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Themed collection Fluorine Chemistry

49 items
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Fluorine-18: an untapped resource in inorganic chemistry

Advances in the field of fluorine chemistry have been applied extensively to the syntheses of 18F-labelled organic compounds and radiopharmaceuticals.

Graphical abstract: Fluorine-18: an untapped resource in inorganic chemistry
From the themed collection: Fluorine Chemistry
Feature Article

Use of inorganic fluorinated materials in lithium batteries and in energy conversion systems

CFx-based materials bring significant improvement in terms of gravimetric and volumetric energy densities with respect to other types of primary Li batteries.

Graphical abstract: Use of inorganic fluorinated materials in lithium batteries and in energy conversion systems
From the themed collection: Fluorine Chemistry
Feature Article

Activation of C–F bonds α to C–C multiple bonds

A closer look is given to the successful approaches to the C(sp3)–F activation of benzylic, allylic, propargylic and allenylic fluorides.

Graphical abstract: Activation of C–F bonds α to C–C multiple bonds
From the themed collection: Fluorine Chemistry
Feature Article

Recent advances in the synthesis of functionalised monofluorinated compounds

Over the past few years, we have tackled the synthesis of interesting monofluorinated organic molecules, such as: dihydronaphthalene derivatives, β-fluoro sulfones and related carbonyl compounds, fluorohydrins and allylic alcohols.

Graphical abstract: Recent advances in the synthesis of functionalised monofluorinated compounds
From the themed collection: Fluorine Chemistry
Open Access Feature Article

Silicon-fluorine chemistry: from the preparation of SiF2 to C–F bond activation using silylenes and its heavier congeners

The feisty nature of silicon(II) fluorides has been harnessed by two cyclic alkyl amino carbene (cAAC) ligands and (cAAC)2SiF2 has been isolated at room temperature and structurally characterized.

Graphical abstract: Silicon-fluorine chemistry: from the preparation of SiF2 to C–F bond activation using silylenes and its heavier congeners
From the themed collection: Fluorine Chemistry
Review Article

Recent progress in photochemical radical di- and mono-fluoromethylation

Di- and mono-fluoromethyl radicals can be easily accessed by photochemical protocols.

Graphical abstract: Recent progress in photochemical radical di- and mono-fluoromethylation
From the themed collection: Fluorine Chemistry
Review Article

Chemistry of detrifluoroacetylatively in situ generated fluoro-enolates

This review article provides a summary of the detrifluoroacetylative in situ generation of fluorine-containing enolates and their related reactions.

Graphical abstract: Chemistry of detrifluoroacetylatively in situ generated fluoro-enolates
From the themed collection: Synthetic methodology in OBC
Communication

Radical fluoroalkylation reactions of (hetero)arenes and sulfides under red light photocatalysis

The use of Zn-phthalocyanine in a red-light-driven process for the perfluoroalkylation reactions of (hetero)arenes and sufides represents a friendlier environmental alternative.

Graphical abstract: Radical fluoroalkylation reactions of (hetero)arenes and sulfides under red light photocatalysis
From the themed collection: Fluorine Chemistry
Communication

Electrochemical trifluoromethylation/semipinacol rearrangement sequences of alkenyl alcohols: synthesis of β-CF3-substituted ketones

Electrochemical oxidative radical trifluoromethylation/semipinacol rearrangement sequences of alkenyl alcohols were developed in this study.

Graphical abstract: Electrochemical trifluoromethylation/semipinacol rearrangement sequences of alkenyl alcohols: synthesis of β-CF3-substituted ketones
From the themed collection: Synthetic methodology in OBC
Open Access Communication

Combined experimental and theoretical study of long-range H–F interactions in α-fluoro amides

A combined experimental and computational approach provided insight into the nature and conformational dependence of long-range 4JHF couplings in α-fluoro amides.

Graphical abstract: Combined experimental and theoretical study of long-range H–F interactions in α-fluoro amides
From the themed collection: Fluorine Chemistry
Communication

Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis

The BITE bioisostere of Et and CF3 allows lipophilicity to be tempered in analogues of the multiple sclerosis drug Gilenya®.

