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Journal articles on the topic 'Fluorination'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Lantaño, Beatriz, and Al Postigo. "Radical fluorination reactions by thermal and photoinduced methods." Organic & Biomolecular Chemistry 15, no. 47 (2017): 9954–73. http://dx.doi.org/10.1039/c7ob02402a.

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Radical fluorination reactions of aliphatic Csp<sup>3</sup> and Csp<sup>2</sup> atoms, decarboxylative fluorination, and fluorination of (hetero)aromatics can be accomplished with electrophilic fluorinating reagents such as Selectfluor and NFSI.

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2

Bailey III, Wade H., William J. Casteel, and Robert G. Syvret. "Fluorination of Methyl 3-Oxopentanoate (MOP) Using Difluorobis(fluoroxy)methane, BDM." Collection of Czechoslovak Chemical Communications 67, no. 10 (2002): 1416–20. http://dx.doi.org/10.1135/cccc20021416.

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Difluorobis(fluoroxy)methane, BDM, is an electrophilic fluorinating agent that is capable of affecting selective monofluorination of 1,3-dicarbonyls such as diketones and ketoesters with very high regioselectivity. For example, in highly acidic anhydrous HF (AHF) solvent, fluorination of methyl 3-oxopentanoate (MOP) with BDM provides methyl 2-fluoro-3-oxopentanoate (MFOP) with 100% conversion and 95% selectivity. In mixtures of HF and methanol, fluorination conversions and selectivity are markedly lower. In comparison, direct fluorination of MOP with dilute F2 typically affords a fluorinated p

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3

Karelin, Vladimir A., Son Hai Le, Nadezhda V. Karelina, Alexander N. Strashko, Alexander V. Sazonov, and Huong M. T. Le. "Thermodynamics and Kinetics Research of the Fluorination Process of the Concentrate Rutile." Metals 12, no. 1 (2021): 34. http://dx.doi.org/10.3390/met12010034.

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The growth in the production of titanium metal and its compounds leads to an increase in the amount of toxic waste. As a result, at the legislative level, emissions of such wastes are limited, which leads to a drop in the production of titanium-containing products and a shortage of titanium in the international market. This paper presents the results of the process of fluorination of rutile concentrate from the Tarsky deposit (Russia, Omsk region) with elemental fluorine using a laboratory setup of a special design. For fluorination, samples of rutile concentrate weighing 0.1–1.0 g were used.

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4

Shibatomi, Kazutaka, Misaki Katada, Kazumasa Kitahara та Seiji Iwasa. "Catalyst-Free Decarboxylative Fluorination of Tertiary β-Keto Carboxylic Acids". Synlett 29, № 18 (2018): 2408–11. http://dx.doi.org/10.1055/s-0037-1611019.

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Decarboxylative fluorination of tertiary β-keto carboxylic acids was performed using an electrophilic fluorinating reagent. The reaction proceeded in the absence of a catalyst or base to yield the corresponding α-fluoroketones with tertiary fluorocarbons in good to high yields. Considering that the α-fluorination of asymmetrical ketones often causes problems with the regioselectivity between the α- and α′-positions, this method could be a good alternative to the α-fluorination of simple ketones for the synthesis of tertiary fluoroketones.

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5

Kharitonov, Alexander P., and Larisa N. Kharitonova. "Surface modification of polymers by direct fluorination: A convenient approach to improve commercial properties of polymeric articles." Pure and Applied Chemistry 81, no. 3 (2009): 451–71. http://dx.doi.org/10.1351/pac-con-08-06-02.

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The fundamental features and industrial applications of the direct fluorination of polymers are reviewed. Direct fluorination of polymers (i.e., treatment of a polymer surface with gaseous fluorine mixtures) proceeds spontaneously at room temperature and is a surface modification process. More than 25 polymers have been studied with the aid of a variety of analytical and spectroscopic techniques. The fundamental features of the direct fluorination, such as influence of treatment conditions (composition of the fluorinating mixture, fluorine partial pressure, temperature, and fluorination durati

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6

Haas, Alois, and Max Lieb. "Modern Synthetic Procedures for the Fluorination of Organic Molecules." CHIMIA 39, no. 5 (1985): 134. https://doi.org/10.2533/chimia.1985.134.

