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Special Issue "Fluorine Chemistry 2016"

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

Deadline for manuscript submissions: closed (31 August 2016)

Special Issue Editor

Guest Editor
Prof. Dr. Bela Torok

Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston, MA 02125, USA
Website | E-Mail
Interests: organofluorine chemistry; heterogeneous catalysis; heterocyclic chemistry; asymmetric synthesis; catalytic hydrogenation; microwave-assisted organic synthesis; medicinal chemistry

Special Issue Information

Dear Colleagues,

Since the discovery of the beneficial effects of fluorine incorporation into organic molecules the synthesis and application of organofluorine compounds underwent an explosion like development. The major driving force of such developments was the pharmaceutical industry; however, organofluorine compounds are widely applied in many other applications from plastics, to refrigeration.
In this special issue, our goal is to provide an overview of this exciting research field, as broad as possible, highlighting recent developments in the design, synthesis and application of fluorine compounds.
It is our hope that this Special Issue on Fluorine Chemistry will become an attractive forum to scientists who either work on the synthesis of fluorinated compounds, or apply these compounds for different purposes. Thus this issue will be an excellent medium to present synthesis, structural analysis, pharmacological and therapeutic potential and other applications of fluorine compounds. I strongly encourage authors to submit papers for this Special Issue on Fluorine Chemistry, within the scope of Molecules. I hope that the topics covered will reflect the vast array of synthetic and application possibilities and generate potential future developments in this and related fields.

Dr. Bela Torok
Guest Editor

Submission

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a 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).

Keywords

  • fluorine
  • synthesis
  • medicinal chemistry
  • pharmacology
  • polymer
  • imaging
  • probe molecules
  • environmental
  • structural analysis
  • nanoparticles

Published Papers (16 papers)

