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Organofluorine Chemistry
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Organofluorine Chemistry

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

Deadline for manuscript submissions: closed (30 April 2021) | Viewed by 22513

Special Issue Editors

Prof. Dr. Vito Capriati

E-Mail Website
Guest Editor
Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari "Aldo Moro, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy
Interests: organometallic chemistry; lithium carbenoic chemistry; green chemistry; deep eutectic solvents; water; cross-coupling reactions; heterogeneous catalysis; asymmetric synthesis; organoboron chemistry; organofluorine chemistry; heterocyclic chemistry; development of new sustainable chemical processes
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Yurii Yagupolskii

E-Mail Website
Guest Editor
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans’ka Str. 5, 02094 Kyiv, Ukraine
Interests: Organofluorine Chemistry; Synthetic Organic Chemistry; Organometallics; Heterocyclic Chemistry; Catalyst; Medicinal and Pharmaceutical Chemistry

Special Issue Information

Dear Colleagues,

Organofluorine chemistry,which represents an expanding field of research in drug design, has generated increasing interest in pharmaceutical research over the past decade. Although fluorinated organic molecules are virtually nonexistent in nature, the number of novel fluorine-containing substances as well as fluorinated drugs is ever increasing. It is expected that fluorinated small-molecular entities (azaheterocycles, functionalized alicycles, amino acids, nucleosides, etc.), as potential bioactive scaffolds or building blocks, will be of high importance in drug research over the coming years. Accordingly, their syntheses and the development of versatile synthetic methods for these types of derivatives have currently become a hot topic in synthetic organic and medicinal chemistry. Among the synthetic protocols towards fluorine-containing derivatives, either through nucleophilic or electrophilic late-stage fluorination or through the application of sophisticated fluorine-containing key elements, the access of various highly functionalized derivatives in view of selectivity, robustness, cost, efficiency, or applicability is still a significant challenge. I believe that synthetic fluorination methods as well as fluorine-containing structural elements presented in the submitted papers will be of interest not only to groups already involved in organofluorine chemistry but to the large community of synthetic and medicinal chemists, and that they will significantly affect future drug design. I am convinced that works published in this Special Issue of Molecules will further contribute to the advancement of organofluorine chemistry. Therefore, I strongly encurage fluorine chemists and the wider community of synthetic chemists to submit manuscripts for this Special Issue on Organofluorine Chemistry in the journal Molecules.

Prof. Dr. Loránd Kiss
Guest Editor

Manuscript Submission Information

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Keywords

  • Fluorine
  • Selective fluorinations
  • Fluorinated building blocks
  • Pharmaceutical fluorine chemistry
  • Late-stage fluorination
  • Fluorinating agents
  • Chirality
  • Asymmetric synthesis

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Published Papers (6 papers)