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In view of the number and diversity of publications on organofluorine chemistry in the recent years, it is evident that, since presenting the first series «Fluorierungsmethoden in der Organischen Chemie», fluorination reactions remain of general interest. The objectives of research in the various studies are quite similar. These include selective fluorination of biologically active substances such as steroids, nucleobases, pharmaceuticals, carbohydrates like sugars and glycosides; systematic studies for developing universally applicable fluorinating agents or improving reaction conditions; opt

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7

Cui, Benqiang, Shichong Jia, Etsuko Tokunaga, Norimichi Saito, and Norio Shibata. "Silver-induced self-immolative Cl–F exchange fluorination of arylsulfur chlorotetrafluorides: synthesis of arylsulfur pentafluorides." Chemical Communications 53, no. 95 (2017): 12738–41. http://dx.doi.org/10.1039/c7cc07222h.

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8

Oh, Young-Ho, Wonhyuck Yun, Chul-Hee Kim, et al. "Inter- and Intra-Molecular Organocatalysis of SN2 Fluorination by Crown Ether: Kinetics and Quantum Chemical Analysis." Molecules 26, no. 10 (2021): 2947. http://dx.doi.org/10.3390/molecules26102947.

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We present the intra- and inter-molecular organocatalysis of SN2 fluorination using CsF by crown ether to estimate the efficacy of the promoter and to elucidate the reaction mechanism. The yields of intramolecular SN2 fluorination of the veratrole substrates are measured to be very small (<1% in 12 h) in the absence of crown ether promoters, whereas the SN2 fluorination of the substrate possessing a crown ether unit proceeds to near completion (~99%) in 12 h. We also studied the efficacy of intermolecular rate acceleration by an independent promoter 18-crown-6 for comparison. We find that t

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9

Iskra, Jernej, Stojan Stavber, and Marko Zupan. "Fluorination of Fluorene, Dibenzofuran and Their Open Analogues with Caesium Fluoroxysulfate and Related Fluorinating Reagents." Collection of Czechoslovak Chemical Communications 73, no. 12 (2008): 1671–80. http://dx.doi.org/10.1135/cccc20081671.

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Fluorination of fluorene (1) with caesium fluoroxysulfate (CFS), 2,6-dichloro-1-fluoropyridinium tetrafluoroborate (FP-B800) and 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]- octane bis(tetrafluoroborate) (Accufluor NFTh) occurred only on the aromatic ring in the position ortho and para to the biphenyl central bond with the ratio 2-fluoro- (2a) vs 4-fluorofluorene (2b) 1.7-2.4:1. Regioselectivity of fluorination of both open-chain analogues - diphenylmethane (3a) and biphenyl (3b) was different and more ortho-fluorinated product was formed. Furthermore, the reaction of diphenylmethane (3a) wi

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10

Meublat, Laurent, Monique Lance, and Roland Bougon. "Reaction of RuO4 with KrF2: A clear-cut method to prepare ruthenium oxide tetrafluoride." Canadian Journal of Chemistry 67, no. 11 (1989): 1729–31. http://dx.doi.org/10.1139/v89-266.

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The fluorination of ruthenium tetroxide RuO4 was attempted by using either fluorine or krypton difluoride KrF2 in HF solution. Of the two fluorinating agents, only KrF2 was found to be powerful enough to react with RuO4 and to transform it into ruthenium oxide tetrafluoride RuOF4. This oxide fluoride of ruthenium VI was characterized by elemental analysis, X-ray powder diffraction, and infrared absorption spectroscopy. Keywords: ruthenium tetroxide, ruthenium oxide tetrafluoride, krypton difluoride, fluorination.

