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Special Issue "Tri- and Di-Fluoromethylation and Tri- and Di-Fluoromethylchalcogenation Reactions"

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

Deadline for manuscript submissions: closed (30 April 2017)

Special Issue Editor

Guest Editor
Prof. Dr. Thierry Billard

Institute of Chemistry and Biochemistry (ICBMS - UMR CNRS 5246), Univ Lyon, Université Claude Bernard-Lyon 1, CNRS, Villeurbanne, France CERMEP - in vivo imaging, Groupement Hospitalier Est, Lyon, France
Website | E-Mail
Interests: fluorine chemistry; fluoroalkylchalcogenation; medicinal chemistry; radiochemistry; Fluorine-18; carbon-11; medical imaging

Special Issue Information

Dear Colleagues,

Because of the unique properties of fluorine atom, fluorinated compounds have shown growing interest in various fields of application. Among the fluorinated substituents, the CF3 and HCF2 groups have been particularly studied in recent years; in particular because of their potential benefits in life science. Furthermore, the association of these fluorinated parts with heteroatoms, and mainly chalcogens, have shown a particular interest due the obtained specific physico-chemical properties. Therefore, molecules bearing CF3O, CF3S, CF3Se, HCF2O, HCF2S and HCF2Se groups have been recently synthesized and studied. Such chemistry requires the development of new reagents and new methodologies to propose larger molecular diversity and complexity. The aim of this Special Issue is to gather research articles or reviews concerning, not only the development of new synthetic strategies to obtain these fluorinated molecules, but also the study of the properties and potential applications of these new compounds.

Prof. Dr. Thierry Billard
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 papers will be 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 monthly 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 1800 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

  • trifluoromethylation
  • difluoromethylation
  • trifluoromethylthiolation
  • difluoromethylthiolation
  • trifluoromethylselenolation
  • difluoromethylselenolation
  • trifluoromethoxylation
  • difluoromethoxylation

Published Papers (5 papers)

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Research

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Open AccessArticle Trifluoroethoxy-Coated Phthalocyanine Catalyzes Perfluoroalkylation of Alkenes under Visible-Light Irradiation
Molecules 2017, 22(7), 1130; doi:10.3390/molecules22071130
Received: 19 June 2017 / Revised: 1 July 2017 / Accepted: 3 July 2017 / Published: 7 July 2017
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Abstract
We disclose herein the perfluoroalkylation of alkenes catalyzed by trifluoroethoxy-coated zinc phthalocyanine under irradiation of visible light. Perfluoroalkyl iodides were nicely incorporated into unsaturated substrates, including alkyne, to provide perfluoroalkyl and iodide adducts in moderate to good yields. Trifluoromethylation is also possible by
[...] Read more.
We disclose herein the perfluoroalkylation of alkenes catalyzed by trifluoroethoxy-coated zinc phthalocyanine under irradiation of visible light. Perfluoroalkyl iodides were nicely incorporated into unsaturated substrates, including alkyne, to provide perfluoroalkyl and iodide adducts in moderate to good yields. Trifluoromethylation is also possible by trifluoromethyl iodide under the same reaction conditions. The mechanistic study is discussed. Full article
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Open AccessFeature PaperArticle Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity
Molecules 2017, 22(6), 966; doi:10.3390/molecules22060966
Received: 28 April 2017 / Revised: 6 June 2017 / Accepted: 6 June 2017 / Published: 9 June 2017
Cited by 1 | PDF Full-text (720 KB) | HTML Full-text | XML Full-text
Abstract
We describe the first gram scale preparation of the reagent dichlorotrifluoromethoxyacetic acid. This stable compound is obtained in five steps starting from the cheap diethylene glycol. The reactivity of the sodium salt of this fluorinated acid was also tested and allowed the preparation
[...] Read more.
We describe the first gram scale preparation of the reagent dichlorotrifluoromethoxyacetic acid. This stable compound is obtained in five steps starting from the cheap diethylene glycol. The reactivity of the sodium salt of this fluorinated acid was also tested and allowed the preparation of new amides. Full article
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Open AccessArticle Electrophilic Trifluoromethylselenolation of Boronic Acids
Molecules 2017, 22(5), 833; doi:10.3390/molecules22050833
Received: 1 May 2017 / Revised: 13 May 2017 / Accepted: 15 May 2017 / Published: 19 May 2017
Cited by 4 | PDF Full-text (1497 KB) | HTML Full-text | XML Full-text
Abstract
Trifluoromethylselenylated compounds are emergent compounds with interesting physicochemical properties that still suffer from a lack of efficient synthetic methods. We recently developed an efficient one-pot strategy to generate in situ CF3SeCl and use it in various reactions. Herein, we continue our
[...] Read more.
Trifluoromethylselenylated compounds are emergent compounds with interesting physicochemical properties that still suffer from a lack of efficient synthetic methods. We recently developed an efficient one-pot strategy to generate in situ CF3SeCl and use it in various reactions. Herein, we continue our study of the reactivity scope of this preformed reagent. Cross-coupling reactions with aromatic and heteroaromatic boronic acids have been investigated. The expected products have been obtained, using a stoichiometric amount of copper, with moderate yields. Full article
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Open AccessArticle Evaluation of Efficient and Practical Methods for the Preparation of Functionalized Aliphatic Trifluoromethyl Ethers
Molecules 2017, 22(5), 804; doi:10.3390/molecules22050804
Received: 28 April 2017 / Revised: 11 May 2017 / Accepted: 11 May 2017 / Published: 14 May 2017
Cited by 1 | PDF Full-text (5022 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The “chlorination/fluorination” technique for aliphatic trifluoromethyl ether synthesis was investigated and a range of products with various functional groups was prepared. The results were compared with oxidative desulfurization-fluorination of xanthates with the same structure. Full article
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Review

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Open AccessReview Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents
Molecules 2017, 22(6), 977; doi:10.3390/molecules22060977
Received: 20 May 2017 / Revised: 6 June 2017 / Accepted: 7 June 2017 / Published: 12 June 2017
Cited by 1 | PDF Full-text (6044 KB) | HTML Full-text | XML Full-text
Abstract
Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS) onto heterocycles. In this context, fluoroalkyl amino reagents (FARs)—a class
[...] Read more.
Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS) onto heterocycles. In this context, fluoroalkyl amino reagents (FARs)—a class of chemicals that was slightly forgotten over the last decades—has emerged again recently and proved to be a powerful tool for the introduction of various fluorinated groups onto (hetero)aromatic derivatives. Full article
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