Jump to main content
Jump to site search

Themed collection Fluorine Chemistry

26 items
Communication

Reversible hydrocarbon/perfluorocarbon phase-switching of [Ru(bipy)3]2+ driven by supramolecular heteromeric fluorous carboxylate–carboxylic acid H-bond interactions

Self-assembly of a highly fluorous anion leads to quantitative phase transfer of the photo- and electroactive pristine dicationic Ru(bipy)32+ into apolar perfluorinated solvent.

Graphical abstract: Reversible hydrocarbon/perfluorocarbon phase-switching of [Ru(bipy)3]2+ driven by supramolecular heteromeric fluorous carboxylate–carboxylic acid H-bond interactions
From the themed collection: Fluorine Chemistry
Communication

Fluorous tagging of DABCO through halogen bonding: recyclable catalyst for the Morita–Baylis–Hillman reaction

The halogen-bonded adduct between DABCO and two molecules of perfluorooctyl iodide (DABCO·(C8F17I)2) acts as a recyclable fluorous organocatalyst for the Morita–Baylis–Hillman reaction.

Graphical abstract: Fluorous tagging of DABCO through halogen bonding: recyclable catalyst for the Morita–Baylis–Hillman reaction
From the themed collection: Fluorine Chemistry
Communication

Fluorous benzaldehyde-based synthesis of biaryl-substituted oxazabicyclo[3.3.1]nonanes

Fluorous benzaldehyde-based synthesis of biaryl-substituted oxazabicyclo[3.3.1]nonanes is accomplished by a three-step synthesis including a multicomponent reaction (MCR) to form tetrahydroquinoline, followed by cycloaddition with coumarin to form oxazabicycles, and then a Suzuki coupling to introduce the biaryl group. Microwave irradiation and fluorous solid-phase extraction (F-SPE) are employed to speed up reactions and simplify product purification.

Graphical abstract: Fluorous benzaldehyde-based synthesis of biaryl-substituted oxazabicyclo[3.3.1]nonanes
From the themed collection: Fluorine Chemistry
Communication

Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach

The synthesis of 8-aminoquinolines and 1,10-phenanthrolines with substituents in α of the nitrogen atoms has been performed through an inverse-demanding aza-Diels–Alder in the fluorinated alcohols TFE or HFIP.

Graphical abstract: Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach
From the themed collection: Fluorine Chemistry
Communication

Chemical tailoring of fullerene acceptors: synthesis, structures and electrochemical properties of perfluoroisopropylfullerenes

Linear correlation between the measured E1/2 values and DFT-calculated LUMO energies for ten fullerene(i-C3F7)n compounds with n = 2–6.

Graphical abstract: Chemical tailoring of fullerene acceptors: synthesis, structures and electrochemical properties of perfluoroisopropylfullerenes
From the themed collection: Fluorine Chemistry
Communication

Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate

An efficient method for highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids and related derivatives was developed via indium-mediated allylation of (R)-phenylglycinol methyl ether based imines of trifluoropyruvate in good yields with high diastereoselectivities.

Graphical abstract: Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate
From the themed collection: Fluorine Chemistry
Communication

Fluorous diastereomeric mixture synthesis (FDMS) of hydantoin-fused hexahydrochromeno[4,3-b]pyrroles

Fluorous diastereomeric mixture synthesis (FDMS) is introduced and demonstrated in the synthesis of six diastereomers of hydantoin-fused hexahydrochromeno[4,3-b]pyrroles.

Graphical abstract: Fluorous diastereomeric mixture synthesis (FDMS) of hydantoin-fused hexahydrochromeno[4,3-b]pyrroles
From the themed collection: Fluorine Chemistry
Communication

Straightforward synthesis of enantiopure (R)- and (S)-trifluoroalaninol

Enantiopure (R)- and (S)-trifluoroalaninol were conveniently synthesized in a few steps from fluoral hemiacetal or ethyl trifluoropyruvate.

Graphical abstract: Straightforward synthesis of enantiopure (R)- and (S)-trifluoroalaninol
From the themed collection: Fluorine Chemistry
Communication

Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of D-glucose and D-altrose and assessment of their erythrocyte transmembrane transport

The 2,3,4-trifluoro-2,3,4-tridehydroxy hexose analogues of D-glucose and D-altrose were prepared and structurally characterised and the novel sugar analogues were explored by 2D-19F-EXSY NMR for their potential to cross erythrocyte (red blood cell) membranes.