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11

Wang, Liyan, Xiaohuan Jiang, and Pingping Tang. "Silver-mediated fluorination of alkyl iodides with TMSCF3 as the fluorinating agent." Organic Chemistry Frontiers 4, no. 10 (2017): 1958–61. http://dx.doi.org/10.1039/c7qo00450h.

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12

LIU, YAQIANG, and LIQIANG LI. "EFFECTS OF DIRECT FLUORINATION ON SURFACE CONDUCTIVITY OF EPOXY RESIN INSULATORS." Surface Review and Letters 21, no. 06 (2014): 1450084. http://dx.doi.org/10.1142/s0218625x1450084x.

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Epoxy resin samples were surface fluorinated using a F 2/ N 2 mixture at different temperatures of 25°C, 55°C, 75°C, and 95°C for the same time. Attenuated total reflection infrared (ATR-IR) analyses indicate substantial changes in surface chemical composition and structure by the fluorinations. Scanning electron microscope (SEM) observations show an increase in thickness of the fluorinated layer and a change in its surface morphology with fluorination temperature. Conductivity measurements reveal a large increase in surface conductivity and surface potential measurements consistently show a l

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13

Lindič, Tilen, and Beate Paulus. "First-Principles Study of Adsorption of CH4 on a Fluorinated Model NiF2 Surface." Materials 17, no. 9 (2024): 2062. http://dx.doi.org/10.3390/ma17092062.

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Electrochemical fluorination on nickel anodes, also known as the Simons’ process, is an important fluorination method used on an industrial scale. Despite its success, the mechanism is still under debate. One of the proposed mechanisms involves higher valent nickel species formed on an anode acting as effective fluorinating agents. Here we report the first attempt to study fluorination by means of first principles investigation. We have identified a possible surface model from the simplest binary nickel fluoride (NiF2). A twice oxidized NiF2(F2) (001) surface exhibits higher valent nickel cent

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14

Ma, Long, Yufeng Li, Lingpei Meng, et al. "Correction: Biological fluorination from the sea: discovery of a SAM-dependent nucleophilic fluorinating enzyme from the marine-derived bacterium Streptomyces xinghaiensis NRRL B24674." RSC Advances 6, no. 93 (2016): 91024. http://dx.doi.org/10.1039/c6ra90088g.

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Correction for ‘Biological fluorination from the sea: discovery of a SAM-dependent nucleophilic fluorinating enzyme from the marine-derived bacterium Streptomyces xinghaiensis NRRL B24674’ by Long Ma et al., RSC Adv., 2016, 6, 27047–27051.

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15

Hintermann, Lukas, Mauro Perseghini та Antonio Togni. "Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters". Beilstein Journal of Organic Chemistry 7 (17 жовтня 2011): 1421–35. http://dx.doi.org/10.3762/bjoc.7.166.

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Titanium-based Lewis acids catalyze the α-fluorination of β-ketoesters by electrophilic N–F-fluorinating reagents. Asymmetric catalysis with TADDOLato–titanium(IV) dichloride (TADDOL = α,α,α',α'-tetraaryl-(1,3-dioxolane-4,5-diyl)-dimethanol) Lewis acids produces enantiomerically enriched α-fluorinated β-ketoesters in up to 91% enantiomeric excess, with either F–TEDA (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) in acetonitrile solution or NFSI (N-fluorobenzenesulfonimide) in dichloromethane solution as fluorinating reagents. The effects of various reaction p

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16

Remete, Attila Márió, Melinda Nonn, Santos Fustero, Matti Haukka, Ferenc Fülöp, and Loránd Kiss. "Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence." Beilstein Journal of Organic Chemistry 13 (November 6, 2017): 2364–71. http://dx.doi.org/10.3762/bjoc.13.233.