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Research

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Open AccessArticle A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes
Molecules 2016, 21(11), 1493; doi:10.3390/molecules21111493
Received: 31 August 2016 / Revised: 19 September 2016 / Accepted: 4 November 2016 / Published: 17 November 2016
PDF Full-text (1093 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A novel selective and substrate-dependent synthetic protocol has been developed towards the synthesis of various fluorine-containing, highly functionalized cycloalkane derivatives. The method involves the stereoselective epoxidation of some unsaturated cyclic β-amino acid derivatives as model compounds, followed by a regioselective fluoride opening of
[...] Read more.
A novel selective and substrate-dependent synthetic protocol has been developed towards the synthesis of various fluorine-containing, highly functionalized cycloalkane derivatives. The method involves the stereoselective epoxidation of some unsaturated cyclic β-amino acid derivatives as model compounds, followed by a regioselective fluoride opening of oxiranes under various conditions with Deoxofluor and XtalFluor-E reagents, thereby offering an insight into this new epoxide opening methodology with fluoride. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy
Molecules 2016, 21(10), 1373; doi:10.3390/molecules21101373
Received: 9 September 2016 / Revised: 5 October 2016 / Accepted: 12 October 2016 / Published: 14 October 2016
PDF Full-text (5455 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In the present study, 3-(fluorobenzylideneamino)-6-chloro-1-(3,3-dimethylbutanoyl)-phenyl-2,3-dihydroquinazolin-4(1H)-one (FDQL) derivatives have been designed and synthesized to study the interaction between fluorine substituted dihydroquinazoline derivatives with human serum albumin (HSA) using fluorescence, circular dichroism and Fourier transform infrared spectroscopy. The results indicated that the FDQL
[...] Read more.
In the present study, 3-(fluorobenzylideneamino)-6-chloro-1-(3,3-dimethylbutanoyl)-phenyl-2,3-dihydroquinazolin-4(1H)-one (FDQL) derivatives have been designed and synthesized to study the interaction between fluorine substituted dihydroquinazoline derivatives with human serum albumin (HSA) using fluorescence, circular dichroism and Fourier transform infrared spectroscopy. The results indicated that the FDQL could bind to HSA, induce conformation and the secondary structure changes of HSA, and quench the intrinsic fluorescence of HSA through a static quenching mechanism. The thermodynamic parameters, ΔH, ΔS, and ΔG, calculated at different temperatures, revealed that the binding was through spontaneous and hydrophobic forces and thus played major roles in the association. Based on the number of binding sites, it was considered that one molecule of FDQL could bind to a single site of HSA. Site marker competition experiments indicated that the reactive site of HSA to FDQL mainly located in site II (subdomain IIIA). The substitution by fluorine in the benzene ring could increase the interactions between FDQL and HSA to some extent in the proper temperature range through hydrophobic effect, and the substitution at meta-position enhanced the affinity greater than that at para- and ortho-positions. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Effects of (Oxy-)Fluorination on Various High-Performance Yarns
Molecules 2016, 21(9), 1127; doi:10.3390/molecules21091127
Received: 17 August 2016 / Revised: 17 August 2016 / Accepted: 23 August 2016 / Published: 26 August 2016
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Abstract
In this work, typical high-performance yarns are oxy-fluorinated, such as carbon fibers, ultra-high-molecular-weight polyethylene, poly(p-phenylene sulfide) and poly(p-phenylene terephthalamide). The focus is on the property changes of the fiber surface, especially the wetting behavior, structure and chemical composition. Therefore,
[...] Read more.
In this work, typical high-performance yarns are oxy-fluorinated, such as carbon fibers, ultra-high-molecular-weight polyethylene, poly(p-phenylene sulfide) and poly(p-phenylene terephthalamide). The focus is on the property changes of the fiber surface, especially the wetting behavior, structure and chemical composition. Therefore, contact angle, XPS and tensile strength measurements are performed on treated and untreated fibers, while SEM is utilized to evaluate the surface structure. Different results for the fiber materials are observed. While polyethylene exhibits a relevant impact on both surface and bulk properties, polyphenylene terephthalamide and polyphenylene sulfide are only affected slightly by (oxy-)fluorination. The wetting of carbon fiber needs higher treatment intensities, but in contrast to the organic fibers, even its textile-physical properties are enhanced by the treatment. Based on these findings, the capability of (oxy-)fluorination to improve the adhesion of textiles in fiber-reinforced composite materials can be derived. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Fluorinated Polyurethanes, Synthesis and Properties
Molecules 2016, 21(7), 904; doi:10.3390/molecules21070904
Received: 7 June 2016 / Revised: 28 June 2016 / Accepted: 6 July 2016 / Published: 12 July 2016