Graphical abstract: Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis
From the themed collection: Fluorine Chemistry
Open Access Communication

Neutral and cationic tungsten(VI) fluoride complexes with tertiary phosphine and arsine coordination

The dodecahedral [WF4{o-C6H4(EMe2)2}2]2+ dications (E = P, As) present the highest oxidation state metal fluoride complexes with soft donor ligands.

Graphical abstract: Neutral and cationic tungsten(vi) fluoride complexes with tertiary phosphine and arsine coordination
From the themed collection: Fluorine Chemistry
Communication

A degradable fluorinated surfactant for emulsion polymerization of vinylidene fluoride

An original degradable fluorinated surfactant, 3-hydroxy-2-(trifluoromethyl)propanoic acid was applied for the emulsion polymerization of vinylidene difluoride (VDF) to yield a latex of PVDF, consisted of typically 100 nm particle diameters.

Graphical abstract: A degradable fluorinated surfactant for emulsion polymerization of vinylidene fluoride
From the themed collection: Fluorine Chemistry
Communication

Reactivity and properties of bis(chlorodifluoroacetyl) peroxide generated in situ from chlorodifluoroacetic anhydride for chlorodifluoromethylation reactions

A practical one-pot procedure using chlorodifluoroacetic anhydride as a user-friendly chlorodifluoromethyl-source was developed.

Graphical abstract: Reactivity and properties of bis(chlorodifluoroacetyl) peroxide generated in situ from chlorodifluoroacetic anhydride for chlorodifluoromethylation reactions
From the themed collection: Fluorine Chemistry
Communication

A halogen bond-donor amino acid for organocatalysis in water

An XB-donor amino acid compound F(F4I) effectively promotes homogeneous catalysis of condensation reactions in water.

Graphical abstract: A halogen bond-donor amino acid for organocatalysis in water
From the themed collection: Fluorine Chemistry
Communication

C(sp2)–H Trifluoromethylation of enamides using TMSCF3: access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles

A method for the direct C(sp2)–H trifluoromethylation of enamides, including biologically relevant isoindolinones, isoquinolinones and 2-pyridinones using TMSCF3 under oxidative conditions is presented.

Graphical abstract: C(sp2)–H Trifluoromethylation of enamides using TMSCF3: access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles
From the themed collection: Fluorine Chemistry
Communication

Synthetic access to an elusive high-temperature perfluoroisopropenyl ether prepolymer for radical copolymerization

Generating a high yielding but strong fluorinated electrophile by destabilizing a low temperature perfluorocarbanion in non-polar solvent, while avoiding cascading side-reactions.

Graphical abstract: Synthetic access to an elusive high-temperature perfluoroisopropenyl ether prepolymer for radical copolymerization
From the themed collection: Fluorine Chemistry
Communication

Access towards enantiopure α,α-difluoromethyl alcohols by means of sulfoxides as traceless chiral auxiliaries

A new methodology has been developed to access highly enantioenriched α,α-difluoromethyl alcohols by means of sulfoxides as traceless and chiral auxiliaries.

Graphical abstract: Access towards enantiopure α,α-difluoromethyl alcohols by means of sulfoxides as traceless chiral auxiliaries
From the themed collection: Fluorine Chemistry
Communication

Dramatic enhancement of spin–spin coupling and quenching of magnetic dimensionality in compressed silver difluoride

The high-pressure HP2 form of AgF2 features Ag2F73− units that are theoretically predicted to host extremely strong antiferromagnetic interactions, surpassing those seen in copper(II) oxides.

Graphical abstract: Dramatic enhancement of spin–spin coupling and quenching of magnetic dimensionality in compressed silver difluoride
From the themed collection: Fluorine Chemistry
Open Access Communication

Fast and reliable generation of [18F]triflyl fluoride, a gaseous [18F]fluoride source

Reactive [18F]fluoride was generated from gaseous [18F]triflyl fluoride and used for a wide range of radiofluorination reactions.

