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Fluorine Chemistry
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Fluorine Chemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 July 2020) | Viewed by 23295

Special Issue Editor

Prof. Dr. Mohamed Abarbri

E-Mail Website
Guest Editor
Laboratoire de Physico-Chimie des Matériaux et des Electrolytes Pour l’Energie (PCM2E), EA 6299, Avenue Monge, Faculté des Sciences, Université de Tours, Parc de Grandmont, 37200 Tours, France
Interests: synthesis of fluorinated compounds; synthesis of heterocyclic compounds; synthesis of compounds of biological interest; organic materials and development of new technologies for energy storage
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Fluoride is a chemical element whose properties continue to stimulate the creativity of chemists, and as well as stimulating new applications in different fields. The chemistry of fluorinated molecules has been growing in popularity over the past few years, and represents an important challenge for chemists. The introduction of a fluoro atom or a fluoroalkyl group in chemical compounds represents a major challenge for many organic chemists for the discovery of new molecules of interest, in particular agrochemical, therapeutic, and polymer.

In this Special Issue, our goal is to bring the public closer to the latest developments in this very specific research, and to collect significant advances in the synthesis of fluorinated molecules.

We hope that this Special Issue will be a research space for scientists working on the synthesis of fluorinated molecules, or using these compounds in different applications to highlight the recent developments in the design, synthesis, and application of fluorine compounds.

We strongly encourage authors to submit their publications for this Special Issue on Fluorine Chemistry. We hope that the field covered by this research will reflect a broad vision of synthetic and application possibilities, and will provide a solid base of data for future developments in this as well as in related fields.

Prof. Dr. Mohamed Abarbri
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Fluorine
  • Synthesis
  • Building block
  • Medicinal chemistry
  • Imaging
  • Materials

Published Papers (7 papers)

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Research

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20 pages, 2438 KiB  
Article
Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®
by Nadiia V. Pikun, Arkadij Sobolev, Aiva Plotniece, Martins Rucins, Brigita Vigante, Marina Petrova, Ruslan Muhamadejev, Karlis Pajuste and Yuriy G. Shermolovich
Molecules 2020, 25(14), 3143; https://doi.org/10.3390/molecules25143143 - 9 Jul 2020
Cited by 4 | Viewed by 3095
Abstract
New fluorinated 3,6-dihydropyridines were obtained by the electrophilic fluorination of 1,2-dihydropyridines with Selectfluor®. These 3-fluoro-3,6-dihydropyridines were easily converted to corresponding pyridines by the elimination of hydrogen fluoride under mild conditions. A new approach to the synthesis of methyl 2-(fluoromethyl)-5-nitro-6-arylnicotinates by the [...] Read more.
New fluorinated 3,6-dihydropyridines were obtained by the electrophilic fluorination of 1,2-dihydropyridines with Selectfluor®. These 3-fluoro-3,6-dihydropyridines were easily converted to corresponding pyridines by the elimination of hydrogen fluoride under mild conditions. A new approach to the synthesis of methyl 2-(fluoromethyl)-5-nitro-6-arylnicotinates by the fluorination of 3-fluoro-2-methyl-5-nitro-3,6-dihydropyridines or 1,2-dihydropyridines with Selectfluor® has been developed. Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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8 pages, 2603 KiB  
Communication
Molecular Structure Modulated Trap Distribution and Carrier Migration in Fluorinated Epoxy Resin
by Jin Li, Yufan Wang, Zhaoyu Ran, Hang Yao, Boxue Du and Tatsuo Takada
Molecules 2020, 25(13), 3071; https://doi.org/10.3390/molecules25133071 - 6 Jul 2020
Cited by 17 | Viewed by 2604
Abstract
Surface charge accumulation on epoxy insulators is one of the most serious problems threatening the operation safety of the direct current gas-insulated transmission line (GIL), and can be efficiently inhibited by the surface modification technology. This paper investigated the mechanisms of fluorination modulated [...] Read more.
Surface charge accumulation on epoxy insulators is one of the most serious problems threatening the operation safety of the direct current gas-insulated transmission line (GIL), and can be efficiently inhibited by the surface modification technology. This paper investigated the mechanisms of fluorination modulated surface charge behaviors of epoxy resin through quantum chemical calculation (QCC) analysis of the molecular structure. The results show that after fluorination, the surface charge dissipation process of the epoxy sample is accelerated by the introduced shallow trap sites, which is further clarified by the carrier mobility model. The electron distribution probability of the highest occupied molecular orbitals (HOMO) under positive charging and the lowest unoccupied molecular orbitals (LUMO) under negative charging shows distinctive patterns. It is illustrated that electrons are likely to aggregate locally around benzenes for the positively charged molecular structure, while electrons tend to distribute all along the epoxy chain under negatively charging. The calculated results verify that fluorination can modulate surface charge behaviors of epoxy resin through redesigning its molecular structure, trap distribution and charging patterns. Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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14 pages, 1320 KiB  
Article
Efficient Access to 3,5-Disubstituted 7-(Trifluoromethyl)pyrazolo[1,5-a]pyrimidines Involving SNAr and Suzuki Cross-Coupling Reactions
by Badr Jismy, Abdellatif Tikad, Mohamed Akssira, Gérald Guillaumet and Mohamed Abarbri
Molecules 2020, 25(9), 2062; https://doi.org/10.3390/molecules25092062 - 28 Apr 2020
Cited by 12 | Viewed by 3044
Abstract
An efficient and original synthesis of various 3,5-disubstituted 7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidines is reported. A library of compounds diversely substituted in C-3 and C-5 positions was easily prepared from a common starting material, 3-bromo-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-one. In C-5 position, a SNAr type [...] Read more.
An efficient and original synthesis of various 3,5-disubstituted 7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidines is reported. A library of compounds diversely substituted in C-3 and C-5 positions was easily prepared from a common starting material, 3-bromo-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-one. In C-5 position, a SNAr type reaction was achieved by first activating the C–O bond of the lactam function with PyBroP (Bromotripyrrolidinophosphonium hexafluorophosphate), followed by the addition of amine or thiol giving monosubstituted derivatives, whereas in C-3 position, arylation was performed via Suzuki–Miyaura cross-coupling using the commercially available aromatic and heteroaromatic boronic acids. Moreover, trifluoromethylated analogues of potent Pim1 kinase inhibitors were designed following our concise synthetic methodology. Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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17 pages, 3276 KiB  
Article
Fluorescent Submicron-Sized Poly(heptafluoro-n-butyl methacrylate) Particles with Long-Term Stability
by Maciej Jarzębski, Przemysław Siejak, Monika Przeor, Jacek Gapiński, Anna Woźniak, Hanna Maria Baranowska, Jarosław Pawlicz, Elżbieta Baryła-Pankiewicz and Anna Szwajca
Molecules 2020, 25(9), 2013; https://doi.org/10.3390/molecules25092013 - 25 Apr 2020
Cited by 2 | Viewed by 2545
Abstract
Fluorescent submicron particles of fluorinated methacrylate (HFMBA) with long-term stability have been synthesized and characterized with regard to their potential applications. Rhodamine B (RBITC) isothiocyanate was used as the fluorescent component. The core–shell structure of the particles effectively protected the dye against bleaching. [...] Read more.
Fluorescent submicron particles of fluorinated methacrylate (HFMBA) with long-term stability have been synthesized and characterized with regard to their potential applications. Rhodamine B (RBITC) isothiocyanate was used as the fluorescent component. The core–shell structure of the particles effectively protected the dye against bleaching. HFBMA nanoparticle (NP) stability was confirmed after seven years of storage. Only slight differences were found in the polydispersity index (pdi) from 0.002 to 0.010. Particle size measurements were carried out using dynamic light scattering (DLS), nanoparticle tracking (NTA), and fluorescence correlation spectroscopy (FCS). The hydrodynamic diameter evaluated by different methods were in good agreement, respectively: 184–550 nm, 218–579 nm, and 236–508 nm. Particle and core morphology was estimated by using scanning and transmission electron microscopy (SEM and TEM). The ability to recognize particles in 3D as a reference sample in biological media has been confirmed by epifluorescence optical microscopy, confocal laser scanning microscopy, and super-resolution confocal microscopy (STED). Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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Review