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Abstract Fluorinated polyurethanes with a glass transition temperature as low as −139 °C and a decomposition onset temperature of 247–330 °C were prepared by a reaction of fluorinated alcohols with aromatic and cycloaliphatic diisocyanates in solution or melt. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Synthesis of Regiospecifically Fluorinated Conjugated Dienamides
Molecules 2014, 19(4), 4418-4432; doi:10.3390/molecules19044418
Received: 16 February 2014 / Revised: 22 March 2014 / Accepted: 31 March 2014 / Published: 10 April 2014
Cited by 4 | PDF Full-text (398 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Modular synthesis of regiospecifically fluorinated 2,4-diene Weinreb amides, with defined stereochemistry at both double bonds, was achieved via two sequential Julia-Kocienski olefinations. In the first step, a Z-a-fluorovinyl Weinreb amide unit with a benzothiazolylsulfanyl substituent at the allylic position was assembled. This
[...] Read more.
Modular synthesis of regiospecifically fluorinated 2,4-diene Weinreb amides, with defined stereochemistry at both double bonds, was achieved via two sequential Julia-Kocienski olefinations. In the first step, a Z-a-fluorovinyl Weinreb amide unit with a benzothiazolylsulfanyl substituent at the allylic position was assembled. This was achieved via condensation of two primary building blocks, namely 2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide (a Julia-Kocienski olefination reagent) and 2-(benzo[d]thiazol-2-ylthio)acetaldehyde (a bifunctional building block). This condensation was highly Z-selective and proceeded in a good 76% yield. Oxidation of benzothiazolylsulfanyl moiety furnished a second-generation Julia-Kocienski olefination reagent, which was used for the introduction of the second olefinic linkage via DBU-mediated condensations with aldehydes, to give (2Z,4E/Z)-dienamides in 50%–74% yield. Although olefinations were 4Z-selective, (2Z,4E/Z)-2-fluoro-2,4-dienamides could be readily isomerized to the corresponding 5-substituted (2Z,4E)-2-fluoro-N-methoxy-N-methylpenta-2,4-dienamides in the presence of catalytic iodine. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity
Molecules 2014, 19(2), 1763-1774; doi:10.3390/molecules19021763
Received: 2 January 2014 / Revised: 15 January 2014 / Accepted: 27 January 2014 / Published: 3 February 2014
Cited by 4 | PDF Full-text (237 KB) | HTML Full-text | XML Full-text
Abstract
The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases,
[...] Read more.
The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Open AccessArticle Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)
Molecules 2013, 18(12), 15737-15749; doi:10.3390/molecules181215737
Received: 13 November 2013 / Revised: 3 December 2013 / Accepted: 5 December 2013 / Published: 17 December 2013
Cited by 5 | PDF Full-text (776 KB) | HTML Full-text | XML Full-text
Abstract
Ni(II) complexes with N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2), N-4-fluorobenzoylpiperidine-1-carbothioimidate (L3), N-2-fluorobenzoylmorpholine- 1-carbothioimidate (L5) and N-4-fluorobenzoylmorpholine-1-carbothioimidate (L6)  have been synthesized and characterized by elemental analysis, FTIR and 1H-NMR. The crystal structures of three ligands (HL2, HL3
[...] Read more.
Ni(II) complexes with N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2), N-4-fluorobenzoylpiperidine-1-carbothioimidate (L3), N-2-fluorobenzoylmorpholine- 1-carbothioimidate (L5) and N-4-fluorobenzoylmorpholine-1-carbothioimidate (L6)  have been synthesized and characterized by elemental analysis, FTIR and 1H-NMR. The crystal structures of three ligands (HL2, HL3 and HL6) and the corresponding Ni(II) complexes ([Ni(L2)2], [Ni(L3)2] and [Ni(L6)2]) have been determined by X-ray diffraction. The antifungal activities of the Ni(II) complexes together and the corresponding ligands against the fungi Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp. have been investigated. The experimental results showed that the ligands and their complexes have antifungal abilities. When the fluorine was substituted on the para-benzoyl moiety, the antifungal activity of the ligands was obviously increased. Moreover, the ligands were stronger than their complexes in inhibiting fungal activities. The antifungal ability of HL6 is especially strong, and similar to that of the commercial fungicide fluconazole. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Open AccessArticle Synthesis of δ-Oxo-1,1-bis(triflyl)alkanes and Their Acidities
Molecules 2013, 18(12), 15531-15540; doi:10.3390/molecules181215531
Received: 4 November 2013 / Revised: 3 December 2013 / Accepted: 11 December 2013 / Published: 13 December 2013
Cited by 4 | PDF Full-text (300 KB) | HTML Full-text | XML Full-text
Abstract The reaction of 1,1-bis(triflyl)ethylene generated in situ with enolizable carbonyls yielded δ-oxo-1,1-bis(triflyl)alkane derivatives. Their acidities in both the gas and solution phases were determined. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Open AccessArticle Automated Solid-Phase Radiofluorination Using Polymer-Supported Phosphazenes
Molecules 2013, 18(9), 10531-10547; doi:10.3390/molecules180910531
Received: 24 July 2013 / Revised: 26 August 2013 / Accepted: 27 August 2013 / Published: 30 August 2013