Graphical abstract: Fast and reliable generation of [18F]triflyl fluoride, a gaseous [18F]fluoride source
From the themed collection: Fluorine Chemistry
Communication

Controlled hydroxy-fluorination reaction of anatase to promote Mg2+ mobility in rechargeable magnesium batteries

Fluorination of anatase as an effective way to tune Mg2+ intercalation properties.

Graphical abstract: Controlled hydroxy-fluorination reaction of anatase to promote Mg2+ mobility in rechargeable magnesium batteries
From the themed collection: Fluorine Chemistry
Communication

Visible-light promoted fluoroalkylselenolation: toward the reactivity of unsaturated compounds

α-Fluoroalkylselenolated sulfones have been readily obtained via a visible-light promoted radical addition of fluoroalkylselenyl and tosyl groups onto unsaturated substrates.

Graphical abstract: Visible-light promoted fluoroalkylselenolation: toward the reactivity of unsaturated compounds
From the themed collection: Fluorine Chemistry
Communication

Stereoselective aldol reactions using pseudo C2 symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione

Crossed aldol reactions of the CF3-containing pseudo C2 symmetric cyclic imide 3 were performed by way of the corresponding lithium and boron bisenolates to stereoselectively furnish the desired products 4.

Graphical abstract: Stereoselective aldol reactions using pseudo C2 symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione
From the themed collection: Fluorine Chemistry
Communication

Photochemical activation of SF6 by N-heterocyclic carbenes to provide a deoxyfluorinating reagent

A photochemical activation of SF6 provides access to difluoroimidazolidine derivatives, which can serve as intermediates to shuttle fluorides to alcohols by deoxyfluorination.

Graphical abstract: Photochemical activation of SF6 by N-heterocyclic carbenes to provide a deoxyfluorinating reagent
From the themed collection: Fluorine Chemistry
Communication

Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

Galactose-conjugated fluorinated and non-fluorinated proline oligomers were synthesized and evaluated as antifreeze molecules.

Graphical abstract: Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules
From the themed collection: Fluorine Chemistry
Communication

Synthesis of new fluorinated proline analogues from polyfluoroalkyl β-ketoacetals and ethyl isocyanoacetate

New straightforward synthetic approach to hitherto unknown cis-/trans-CF3-prolines and other 3-polyfluoroalkyl proline analogues.

Graphical abstract: Synthesis of new fluorinated proline analogues from polyfluoroalkyl β-ketoacetals and ethyl isocyanoacetate
From the themed collection: Fluorine Chemistry
Communication

Diels–Alder reactions of “in situ” generated perfluorinated thioketones

A simple and general procedure for the preparation of Diels–Alder adducts of perfluorinated thioketones and various dienes is reported.

Graphical abstract: Diels–Alder reactions of “in situ” generated perfluorinated thioketones
From the themed collection: Fluorine Chemistry
Communication

Tuning the Lewis acidity of difluorido gold(III) complexes: the synthesis of [AuClF2(SIMes)] and [AuF2(OTeF5)(SIMes)]

A route to [AuIIIClF2(SIMes)] and [AuIIIF2(OTeF5)(SIMes)] including structural characterization to tune the ligand arrangement and Lewis acidity of gold(III) centres was developed.

Graphical abstract: Tuning the Lewis acidity of difluorido gold(iii) complexes: the synthesis of [AuClF2(SIMes)] and [AuF2(OTeF5)(SIMes)]
From the themed collection: Fluorine Chemistry
Communication

The perfluorinated alcohols c-C6F11OH, c-C6F10-1,1-(OH)2 and c-C6F10-1-(CF3)OH

The thermally unstable α-fluoroalcohol undecafluorocyclohexanol (c-C6F11OH) was prepared by addition of hydrogen fluoride to the corresponding ketone.

Graphical abstract: The perfluorinated alcohols c-C6F11OH, c-C6F10-1,1-(OH)2 and c-C6F10-1-(CF3)OH
From the themed collection: Fluorine Chemistry
Communication

Oximinotrifluoromethylation of unactivated alkenes under ambient conditions

An oximinotrifluoromethylation of unactivated alkenes was developed via trifluoromethyl radical-induced intramolecular remote oximino migration under mild reaction conditions.