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A study exploring the chemical behavior of some dihydroxylated β-amino ester stereo- and regioisomers, derived from unsaturated cyclic β-amino acids is described. The nucleophilic fluorinations involving hydroxy–fluorine exchange of some highly functionalized alicyclic diol derivatives have been carried out in view of selective fluorination, investigating substrate dependence, neighboring group assistance and chemodifferentiation.

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17

Sun, Huan, Ji-Kai Liu, Si-Si Luo, et al. "Copper-Catalyzed Direct C-5 Fluorination of 8-Aminoquinolines by Remote C–H Activation." Synlett 29, no. 11 (2018): 1525–29. http://dx.doi.org/10.1055/s-0037-1610130.

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A convenient method was developed for direct regioselective fluorination of 8-aminoquinolines at the C-5 position by copper-catalyzed remote C–H activation using Selectfluor as the electrophile fluorinating reagent. With this method, diverse fluorinated quinoline derivatives were facilely obtained under mild conditions with moderate yields.

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18

Krivosudský, Lukáš, and Emma Mičejová. "Fluorination of vanadates with organic fluorinating agents." Journal of Fluorine Chemistry 271 (October 2023): 110193. http://dx.doi.org/10.1016/j.jfluchem.2023.110193.

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19

Liu, Youwei, Yuan Zhong, Xiang Lei, and Jinliang Wang. "Mechanism and Experimental Study on the Recovery of Rare Earth Elements from Neodymium Iron Boron Waste Using the ZnF2 Fluorination Method." Materials 17, no. 23 (2024): 5807. http://dx.doi.org/10.3390/ma17235807.

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We conducted a mechanistic and experimental study on zinc fluoride roasting for the recovery of NdFeB waste to address the difficulties faced during this pyrometallurgical recovery process, such as the high dependence on the quality of raw materials, the high energy consumption involved in roasting transformations, and the low added value of mixed rare earth products. Thermodynamic calculations showed the feasibility of fluorinating rare earths in NdFeB waste, and one-factor experiments were performed. The results showed that at a roasting temperature of 850 °C, a reaction time of 90 min, and

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20

Li, Zhi, Chengwei Zhan, Huan Yu, et al. "Study on the Fluorination Process of Sc2O3 by NH4HF2." Materials 16, no. 17 (2023): 5984. http://dx.doi.org/10.3390/ma16175984.

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Research on rare-earth fluorides is of urgent and critical importance for the preparation and emerging applications of high-purity alloys. The fluorination of Sc2O3 by NH4HF2 to fabricate ScF3 is investigated. The effects of the fluorination temperature, time and mass ratio of reactant on the fluorination rate and fluoride are discussed in this work. The fluorination reaction was first confirmed using thermodynamic calculation. The thermal and mass stability of the fluorination process were analyzed by thermogravimetric and differential scanning calorimetric (TG-DSC). The as-obtained products

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21

Zou, Liwei, Xiaoze Bao, Huanrui Zhang, Yuming Song, Jingping Qu та Baomin Wang. "Novel Tartrate-Based Guanidines for Enantioselective Fluorination of 1,3-Dicarbonyl and α-Cyano Carbonyl Compounds". Australian Journal of Chemistry 67, № 7 (2014): 1115. http://dx.doi.org/10.1071/ch14179.

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A novel library of chiral guanidines featuring the tartaric acid skeleton is easily accessed with tunable steric and electronic properties. A guanidine molecule of this library with an incorporated 2,6-diisoaniline fragment was identified as a suitable promoter for the enantioselective fluorination of 1,3-dicarbonyl and α-cyano carbonyl compounds to furnish the fluorinated product with up to 84 % ee and 99 % yield using N-fluorobenzenesulfonimide (NFSI) as the fluorinating agent.

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22

Differding, Edmond, and Robert W. Lang. "New fluorinating reagents - I. The first enantioselective fluorination reaction." Tetrahedron Letters 29, no. 47 (1988): 6087–90. http://dx.doi.org/10.1016/s0040-4039(00)82271-6.

