心——微反应器的设计各式各样 [14] ,如何匹配相 using selectfluor[J]. Journal of the American Chemical Society, 1997,
关的设备和工艺条件,令氟化反应得以优化,也是 119(49): 11743-11746.
[20] Marcus Baumann, Ian R Baxendale, Steven V Ley. The use of
目前迫在眉睫的问题。微反应技术的出现定会使传 diethylaminosulfur trifluoride (dast) for fluorination in a continuous-
统氟化工艺受到巨大冲击,而微反应技术的应用也 flow microreactor[J]. Synlett, 2008,(14): 2111-2114.
[21] Natshumi Wakita, Shoji Hara. Polyfluoroalkylation of carbonyl
势必将氟化反应推向更为高效、安全、环保、可控 compounds by polyfluoroalkyl anions generated from
以及连续化的方向蓬勃发展。 polyfluorocarboxamides[J]. Heterocycles, 2014, 88(2): 1201-1212.
[22] Shimizu M, Hiyama T. Modern synthetic methods for fluorine-
参考文献: substituted target molecules[J]. Angewandte Chemie International
Edition, 2004, 44(2): 214-231.
[1] Kenneth L Kirk. Selective fluorination in drug design and development: [23] Boris I Usachev. Chemistry of fluoroalkyl-substituted 1,2,3-triazoles[J].
An overview of biochemical rationales[J]. Current Topics in Medicinal Journal of Fluorine Chemistry, 2018, 210: 6-45.
Chemistry, 2006, 6(14): 1447-1456. [24] Thomas H Rehm. Photochemical fluorination reactions-a promising
[2] Karolin Geyer, Tomas Gustafsson, Peter H Seeberger. Developing research field for continuousflow synthesis[J]. Chemical Engineering
continuous-flow microreactors as tools for synthetic chemists[J]. Technology, 2015, 39(1): 66-80.
Synlett, 2009, 15: 2382-2391. [25] Devender S Negi, Lars Köppling, Kai Lovis, et al. Kinetics and
[3] Kenneth L Kirk. Fluorination in medicinal chemistry: Methods, process development for deoxofluorination of a steroid[J]. Organic
strategies, and recent developments[J]. Organic Process Research & Process Research & Development, 2008, 12(2): 346-348.
Development, 2008, 12(2): 305-321. [26] Fernandez-Ibanez M Angeles, Macia Beatriz, Alonso Diego A, et al.
[4] Jacques Pelleter, Fabrice Renaud. Facile, fast and safe process Palladium and organocatalysis: An excellent recipe for asymmetric
development of nitration and bromination reactions using continuous synthesis[J]. Molecules (Basel, Switzerland), 2013, 18(9): 10108-10121.
flow reactors[J]. Organic Process Research & Development, 2009, [27] Finze Maik, Bernhardt Eduard, Willner Helge. Trifluoromethylboranes
13(4): 698-705. and -borates: New synthetic strategies and applications[J]. Angewandte
[5] Neal G Anderson. Practical use of continuous processing in Chemie (International edition), 2007, 46(48): 9100-9196.
developing and scaling up laboratory processes[J]. Organic Process [28] Pihko Petri M. Enantioselective alpha-fluorination of carbonyl
Research & Development, 2001, 5(6): 613-621. compounds: Organocatalysis or metal catalysis?[J]. Angewandte
[6] Makarshin L L, Pai Z P, Parmon V N. Microchannel systems for fine Chemie (International ed. in English), 2006, 45(4): 544-547.
organic synthesis[J]. Russian Chemical Reviews, 2016, 85(2): 139-155. [29] Hamashima Yoshitaka. Acid-base catalysis of chiral pd complexes:
[7] Helmut Pennemann, Volker Hessel, Holger Löwe. Chemical Development of novel asymmetric reactions[J]. Journal of the
microprocess technology—from laboratory-scale to production[J]. Pharmaceutical Society of Japan, 2005, 125(10): 785-793.
Chemical Engineering Science, 2004, 59(22/23): 4789-4794. [30] Keiji Nakayama, Duncan L Browne, Ian R Baxendale, et al. Studies
[8] Brian P Mason, Kristin E Price, Jeremy L Steinbacher, et al. Greener of a diastereoselective electrophilic fluorination reaction employinga
approaches to organic synthesis using microreactor technology[J]. cryo-flow reactor[J]. Synlett, 2013, 24(10): 1298-1302.