Graphical abstract: Oximinotrifluoromethylation of unactivated alkenes under ambient conditions
From the themed collection: Fluorine Chemistry
Communication

Highly C-selective difluoromethylation of β-ketoesters by using TMSCF2Br/lithium hydroxide/N,N,N-trimethylhexadecan-1-ammonium bromide

The first highly C-selective difluoromethylation of β-ketoesters was achieved by combining TMSCF2Br/LiOH/(CH3(CH2)15(CH3)3NBr).

Graphical abstract: Highly C-selective difluoromethylation of β-ketoesters by using TMSCF2Br/lithium hydroxide/N,N,N-trimethylhexadecan-1-ammonium bromide
From the themed collection: Fluorine Chemistry
Communication

The CF3-DAST-induced deacylative trifluoromethylthiolation of cyclic 1,3-diketones/lactams/lactones and its extension to deacylative pentafluorophenylthiolation

CF3-DAST-induced deacylative trifluoromethylthiolation of cyclic 1,3-diketones lactams, and lactones that provides cyclic trifluoromethylthioketones, lactams and lactones is reported.

Graphical abstract: The CF3-DAST-induced deacylative trifluoromethylthiolation of cyclic 1,3-diketones/lactams/lactones and its extension to deacylative pentafluorophenylthiolation
From the themed collection: Fluorine Chemistry
Communication

Copper-mediated intramolecular aminofluorination of 1,3-dienes by using nucleophilic fluorine reagents

A copper-mediated intramolecular aminofluorination of 1,3-dienes is disclosed, in which both AgF and Et3N·3HF can be used as the fluorine source.

Graphical abstract: Copper-mediated intramolecular aminofluorination of 1,3-dienes by using nucleophilic fluorine reagents
From the themed collection: Fluorine Chemistry
Communication

Fluorinated cyclopropanes: synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

A general route to aryl α,β,β-trifluorocyclopropanes is reported and aryl oxidation gave the corresponding α,β,β-trifluorocyclopropane carboxylic acid.

Graphical abstract: Fluorinated cyclopropanes: synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif
From the themed collection: Fluorine Chemistry
Communication

Stille cross-coupling of secondary and tertiary α-(trifluoromethyl)-benzyl chlorides with allylstannanes

A Stille cross-coupling reaction was developed for the first time by secondary (trifluoromethyl)benzyl chlorides and allylstannanes.

Graphical abstract: Stille cross-coupling of secondary and tertiary α-(trifluoromethyl)-benzyl chlorides with allylstannanes
From the themed collection: Fluorine Chemistry
Communication

Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre via the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates

The Pd-catalyzed asymmetric decarboxylative allylic alkylation of trifluoromethoxy allyl enol carbonates is disclosed.

Graphical abstract: Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre via the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates
From the themed collection: Fluorine Chemistry
Open Access Communication

Minimising conformational bias in fluoroprolines through vicinal difluorination

Combining the 4S-fluoro and 3R-fluoromotifs, which each instill an opposing conformational bias, leads to a fluorinated proline with a similar conformational profile to proline.

Graphical abstract: Minimising conformational bias in fluoroprolines through vicinal difluorination
From the themed collection: Fluorine Chemistry
Communication

Stereodivergent trifluoromethylation of N-sulfinylimines by fluoroform with either organic-superbase or organometallic-base

The first stereodivergent trifluoromethylation of N-sulfinylimines by fluoroform is reported.

Graphical abstract: Stereodivergent trifluoromethylation of N-sulfinylimines by fluoroform with either organic-superbase or organometallic-base
From the themed collection: Fluorine Chemistry
Open Access Communication

A rhodium-catalyzed transannulation of N-(per)fluoroalkyl-1,2,3-triazoles under microwave conditions – a general route to N-(per)fluoroalkyl-substituted five-membered heterocycles

An efficient rhodium-catalyzed microwave-assisted transannulation of N-(per)fluoroalkyl-1,2,3-triazoles to previously inaccessible N-(per)fluoroalkyl five-membered heterocycles was developed.