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19 pages, 2655 KiB  
Review
Importance of Fluorine in Benzazole Compounds
by Thuraya Al-Harthy, Wajdi Zoghaib and Raid Abdel-Jalil
Molecules 2020, 25(20), 4677; https://doi.org/10.3390/molecules25204677 - 14 Oct 2020
Cited by 35 | Viewed by 4290
Abstract
Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of [...] Read more.
Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed. Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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24 pages, 5018 KiB  
Review
Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review
by Albert Granados and Adelina Vallribera
Molecules 2020, 25(14), 3264; https://doi.org/10.3390/molecules25143264 - 17 Jul 2020
Cited by 12 | Viewed by 3697
Abstract
In this review, recent advances over the past decade in the preparation of fluorinated stereogenic quaternary centers on β-keto esters compounds are analyzed. Since the incorporation of fluorine and fluorinated groups is of special interest in pharmaceutical chemistry, a range of metal-catalyzed [...] Read more.
In this review, recent advances over the past decade in the preparation of fluorinated stereogenic quaternary centers on β-keto esters compounds are analyzed. Since the incorporation of fluorine and fluorinated groups is of special interest in pharmaceutical chemistry, a range of metal-catalyzed and organocatalyzed methods have been developed. Herein, we review the enantioselective fluorination, trifluoromethylation and trifluoromethylthiolation of 3-oxo esters. The scope, the induction of enantioselectivity and mechanistic investigations are presented. Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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13 pages, 6349 KiB  
Review
Harnessing Ionic Interactions and Hydrogen Bonding for Nucleophilic Fluorination
by Young-Ho Oh, Hyoju Choi, Chanho Park, Dong Wook Kim and Sungyul Lee
Molecules 2020, 25(3), 721; https://doi.org/10.3390/molecules25030721 - 7 Feb 2020
Cited by 11 | Viewed by 3034
Abstract
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 [...] Read more.
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 fluorination of diaryliodonium salts from the same perspective. Nucleophilic fluorination of guanidine-containing of diaryliodonium salts, which are capable of forming hydrogen bonds with the nucleophile, is exemplified as an excellent case where ionic interactions and hydrogen bonding significantly affect the efficiency of reaction. The origin of experimental observation for the strong dependence of fluorination yields on the positions of -Boc protection is understood in terms of the location of the nucleophile with respect to the reaction center, being either close to far from it. Recent advances in the synthesis of [18F]F-dopa are also cited in relation to SNAr fluorination of diaryliodonium salts. Discussions are made with a focus on tailor-making promoters and solvent engineering based on ionic interactions and hydrogen bonding. Full article
(This article belongs to the Special Issue Fluorine Chemistry)
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