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23

Guo, Zifeng, Meihua Hong, Yonghua Yu, et al. "Interventions to the Spontaneous Fabrication of Hierarchical ZSM-5 Zeolites by Fluorination-Alkaline Treatment." Catalysts 12, no. 9 (2022): 954. http://dx.doi.org/10.3390/catal12090954.

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The sequential fluorination-alkaline treatment protocol has been applied for the tailoring of siliceous ZSM-5 zeolite. The original spontaneous growth of mesoporosity in alkaline medium is altered due to the antecedent fluorination step. The outcome is demonstrated by the apparent delay in the mesoporosity growth, whose essential duration for the well-defined mesoporosity is therefore extended from 30 min to 60 min. A low fluorination level decelerates the mesoporosity growth, whereas a high fluorination level enables the achievement of the mesoporosity. These impacts are closely linked with t

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24

Komatsuda, Masaaki, Ayane Suto, Hiroki Kondo, et al. "Ring-opening fluorination of bicyclic azaarenes." Chemical Science 13, no. 3 (2022): 665–70. http://dx.doi.org/10.1039/d1sc06273e.

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A ring-opening fluorination of bicyclic azaarenes was developed. Although this overall transformation can be classified as an electrophilic fluorination of aromatics, it is a novel type of fluorination that results in construction of tert-C–F bonds.

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25

Furuta, Satoru, Manabu Kuroboshi, and Tamejiro Hiyama. "Fluorination of Orthothioesters through Oxidative Desulfurization–Fluorination." Bulletin of the Chemical Society of Japan 71, no. 8 (1998): 1939–51. http://dx.doi.org/10.1246/bcsj.71.1939.

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26

Zhang, W., M. Dubois, K. Guérin, et al. "Fluorinated nanocarbons using fluorinating agent: Strategies of fluorination and applications." European Physical Journal B 75, no. 2 (2009): 133–39. http://dx.doi.org/10.1140/epjb/e2009-00425-7.

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27

Zhang, Wei, Marc Dubois, Katia Guérin, and André Hamwi. "Fluorination of poly(p-phenylene) using TbF4 as fluorinating agent." Journal of Fluorine Chemistry 128, no. 11 (2007): 1402–9. http://dx.doi.org/10.1016/j.jfluchem.2007.07.002.

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28

Sandford, Graham. "Engineering fluorination." Nature Chemical Biology 5, no. 1 (2009): 6–7. http://dx.doi.org/10.1038/nchembio0109-6.

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29

Dolbier, W. R. "Fluorination Methods." Science 261, no. 5125 (1993): 1188–89. http://dx.doi.org/10.1126/science.261.5125.1188-a.

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30

DRAHL, CARMEN. "FLEXIBLE FLUORINATION." Chemical & Engineering News 87, no. 33 (2009): 7. http://dx.doi.org/10.1021/cen-v087n033.p007.

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31

Park, Oee Sook, Hoe Joo Son, and Woo Young Lee. "Allylic fluorination." Archives of Pharmacal Research 10, no. 4 (1987): 239–44. http://dx.doi.org/10.1007/bf02857747.

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32

Porhiel, Régis, Batiste Clavier, Taylan Karakoç, et al. "Fluorination Strategies for Mn₃O₄ Nanoparticles: Enhancing Reversibility and Capacity in Li-Ion Batteries." Batteries 11, no. 2 (2025): 53. https://doi.org/10.3390/batteries11020053.

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Transition metal oxides (TMOs) occupy an increasing share in the search for new electrode materials for Li-Ion batteries. Despite promising electrochemical performances (up to 1000 mAh g−1 in the case of conversion), these materials have poor cyclability linked primarily to hysteresis phenomena. To improve their electrochemical performance, one strategy consists of reducing the particle size. A second strategy relies on the incorporation of fluorine directly into electrode materials to limit the solid–electrolyte interface (SEI). Our study focuses on the impact of fluorination on the electroch

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33

Belov, Nikolay A., Aleksandr Yu Alentiev, Dmitrii S. Pashkevich, et al. "Hydrophobic–Hydrophilic Properties and Characterization of PIM-1 Films Treated by Elemental Fluorine in Liquid Perfluorodecalin." Polymers 14, no. 23 (2022): 5152. http://dx.doi.org/10.3390/polym14235152.