Cited by 4 | PDF Full-text (1621 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The polymer supported phosphazene bases PS-P2tBu and the novel PS-P2PEG allowed for efficient extraction of [18F]F from proton irradiated [18O]H2O and subsequent radiofluorination of a broad range of substrates directly
[...] Read more.
The polymer supported phosphazene bases PS-P2tBu and the novel PS-P2PEG allowed for efficient extraction of [18F]F from proton irradiated [18O]H2O and subsequent radiofluorination of a broad range of substrates directly on the resin. The highest radiochemical yields were obtained with aliphatic sulfonates (69%) and bromides (42%); the total radiosynthesis time was 35–45 min. The multivariate analysis showed that the radiochemical yields and purities were controlled by the resin load, reaction temperature, and column packing effects. The resins could be reused several times with the same or different substrates. The fully automated on-column radiofluorination methodology was applied to the radiosynthesis of the important PET radiotracers [18F]FLT and [18F]FDG. The latter was produced with 40% yield on a 120 GBq scale and passed GMP-regulated quality control required for commercial production of [18F]FDG. The combination of compact form factor, simplicity of [18F]F recovery and processing, and column reusability can make solid phase radiofluorination an attractive radiochemistry platform for the emerging dose-on-demand instruments for bedside production of PET radiotracers. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Design and Synthesis of New N-(5-Trifluoromethyl)-1H-1,2,4-triazol-3-yl Benzenesulfonamides as Possible Antimalarial Prototypes
Molecules 2011, 16(9), 8083-8097; doi:10.3390/molecules16098083
Received: 1 August 2011 / Revised: 9 September 2011 / Accepted: 16 September 2011 / Published: 20 September 2011
Cited by 10 | PDF Full-text (706 KB)
Abstract
A rational approach was used to synthesize a new set of 15 1H-1,2,4-triazol-3-yl benzenesulfonamide derivatives with the aim of developing new antimalarial lead compounds. These derivatives were prepared in yields between 50% and 62%, and their structures were elucidated using IR,
[...] Read more.
A rational approach was used to synthesize a new set of 15 1H-1,2,4-triazol-3-yl benzenesulfonamide derivatives with the aim of developing new antimalarial lead compounds. These derivatives were prepared in yields between 50% and 62%, and their structures were elucidated using IR, 1H-, 13C-, 19F-NMR, MS and elemental analysis. A docking study based on sulfonamides previously used against malaria identified trifluoromethyl-substituted derivatives to be the best lead compounds for new antimalarial drug development. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessCommunication Synthesis of No-Carrier-Added 4-[18F]Fluorophenol from 4-Benzyloxyphenyl-(2-thienyl)iodonium Bromide
Molecules 2011, 16(9), 7621-7626; doi:10.3390/molecules16097621
Received: 11 August 2011 / Revised: 24 August 2011 / Accepted: 31 August 2011 / Published: 6 September 2011
Cited by 7 | PDF Full-text (402 KB)
Abstract
4-[18F]Fluorophenol is a versatile synthon for the synthesis of more complex radiopharmaceuticals bearing a 4-[18F]fluorophenoxy moiety. In order to prepare 4-[18F]fluorophenol in no-carrier-added (n.c.a.) form only a nucleophilic labelling method starting from [18F]fluoride is suitable.
[...] Read more.
4-[18F]Fluorophenol is a versatile synthon for the synthesis of more complex radiopharmaceuticals bearing a 4-[18F]fluorophenoxy moiety. In order to prepare 4-[18F]fluorophenol in no-carrier-added (n.c.a.) form only a nucleophilic labelling method starting from [18F]fluoride is suitable. In this paper a new, two step radiosynthesis starting from 4-benzyloxyphenyl-(2-thienyl)iodonium bromide and [18F]fluoride with subsequent deprotection is described, yielding n.c.a. [18F]fluorophenol in 34 to 36% radiochemical yield. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Open AccessArticle t-Bu2SiF-Derivatized D2-Receptor Ligands: The First SiFA-Containing Small Molecule Radiotracers for Target-Specific PET-Imaging
Molecules 2011, 16(9), 7458-7479; doi:10.3390/molecules16097458
Received: 28 July 2011 / Revised: 19 August 2011 / Accepted: 31 August 2011 / Published: 2 September 2011
Cited by 11 | PDF Full-text (616 KB)
Abstract
The synthesis, radiolabeling and in vitro evaluation of new silicon-fluoride acceptor (SiFA) derivatized D2-receptor ligands is reported. The SiFA-technology simplifies the introduction of fluorine-18 into target specific biomolecules for Positron-Emission-Tomography (PET). However, one of the remaining challenges, especially for small molecules
[...] Read more.
The synthesis, radiolabeling and in vitro evaluation of new silicon-fluoride acceptor (SiFA) derivatized D2-receptor ligands is reported. The SiFA-technology simplifies the introduction of fluorine-18 into target specific biomolecules for Positron-Emission-Tomography (PET). However, one of the remaining challenges, especially for small molecules such as receptor-ligands, is the bulkiness of the SiFA-moiety. We therefore synthesized four Fallypride SiFA-conjugates derivatized either directly at the benzoic acid ring system (SiFA-DMFP, SiFA-FP, SiFA-DDMFP) or at the butyl-side chain (SiFA-M-FP) and tested their receptor affinities. We found D2-receptor affinities for all compounds in the nanomolar range (Ki(SiFA-DMFP) = 13.6 nM, Ki(SiFA-FP) = 33.0 nM, Ki(SiFA-DDMFP) = 62.7 nM and Ki(SiFA-M-FP) = 4.21 nM). The radiofluorination showed highest yields when 10 nmol of the precursors were reacted with [18F]fluoride/TBAHCO3 in acetonitrile. After a reversed phased cartridge purification the desired products could be isolated as an injectable solution after only 10 min synthesis time with radiochemical yields (RCY) of more than 40% in the case of SiFA-DMFP resulting in specific activities >41 GBq/µmol (>1,100 Ci/mmol). Furthermore, the radiolabeled products were shown to be stable in the injectable solutions, as well as in human plasma, for at least 90 min. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
