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Fluorine Chemistry 2.0
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Fluorine Chemistry 2.0

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

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 8331

Special Issue Editors

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
Dr. Abdellatif Tikad

E-Mail Website
Guest Editor
Laboratoire de Chimie Moléculaire et Substances Naturelles, Faculté des Sciences, Université Moulay Ismail, B.P. 11201, Zitoune, Meknès 50050, Morocco
Interests: organic synthesis; steroids; heterocyclic chemistry; carbohydrate chemistry

Special Issue Information

Dear Colleagues,

Fluoride is a chemical element whose properties continue to stimulate the creativity of chemists, 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
Dr. Abdellatif Tikad
Guest Editors

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 (5 papers)

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Research

14 pages, 4716 KiB  
Article
Synthesis of CF3-Containing Spiro-[Indene-Proline] Derivatives via Rh(III)-Catalyzed C-H Activation/Annulation
by Alexandra S. Bubnova, Daria V. Vorobyeva, Ivan A. Godovikov, Alexander F. Smol’yakov and Sergey N. Osipov
Molecules 2023, 28(23), 7809; https://doi.org/10.3390/molecules28237809 - 27 Nov 2023
Viewed by 667
Abstract
An efficient method of accessing new CF3-containing spiro-[indene-proline] derivatives has been developed based on a Cp*Rh(III)-catalyzed tandem C-H activation/[3+2]–annulation reaction of 5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates with alkynes. An important feature of this spiro annulation process is the feasibility of dehydroproline moiety to [...] Read more.
An efficient method of accessing new CF3-containing spiro-[indene-proline] derivatives has been developed based on a Cp*Rh(III)-catalyzed tandem C-H activation/[3+2]–annulation reaction of 5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates with alkynes. An important feature of this spiro annulation process is the feasibility of dehydroproline moiety to act as a directing group in the selective activation of the aromatic C-H bond. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2.0)
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14 pages, 2041 KiB  
Article
Design and Synthesis of New α-hydroxy β-fluoro/β-trifluoromethyl and Unsaturated Phosphonates from Carbohydrate-Derived Building Blocks via Pudovik and Horner–Wadsworth–Emmons Reactions
by Monika Bilska-Markowska, Wojciech Jankowski, Marcin Hoffmann and Marcin Kaźmierczak
Molecules 2022, 27(17), 5404; https://doi.org/10.3390/molecules27175404 - 24 Aug 2022
Cited by 2 | Viewed by 1586
Abstract
Herein, we present the application of fluorinated carbohydrate-derived building blocks for α-hydroxy β-fluoro/β-trifluoromethyl and unsaturated phosphonates synthesis. Pudovik and Horner–Wadsworth–Emmons reactions were applied to achieve this goal. The proposed pathway of the key reactions is supported by the experimental results, as well as [...] Read more.
Herein, we present the application of fluorinated carbohydrate-derived building blocks for α-hydroxy β-fluoro/β-trifluoromethyl and unsaturated phosphonates synthesis. Pudovik and Horner–Wadsworth–Emmons reactions were applied to achieve this goal. The proposed pathway of the key reactions is supported by the experimental results, as well as quantum chemical calculations. The structure of the products was established by spectroscopic (1D, 2D NMR) and spectrometric (MS) techniques. Based on our data received, we claim that the progress of the Pudovik and HWE reactions is significantly influenced by the acidic protons present in the molecules as assessed by pKa values of the reagent. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2.0)
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18 pages, 5159 KiB  
Article
First Trifluoromethylated Phenanthrolinediamides: Synthesis, Structure, Stereodynamics and Complexation with Ln(III)
by Yuri A. Ustynyuk, Pavel S. Lemport, Vitaly A. Roznyatovsky, Konstantin A. Lyssenko, Alexey O. Gudovannyy, Petr I. Matveev, Ennie K. Khult, Mariia V. Evsiunina, Vladimir G. Petrov, Igor P. Gloriozov, Anton S. Pozdeev, Valentine S. Petrov, Nane A. Avagyan, Alexander S. Aldoshin, Stepan N. Kalmykov and Valentine G. Nenajdenko
Molecules 2022, 27(10), 3114; https://doi.org/10.3390/molecules27103114 - 12 May 2022
Cited by 12 | Viewed by 1854
Abstract
The first examples of 1,10-phenanthroline-2,9-diamides bearing CF3-groups on the side amide substituents were synthesized. Due to stereoisomerism and amide rotation, such complexes have complicated behavior in solutions. Using advanced NMR techniques and X-ray analysis, their structures were completely elucidated. The possibility [...] Read more.