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A direct fluorination technique was applied for the surface treatment of PIM-1 films in a liquid phase (perfluorodecalin). The fluorinated samples were analyzed by various instrumental techniques. ATR-IR spectroscopy showed that the fluorination predominantly takes place in methylene- and methyl-groups. Cyano-groups, aromatic hydrogens and the aromatic structure of the PIM-1 repeat unit were shown to be relatively stable at the fluorination conditions. XPS confirmed that the concentration of fluorine, as well as oxygen, in the near surface layer (~1 nm) increases with fluorination time. C1s an

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34

You, Yang'en, Long Zhang та Sanzhong Luo. "Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis". Chemical Science 8, № 1 (2017): 621–26. http://dx.doi.org/10.1039/c6sc03109a.

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35

Yin, Bin, Shinsuke Inagi та Toshio Fuchigami. "Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts". Beilstein Journal of Organic Chemistry 11 (19 січня 2015): 85–91. http://dx.doi.org/10.3762/bjoc.11.12.

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Anodic fluorination of dithioacetals bearing electron-withdrawing ester, acetyl, amide, and nitrile groups at their α-positions was comparatively studied using various supporting poly(HF) salts like Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5). In the former two cases, the corresponding α-fluorination products or fluorodesulfurization products were obtained selectively depending on supporting poly(HF) salts used. In sharp contrast, in the latter two cases, fluorination product selectivity was strongly affected by the electron-withdrawing ability of α-substituents: A dithioacetal bearing a relati

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36

Ikawa, Takashi, Shigeaki Masuda, Tsuyoshi Nishiyama, Akira Takagi, and Shuji Akai. "Synthesis of Fluorinated Aromatic Compounds by One-Pot Benzyne Generation and Nucleophilic Fluorination." Australian Journal of Chemistry 67, no. 3 (2014): 475. http://dx.doi.org/10.1071/ch13548.

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The fluorination of substituted benzenes using fluoride ions under mild reaction conditions has been one of the most important challenges for the synthesis of biologically active fluorinated aromatic compounds; however, only a few synthetically useful methods are known. In this paper, it is reported that the nucleophilic fluorination of benzynes, generated from either 2-(trialkylsilyl)phenyl nonafluorobutanesulfonates or 2-(trialkylsilyl)phenols, meets this challenge. In particular, the fluorination starting from 2-(trialkylsilyl)phenols for fabricating aryl fluorides involves three sequential

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37

Oh, Young-Ho, Hyoju Choi, Chanho Park, Dong Wook Kim, and Sungyul Lee. "Harnessing Ionic Interactions and Hydrogen Bonding for Nucleophilic Fluorination." Molecules 25, no. 3 (2020): 721. http://dx.doi.org/10.3390/molecules25030721.

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We review recent works for nucleophilic fluorination of organic compounds in which the Coulombic interactions between ionic species and/or hydrogen bonding affect the outcome of the reaction. SN2 fluorination of aliphatic compounds promoted by ionic liquids is first discussed, focusing on the mechanistic features for reaction using alkali metal fluorides. The influence of the interplay of ionic liquid cation, anion, nucleophile and counter-cation is treated in detail. The role of ionic liquid as bifunctional (both electrophilic and nucleophilic) activator is envisaged. We also review the SNAr

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38

Wang, Feipeng, Li He, Muhammad Zeeshan Khan, et al. "Accelerated Charge Dissipation by Gas-Phase Fluorination on Nomex Paper." Applied Sciences 9, no. 18 (2019): 3879. http://dx.doi.org/10.3390/app9183879.