Graphical abstract: A rhodium-catalyzed transannulation of N-(per)fluoroalkyl-1,2,3-triazoles under microwave conditions – a general route to N-(per)fluoroalkyl-substituted five-membered heterocycles
From the themed collection: Fluorine Chemistry
Communication

Photoredox generation of the trifluoromethyl radical from borate complexes via single electron reduction

A trifluoromethyl radical is generated by single electron reduction of CF3-substituted borate complexes.

Graphical abstract: Photoredox generation of the trifluoromethyl radical from borate complexes via single electron reduction
From the themed collection: Fluorine Chemistry
Paper

Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion

1,1-Difluoroallenes underwent β-selective C–C bond formation (insertion) via π-allylpalladium(II) to facilitate aromatic ring construction, leading to biologically promising (difluoromethyl)naphthalenes.

Graphical abstract: Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion
From the themed collection: Synthetic methodology in OBC
Paper

Fluoroalkenylation of boronic acids via an oxidative Heck reaction

A fluoroalkenylation of boronic acids with fluoroalkyl alkenes has been developed.

Graphical abstract: Fluoroalkenylation of boronic acids via an oxidative Heck reaction
From the themed collection: Synthetic methodology in OBC
Paper

Visible-light-induced radical trifluoromethylthiolation of N-(o-cyanobiaryl)acrylamides

Visible-light-mediated trifluoromethylthiolation of N-(o-cyanobiaryl)acrylamides with N-trifluoromethylthiosaccharin as the source of SCF3 radicals provided an efficient route to SCF3-containing ring-fused phenanthridine derivatives.

Graphical abstract: Visible-light-induced radical trifluoromethylthiolation of N-(o-cyanobiaryl)acrylamides
From the themed collection: Synthetic methodology in OBC
Paper

Lewis acid promoted fluorine-alkoxy group exchange reactions for the synthesis of 5-alkoxy-4,4-difluoroisoxazoline systems

Lewis acid promoted substitution of fluorine yields novel 5-alkoxylated 4,4-difluoroisoxazolines via SN1 type processes.

Graphical abstract: Lewis acid promoted fluorine-alkoxy group exchange reactions for the synthesis of 5-alkoxy-4,4-difluoroisoxazoline systems
From the themed collection: Synthetic methodology in OBC
Open Access Paper

Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions

Herein we introduce tetrafluoropyridyl (TFP) as a new general protecting group for phenols. The TFP protecting group is readily cleaved under mild conditions.

Graphical abstract: Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions
From the themed collection: Synthetic methodology in OBC
Paper

Tuning the properties of a cyclic RGD-containing tetrapeptide through backbone fluorination

Fluorination alters a cyclic peptide's synthetic efficiency, its molecular conformation, and its biological activity.

Graphical abstract: Tuning the properties of a cyclic RGD-containing tetrapeptide through backbone fluorination
From the themed collection: Fluorine Chemistry
Paper

Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

An efficient Brønsted base-catalyzed Pechmann-type reaction of cyclic 1,3-diones with ethyl 4,4,4-trifluoroacetoacetate to afford 4-trifluoromethyl 2-pyrones and pyridones was developed.

Graphical abstract: Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones
From the themed collection: Synthetic methodology in OBC
Paper

Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol

Hexafluoroisopropan-2-ol is an excellent solvent for promoting fluorinations with the stable hypervalent fluoroiodane reagent without any transition metals or TREAT-HF activators.

Graphical abstract: Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment

The aerobic oxidation took place after the visible light-mediated ring-opening reaction of gem-difluorocyclopropane in the presence of an organic dye and amine to furnish 2,2-difluoro-homoallylic alcohols in good yields.

Graphical abstract: Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment
From the themed collection: Synthetic methodology in OBC
49 items

About this collection

This collection, Guest Edited by ChemComm Chair Professor Veronique Gourvernor, has been created to compliment the 22nd International Symposium on Fluorine Chemistry. This collection is dedicated to all aspects of fluorine chemistry, celebrating the field’s current achievements and future perspectives. New articles will be added to this collection as they are published.

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