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Research

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12 pages, 1401 KiB  
Communication
Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes
by Laëtitia Chausset-Boissarie, Nicolas Cheval and Christian Rolando
Molecules 2020, 25(23), 5532; https://doi.org/10.3390/molecules25235532 - 25 Nov 2020
Cited by 3 | Viewed by 2152
Abstract
Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through [...] Read more.
Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted monofluoroalkenes in high yield, with good functional group tolerance, independently from the gem-bromofluoroalkenes geometry. Full article
(This article belongs to the Special Issue Organofluorine Chemistry)
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16 pages, 2490 KiB  
Article
Trifluoromethanesulfonamide vs. Non-Fluorinated Sulfonamides in Oxidative Sulfamidation of the C=C Bond: An In Silico Study
by Anton V. Kuzmin, Mikhail Yu. Moskalik and Bagrat A. Shainyan
Molecules 2020, 25(21), 4877; https://doi.org/10.3390/molecules25214877 - 22 Oct 2020
Cited by 5 | Viewed by 2504
Abstract
A theoretical analysis of the reaction of oxidative sulfamidation of several alkenes was performed in order to explain the various experimental observations and different reactivity of triflamide and non-fluorinated sulfonamides. Transformations occurring in the system alkene–sulfonamide in the presence of oxidative system (Bu [...] Read more.
A theoretical analysis of the reaction of oxidative sulfamidation of several alkenes was performed in order to explain the various experimental observations and different reactivity of triflamide and non-fluorinated sulfonamides. Transformations occurring in the system alkene–sulfonamide in the presence of oxidative system (ButOCl + NaI) were analyzed at the MP2/DGDZVP//B3LYP/DGDZVP level of theory using the IEF-PCM method for taking into account the solvent acetonitrile (MeCN) effect. As the model substrates, styrene, trimethyl(vinyl)silane, dimethyl(divinyl)silane and diphenyl(divinyl)silane were chosen and mesylamide, triflamide, tosylamide and p-nosylamide were taken as the reagents. ButOI generated from ButOCl and NaI reacts with sulfonamides to give N-iodinated sulfonamides RSO2NHI and RSO2NI2 as active intermediates, the iodinating activity of the latter being notably higher. The analysis allowed to answer such challenging questions as different reactivity of nonfluorinated sulfonamides leading to aziridination and of triflamide resulting in the formation the main products of bis-triflamidation, or different regioselectivity of halogenation of styrene and trimethyl(vinyl)silane caused by a linear intermediate iodonium cation in the former case and a cyclic one in the latter. Full article
(This article belongs to the Special Issue Organofluorine Chemistry)
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17 pages, 21039 KiB  
Article
Evaluation of Self-Assembly Pathways to Control Crystallization-Driven Self-Assembly of a Semicrystalline P(VDF-co-HFP)-b-PEG-b-P(VDF-co-HFP) Triblock Copolymer
by Enrique Folgado, Matthias Mayor, Vincent Ladmiral and Mona Semsarilar
Molecules 2020, 25(17), 4033; https://doi.org/10.3390/molecules25174033 - 3 Sep 2020
Cited by 7 | Viewed by 3816
Abstract
To date, amphiphilic block copolymers (BCPs) containing poly(vinylidene fluoride-co-hexafluoropropene) (P(VDF-co-HFP)) copolymers are rare. At moderate content of HFP, this fluorocopolymer remains semicrystalline and is able to crystallize. Amphiphilic BCPs, containing a P(VDF-co-HFP) segment could, thus be appealing for the [...] Read more.
To date, amphiphilic block copolymers (BCPs) containing poly(vinylidene fluoride-co-hexafluoropropene) (P(VDF-co-HFP)) copolymers are rare. At moderate content of HFP, this fluorocopolymer remains semicrystalline and is able to crystallize. Amphiphilic BCPs, containing a P(VDF-co-HFP) segment could, thus be appealing for the preparation of self-assembled block copolymer morphologies through crystallization-driven self-assembly (CDSA) in selective solvents. Here the synthesis, characterization by 1H and 19F NMR spectroscopies, GPC, TGA, DSC, and XRD; and the self-assembly behavior of a P(VDF-co-HFP)-b-PEG-b-P(VDF-co-HFP) triblock copolymer were studied. The well-defined ABA amphiphilic fluorinated triblock copolymer was self-assembled into nano-objects by varying a series of key parameters such as the solvent and the non -solvent, the self-assembly protocols, and the temperature. A large range of morphologies such as spherical, square, rectangular, fiber-like, and platelet structures with sizes ranging from a few nanometers to micrometers was obtained depending on the self-assembly protocols and solvents systems used. The temperature-induced crystallization-driven self-assembly (TI-CDSA) protocol allowed some control over the shape and size of some of the morphologies. Full article
(This article belongs to the Special Issue Organofluorine Chemistry)
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14 pages, 1634 KiB  
Article
Trifluoromethoxypyrazines: Preparation and Properties
by Taras M. Sokolenko and Yurii L. Yagupolskii
Molecules 2020, 25(9), 2226; https://doi.org/10.3390/molecules25092226 - 9 May 2020
Cited by 3 | Viewed by 3290
Abstract
The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a “pseudohalogen” character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, are less [...] Read more.
The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a “pseudohalogen” character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, are less studied. As trifluoromethoxy-substituted pyrazines are still unknown, we have developed efficient and scalable methods for 2-chloro-5-trifluoromethoxypyrazine synthesis, showing the synthetic utility of this molecule for Buchwald-Hartwig amination and the Kumada-Corriu and Suzuki and Sonogashira coupling reactions. Some comparisons of chlorine atom and trifluoromethoxy group stability in these transformations have been carried out. Full article
(This article belongs to the Special Issue Organofluorine Chemistry)
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20 pages, 3630 KiB  
Article
New Substituted Benzoylthiourea Derivatives: From Design to Antimicrobial Applications
by Carmen Limban, Mariana Carmen Chifiriuc, Miron Teodor Caproiu, Florea Dumitrascu, Marilena Ferbinteanu, Lucia Pintilie, Amalia Stefaniu, Ilinca Margareta Vlad, Coralia Bleotu, Luminita Gabriela Marutescu and Diana Camelia Nuta
Molecules 2020, 25(7), 1478; https://doi.org/10.3390/molecules25071478 - 25 Mar 2020
Cited by 23 | Viewed by 4328
Abstract
The increasing threat of antimicrobial resistance to all currently available therapeutic agents has urged the development of novel antimicrobials. In this context, a series of new benzoylthiourea derivatives substituted with one or more fluorine atoms and with the trifluoromethyl group have been tested, [...] Read more.
The increasing threat of antimicrobial resistance to all currently available therapeutic agents has urged the development of novel antimicrobials. In this context, a series of new benzoylthiourea derivatives substituted with one or more fluorine atoms and with the trifluoromethyl group have been tested, synthesized, and characterized by IR, NMR, CHNS and crystal X-ray diffraction. The molecular docking has provided information regarding the binding affinity and the orientation of the new compounds to Escherichia coli DNA gyrase B. The docking score predicted the antimicrobial activity of the studied compounds, especially against E. coli, which was further demonstrated experimentally against planktonic and biofilm embedded bacterial and fungal cells. The compounds bearing one fluorine atom on the phenyl ring have shown the best antibacterial effect, while those with three fluorine atoms exhibited the most intensive antifungal activity. All tested compounds exhibited antibiofilm activity, correlated with the trifluoromethyl substituent, most favorable in para position. Full article
(This article belongs to the Special Issue Organofluorine Chemistry)
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Review

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37 pages, 18179 KiB  
Review
Synthesis and Applications of Selected Fluorine-Containing Fluorophores
by Stefanie Casa and Maged Henary
Molecules 2021, 26(4), 1160; https://doi.org/10.3390/molecules26041160 - 22 Feb 2021
Cited by 22 | Viewed by 5284
Abstract
The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated [...] Read more.
The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated improvements in cell permeability, solubility, and other pharmacologic properties. For these and other numerous reasons, fluorination of molecules has grown in popularity in various fields of chemistry. Many reports show the effects observed from increasing the number of fluorine atoms on a fluorophore scaffold. This report will cover the most significant applications and improvements that fluorine has contributed to in various dye scaffolds such as BODIPY, rhodamine, phthalocyanine, and cyanine in the recent decade. Full article
(This article belongs to the Special Issue Organofluorine Chemistry)
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