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The surface charge and space charge accumulation in paper used in oil–paper insulation system may distort electric field distribution and lead to the flashover and breakdown of insulation system. In this paper, the effect of gas-phase fluorination on the surface charge and space charge characteristics of oil-impregnated Nomex paper was investigated. Nomex T410 was fluorinated at 25 °C using F2/N2 mixtures with 20% F2 in volume at 0.05 MPa for 15, 30 and 45 min. Fourier Transform Infrared Spectroscopy (FTIR) proved that the molecular chain scission and cleavage occurred during gas-phase fluorin

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39

Belov, Nikolay A., Aleksandr Y. Alentiev, Dmitrii S. Pashkevich, et al. "Surface and Structural Characterization of PVTMS Films Treated by Elemental Fluorine in Liquid Perfluorodecalin." Materials 16, no. 3 (2023): 913. http://dx.doi.org/10.3390/ma16030913.

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Poly(vinyl trimethylsilane) (PVTMS) films were subjected to direct surface fluorination in liquid medium (perfluorodecalin). The samples were investigated using several techniques: SEM-XEDS, XPS, ATR-IR, and contact angle measurement. The methods used allowed us to estimate chemical changes occurring because of the treatment. ATR-IR showed that most of the changes occurred in the Si(CH3)3 group. Monofluorinated Si(CH3)3 groups formed in the near-surface layer (Ge crystal, 0.66 µm penetration) after 30 min of fluorination, and then di- and trifluorinated groups appeared. Oxidation of the film w

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40

Britton, Robert, and Michael Meanwell. "Synthesis of Heterobenzylic Fluorides." Synthesis 50, no. 06 (2018): 1228–36. http://dx.doi.org/10.1055/s-0036-1589159.

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Fluorination at heterobenzylic positions can have a significant impact on basicity, lipophilicity, and metabolism of drug leads. As a consequence, the development of new methods to access heterobenzylic fluorides has particular relevance to medicinal chemistry. This short review provides a survey of common methods used to synthesize heterobenzylic fluorides and includes fluoride displacement reactions of previously functionalized molecules (e.g., deoxyfluorination and halide exchange) and electrophilic fluorination of resonance-stabilized heterobenzylic anions. In addition, recent advances in

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41

Wu, Qiuzi, Yang-Jie Mao, Kun Zhou, et al. "Pd-Catalysed direct C(sp2)–H fluorination of aromatic ketones: concise access to anacetrapib." Chemical Communications 57, no. 37 (2021): 4544–47. http://dx.doi.org/10.1039/d1cc01047f.

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42

Jeffries, Benjamin, Zhong Wang, Robert I. Troup, et al. "Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups." Beilstein Journal of Organic Chemistry 16 (September 2, 2020): 2141–50. http://dx.doi.org/10.3762/bjoc.16.182.

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A systematic comparison of lipophilicity modulations upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl substituents, at a single carbon atom, is provided using directly comparable, and easily accessible model compounds. In addition, comparison with relevant linear chain derivatives is provided, as well as lipophilicity changes occurring upon chain extension of acyclic precursors to give cyclopropyl containing compounds. For the compounds investigated, fluorination of the isopropyl substituent led to larger lipophilicity modulation compared to fluorination of the cyclopropyl substituen

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Wang, Yafang, Liping Li, Xinsong Huang, Qi Li, and Guangshe Li. "New insights into fluorinated TiO2 (brookite, anatase and rutile) nanoparticles as efficient photocatalytic redox catalysts." RSC Advances 5, no. 43 (2015): 34302–13. http://dx.doi.org/10.1039/c4ra17076h.

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In this paper, we develop a fluorination methodology and optimize various synthesis conditions. We also demonstrate that photocatalytic redox activity is affected by the synergistic effect between surface fluorination and phase structure.

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FURUTA, S., M. KUROBOSHI, and T. HIYAMA. "ChemInform Abstract: Fluorination of Orthothioesters Through Oxidative Desulfurization-Fluorination." ChemInform 29, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199848049.