The first examples of 1,10-phenanthroline-2,9-diamides bearing CF3-groups on the side amide substituents were synthesized. Due to stereoisomerism and amide rotation, such complexes have complicated behavior in solutions. Using advanced NMR techniques and X-ray analysis, their structures were completely elucidated. The possibility of the formation of complex compounds with lanthanoids nitrates was shown, and the constants of their stability are quantified. The results obtained are explained in terms of quantum-chemical calculations. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2.0)
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16 pages, 1519 KiB  
Article
Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2-a]pyrimidin-7-one Derivatives and Their Functionalization via Palladium-Catalyzed Reactions
by Wafa Blancou, Badr Jismy, Soufiane Touil, Hassan Allouchi and Mohamed Abarbri
Molecules 2022, 27(9), 3013; https://doi.org/10.3390/molecules27093013 - 7 May 2022
Cited by 1 | Viewed by 1646
Abstract
An efficient, versatile, and one-pot method for the preparation of novel fluorinated thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones is described from 2-aminothiazoles or 2-amino-oxazoles and fluorinated alkynoates. This transformation, performed under transition-metal-free conditions, offers new fluorinated cyclized products with good to excellent yields. Moreover, [...] Read more.
An efficient, versatile, and one-pot method for the preparation of novel fluorinated thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones is described from 2-aminothiazoles or 2-amino-oxazoles and fluorinated alkynoates. This transformation, performed under transition-metal-free conditions, offers new fluorinated cyclized products with good to excellent yields. Moreover, the functionalization of these N-fused scaffolds via the Suzuki-Miyaura and Sonogashira cross-coupling reactions led to the synthesis of highly diverse thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2.0)
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9 pages, 1548 KiB  
Article
Theoretical Prediction and Explanation of Reaction Site Selectivity in the Addition of a Phenoxy Group to Perfluoropyrimidine, Perfluoropyridazine, and Perfluoropyrazine
by Timothy J. Fuhrer, Matthew Houck, Rachel M. Chapman and Scott T. Iacono
Molecules 2021, 26(24), 7637; https://doi.org/10.3390/molecules26247637 - 16 Dec 2021
Cited by 1 | Viewed by 1721
Abstract
Perfluoroaromatics, such as perfluoropyridine and perfluorobenzene, are privileged synthetic scaffolds in organofluorine methodology, undergoing a series of regioselective substitution reactions with a variety of nucleophiles. This unique chemical behavior allows for the synthesis of many perfluoroaromatic derived molecules with unique and diverse architectures. [...] Read more.
Perfluoroaromatics, such as perfluoropyridine and perfluorobenzene, are privileged synthetic scaffolds in organofluorine methodology, undergoing a series of regioselective substitution reactions with a variety of nucleophiles. This unique chemical behavior allows for the synthesis of many perfluoroaromatic derived molecules with unique and diverse architectures. Recently, it has been demonstrated that perfluoropyridine and perfluorobenzene can be utilized as precursors for a variety of materials, ranging from high performance polyaryl ethers to promising drug scaffolds. In this work, using density functional theory, we investigate the possibility of perfluoropyrimidine, perfluoropyridazine, and perfluoropyrazine participating in similar substitution reactions. We have found that the first nucleophilic addition of a phenoxide group substitution on perfluoropyrimidine and on perfluoropyridazine would happen at a site para to one of the nitrogen atoms. While previous literature points to mesomeric effects as the primary cause of this phenomenon, our work demonstrates that this effect is enhanced by the fact that the transition states for these reactions result in bond angles that allow the phenoxide to π-complex with the electron-deficient diazine ring. The second substitution on perfluoropyrimidine and on perfluoropyridazine is most likely to happen at the site para to the other nitrogen. The second substitution on perfluoropyrazine is most likely to happen at the site para to the first substitution. The activation energies for these reactions are in line with those reported for perfluoropyridine and suggest that these platforms may also be worth investigation in the lab as possible monomers for high performance polymers. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2.0)
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