Chemical Reviews, 2007, 107(6): 2300-2318. [31] Jessica R Breen, Graham Sandford, Dmitrii S Yufit, et al. Continuous
[9] Patrick Löb, Holger Löwe, Volker Hessel. Fluorinations, chlorinations gas/liquid-liquid/liquid flow synthesis of 4-fluoropyrazole derivatives
an brominations of organic compounds in micro reactors[J]. Journal by selective direct fluorination[J]. Beilstein Journal of Organic
of Fluorine Chemistry, 2004, 125(11): 1677-1694. Chemistry, 2011, 7(120): 1048-1054.
[10] David Cantillo, C Oliver Kappe. Halogenation of organic compounds [32] Elgue Sebastien, Conte Annelyse, Gourdon Christophe, et al. Direct
using continuous flow and microreactor technology[J]. Reaction fluorination: 1,3-dicarbonyl compound in a continous flow reactor at
Chemistry & Engineering, 2017, 2(1): 7-19. industrial scale[J]. Chimica Oggi, 2012, 30(4): 18-21.
[11] Andrew R Bogdan, Sarah L Poe, Daniel C Kubis, et al. The [33] David A Nagib, Mark E Scott, David W C Macmillan.
continuous-flow synthesis of ibuprofen[J]. Angewandte Chemie Enantioselective α-trifluoromethylation of aldehydes via photoredox
International Edition, 2009, 48(45): 8547-8550. organocatalysis[J]. Journal of the American Chemical Society, 2009,
[12] Andrea Adamo, Rachel L Beingessner, Mohsen Behnam, et al. 131(31): 10875-10877.
On-demand continuous-flow production of pharmaceuticals in a [34] David Cantillo, Oscar De Frutos, Juan A Rincón, et al. A
compact, reconfigurable system[J]. Science,2016, 352(6281): 61-67. continuous-flow protocol for light-induced benzylic fluorinations[J].
[13] Lin Hongkun, Dai Chunhui, Timothy F Jamison, et al. A rapid total Journal of Organic Chemistry, 2014, 79(17): 8486-8490.
synthesis of ciprofloxacin hydrochloride in continuous flow[J]. [35] Bernhard Gutmann, David Cantillo, C Oliver Kappe. Continuous-flow
Angewandte Chemie International Edition, 2017, 56(30): 8870-8873. technology-a tool for the safe manufacturing of active pharmaceutical
ingredients[J]. Angewandte Chemie: International Edition, 2015,
[14] Graham Sandford. Elemental fluorine in organic chemistry 54(23): 6688-6728.
(1997-2006)[J]. Journal of Fluorine Chemistry, 2007, 128(2): 90-104. [36] Jérôme Baudoux. Electrophilic fluorination with N-F reagents[J].
[15] Li Guangxiao, Pu Xin, Shang Minjing, et al. Intensification of Organic Reactions (Hoboken, NJ, United States), 2007, 69: 347-672.
liquid-liquid two-phase mass transfer in a capillary microreactor [37] Xiao Ji Chang, Jean’ne M Shreeve. Microwave-assisted rapid
system[J]. AIChE Journal, 2019, 65(1): 334-346. electrophilic fluorination of 1,3-dicarbonyl derivatives with
[16] Charlotte Wiles, Paul Watts. Recent advances in micro reaction selectfluor[J]. Journal of Fluorine Chemistry, 2005, 126(4): 475-478.
technology[J]. Chemical Communications (Cambridge), 2011, 47(23): [38] Richard D Chambers, Mark A Fox, Darren Holling, et al. Elemental
6512-6535. fluorine part 16. Versatile thin-film gas-liquid multi-channel microreactors
[17] Marcus Baumann, Ian R Baxendale, Laetitia J Martin, et al. for effective scale-out[J]. Lab on A Chip, 2005, 5: 191-198.
Development of fluorination methods using continuous-flow [39] Teruo Umemoto, Shinji Fukami, Ginjiro Tomizawa, et al. Power and
microreactors[J]. Tetrahedron, 2009, 65(33): 6611-6625. structure-variable fluorinating agents, the n-fluoropyridinium salt
[18] Richard F Merritt. The polar fluorination of propenylbenzene[J]. system[J]. Journal of the American Chemical Society, 1990, 112(23):
Journal of the American Chemical Society, 1967, 89(3): 109-112. 8563-8575.
[19] Michael D Burkart, Zhang Zhiyuan , Hung Shang-Cheng , et al. A
new method for the synthesis of fluoro-carbohydrates and glycosides (下转第 587 页)