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Cordier, Christopher, Li-Jie Cheng, and Alexander Brown. "From Propargylic Fluorinations to [1,3]-Rearrangements: Anion and Ligand Effects in Cu-Acetylide Chemistry." Synlett 29, no. 13 (2018): 1675–82. http://dx.doi.org/10.1055/s-0036-1591997.

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Metal-catalyzed reactions of propargylic substrates have been widely studied. Of this reaction class, Cu-catalyzed methods have received much attention within the past decade, with Cu-allenylidenes being proposed as key reactive intermediates. This Synpacts article will outline our development of a nucleophilic fluorination protocol of propargylic electrophiles using copper catalysis. Following an analysis of the importance of anion and ligand effects, this study led us to the unexpected discovery of a formal [1,3]-rearrangement of O-propargylic alkoxypyridine derivatives that was later render

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Diksic, Mirko, Slmin Farrokhzad, and Lawrence D. Colebrook. "Fluorination of uracil with acetylhypofluorite and fluorine in acetic acid: mechanistic investigation." Canadian Journal of Chemistry 64, no. 2 (1986): 424–28. http://dx.doi.org/10.1139/v86-067.

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Fluorination of uracil with acetylhypofluorite and fluorine in acetic acid is described. The influence of the acetate ion on the products of the fluorination reaction was examined. Two stereoisomers (cis (3) and trans (4)) were found in the reaction mixture following fluorination in the absence of the acetate ion, but only one isomer (4) and 5-fluorouracil were found when the acetate ion was present during the fluorination reaction. 2H nuclear magnetic resonance revealed that acetate from the solution containing acetate ion rather than from the residue from acetylhypofluorite binds to position

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Kuribayashi, Shunsuke, Tomoyuki Kurioka, Shinsuke Inagi, Ho-Jung Lu, Biing-Jiun Uang, and Toshio Fuchigami. "The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives." Beilstein Journal of Organic Chemistry 14 (February 12, 2018): 389–96. http://dx.doi.org/10.3762/bjoc.14.27.

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We herein report that the regioselective anodic fluorination of S-alkyl benzothioate and its derivatives in various aprotic solvents using Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in moderate yields. Dichloromethane containing Et4NF·4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved.

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Wei, Xingxing, Pengyu Wang, Fen Liu, Xinshan Ye, and Decai Xiong. "Drug Discovery Based on Fluorine-Containing Glycomimetics." Molecules 28, no. 18 (2023): 6641. http://dx.doi.org/10.3390/molecules28186641.

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Glycomimetics, which are synthetic molecules designed to mimic the structures and functions of natural carbohydrates, have been developed to overcome the limitations associated with natural carbohydrates. The fluorination of carbohydrates has emerged as a promising solution to dramatically enhance the metabolic stability, bioavailability, and protein-binding affinity of natural carbohydrates. In this review, the fluorination methods used to prepare the fluorinated carbohydrates, the effects of fluorination on the physical, chemical, and biological characteristics of natural sugars, and the bio

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Yakubov, Shahboz, and Joshua P. Barham. "Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis." Beilstein Journal of Organic Chemistry 16 (September 3, 2020): 2151–92. http://dx.doi.org/10.3762/bjoc.16.183.

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The importance of fluorinated products in pharmaceutical and medicinal chemistry has necessitated the development of synthetic fluorination methods, of which direct C–H fluorination is among the most powerful. Despite the challenges and limitations associated with the direct fluorination of unactivated C–H bonds, appreciable advancements in manipulating the selectivity and reactivity have been made, especially via transition metal catalysis and photochemistry. Where transition metal catalysis provides one strategy for C–H bond activation, transition-metal-free photochemical C–H fluorination ca

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Janmanchi, Krishna Murthy, and William R. Dolbier, Jr. "Highly Reactive and Regenerable Fluorinating Agent for Oxidative Fluorination of Aromatics." Organic Process Research & Development 12, no. 2 (2008): 349–54. http://dx.doi.org/10.1021/op700266y.

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