Open AccessArticle Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds
Molecules 2011, 16(8), 6512-6540; doi:10.3390/molecules16086512
Received: 27 June 2011 / Revised: 22 July 2011 / Accepted: 29 July 2011 / Published: 4 August 2011
Cited by 5 | PDF Full-text (932 KB)
Abstract
In this study we will present and discuss both the synthesis of CF2=CFCF2OSO2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C3F6/SO3 ratio, reaction temperature and boron catalyst/SO3
[...] Read more.
In this study we will present and discuss both the synthesis of CF2=CFCF2OSO2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C3F6/SO3 ratio, reaction temperature and boron catalyst/SO3 ratio on FAFS’ yield and selectivity, as well as a wide variety of ionic and radical reactions possible with FAFS. We focused our attention on reactions of FAFS with aliphatic and aromatic alcohols, acyl halides, halides, H2O2, ketones and radicals whose synthesis and reaction mechanisms will be presented and discussed. Particular attention will be devoted to the novel diallyl-fluoroalkyl peroxide obtained. Factors such as pKa and Lowry and Pearson’s Hard/Soft Acid-Base Theory which determine the selectivity between Addition/Elimination vs. Nucleophilic Substitution reaction mechanisms on FAFS will also be presented and discussed. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols
Molecules 2011, 16(5), 4031-4044; doi:10.3390/molecules16054031
Received: 23 March 2011 / Revised: 4 May 2011 / Accepted: 11 May 2011 / Published: 17 May 2011
PDF Full-text (258 KB)
Abstract
(Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformation, giving an 89%
[...] Read more.
(Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformation, giving an 89% yield of isomeric product mixture, was P2O5 in benzene at 80-90 °C. Products were characterized on the basis of their mass spectra and retention time information, and some peaks in the mass spectra were identified from their molecular fragments. Structures were assigned to the three most abundant products of (perfluorohexyl)tetramethylcyclopentenol dehydration. Formal dehydration kinetics showed a second order reaction in benzene but zeroth order with induction period in chlorobenzene, suggesting mass transfer limitations in the more polar chlorobenzene. Some of the products were formed by consecutive isomerization of the others, as shown by the kinetic analysis. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Open AccessArticle General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues
Molecules 2011, 16(4), 2817-2832; doi:10.3390/molecules16042817
Received: 15 February 2011 / Revised: 24 March 2011 / Accepted: 28 March 2011 / Published: 30 March 2011
Cited by 5 | PDF Full-text (250 KB)
Abstract
A convenient and general method for the synthesis in 26–73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R1)OR, where R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl,
[...] Read more.
A convenient and general method for the synthesis in 26–73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R1)OR, where R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), under mild conditions, is described. Another synthetic route also allowed the synthesis of 2-amino-5-trifluoromethyl-cycloalka[b][1,8]naphthyridines in 33–36% yields, from direct or indirect cyclo-condensation reactions of five-, six- and seven-membered 2-trifluoroacetyl-1-methoxy-cycloalkenes with 2,6-DAP. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Review

Jump to: Research

Open AccessReview Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis
Molecules 2011, 16(8), 6432-6464; doi:10.3390/molecules16086432
Received: 14 June 2011 / Revised: 5 July 2011 / Accepted: 19 July 2011 / Published: 29 July 2011
Cited by 30 | PDF Full-text (1157 KB)
Abstract
SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications as
[...] Read more.
SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications as a mediator in transformations of oxidizable functional groups or gold-catalyzed C-C and C-heteroatom oxidative coupling reactions, a catalyst in formation of various heterocyclic rings, a reagent or catalyst of various functionalizations of electron-rich organic compounds (iodination, bromination, chlorination, nitration, thiocyanation, sulfenylation, alkylation, alkoxylation), a catalyst of one-pot-multi-component coupling reactions, a catalyst of regioselective ring opening of epoxides, a deprotection reagent for various protecting groups, and a mediator for stereoselective rearrangement processes of bicyclic compounds are reviewed and discussed. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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