Graphical abstract: Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of d-glucose and d-altrose and assessment of their erythrocyte transmembrane transport
From the themed collection: Fluorine Chemistry
Communication

1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid

In situ-generated silyl methide species catalyzed the diastereoselective 1,4-addition reaction of silicon dienoates such as 3-bromo-2-silyloxyfuran to α,β-unsaturated aldehydes.

Graphical abstract: 1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid
From the themed collection: Fluorine Chemistry
Letter

Synthesis, characterization, and applications of fluorous resorcin[4]arenes

The fluorous resorcin[4]arene immobilized in a fluorous bulk membrane is capable of transporting tetramethylammonium cation from an aqueous source phase into an aqueous receiving phase.

Graphical abstract: Synthesis, characterization, and applications of fluorous resorcin[4]arenes
From the themed collection: Fluorine Chemistry
Edge Article

Convergent 18F radiosynthesis: A new dimension for radiolabelling

Structurally diverse 18F-labelled molecular scaffolds are now accessible in one step combining an 18F-component with two or more additional building blocks. This approach is easy to implement and leads to a series of novel 18F products difficult to access by known methods.

Graphical abstract: Convergent 18F radiosynthesis: A new dimension for radiolabelling
From the themed collection: Fluorine Chemistry
Paper

TBAF-Catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: access to arylpyridines and bihetaryl compounds

Silver oxide and catalytic TBAF efficiently promoted the coupling of functional trimethylsilylpyridines with (hetero)aromatic halides.

Graphical abstract: TBAF-Catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: access to arylpyridines and bihetaryl compounds
From the themed collection: Fluorine Chemistry
Paper

A recyclable perfluoroalkylated PCP pincer palladium complex

The perfluoroalkylated pincer palladium complex promotes Heck reactions and can be recycled efficiently by fluorous solid-phase extraction without loss in catalytic activity.

Graphical abstract: A recyclable perfluoroalkylated PCP pincer palladium complex
From the themed collection: Fluorine Chemistry
Paper

Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: a counterpoise between weak intermolecular interactions and molecular symmetry

The directing capability of interactions involving ‘organic’ fluorine in aryl biscarbonates and an aryl biscarbamate as a function of acetylenic spacer units has been analyzed to authenticate the influence of such interactions on the conformational features.

Graphical abstract: Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: a counterpoise between weak intermolecular interactions and molecular symmetry
From the themed collection: Fluorine Chemistry
Paper

Synthesis of gold(I) fluoroalkyl and fluoroalkenyl-substituted phosphine complexes and factors affecting their crystal packing

From the solid state structures of a series of [AuCl(PR2Rf)] complexes (Rf = CF[double bond, length as m-dash]CF2, CF[double bond, length as m-dash]CFH, CCl[double bond, length as m-dash]CF2, C[triple bond, length as m-dash]CCF3, CF3, i-C3F7, s-C4F9) the relative importance of Au⋯F, hydrogen bonding, fluorous and aurophilic bonding interactions can be assessed.

Graphical abstract: Synthesis of gold(i) fluoroalkyl and fluoroalkenyl-substituted phosphine complexes and factors affecting their crystal packing
From the themed collection: Fluorine Chemistry
Paper

Synthesis of difluoroaryldioxoles using BrF3

The general pathway for a new synthesis of difluoroaryldioxoles.

Graphical abstract: Synthesis of difluoroaryldioxoles using BrF3
From the themed collection: Fluorine Chemistry
Paper

Enantiospecific synthesis of 2-[18F]fluoro-L-phenylalanine and 2-[18F]fluoro-L-tyrosine by isotopic exchange

2-[18F]Fluoro-L-phenylalanine and 2-[18F]fluoro-L-tyrosine were synthesized by isotopic exchange on corresponding precursors, followed by removal of the formyl group with Rh(PPh3)3Cl and subsequent hydrolysis of the protecting groups.

Graphical abstract: Enantiospecific synthesis of 2-[18F]fluoro-l-phenylalanine and 2-[18F]fluoro-l-tyrosine by isotopic exchange
From the themed collection: Fluorine Chemistry
Paper

SN2 Fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering

Ionic liquid is demonstrated to be a tailor-made solvent system for specific chemical reactions.

Graphical abstract: SN2 Fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering
From the themed collection: Fluorine Chemistry
Paper

Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation

Unprecedented fluorinated cyclohexane and aromatic derivatives were achieved from pentafluoropropiophenone via its tetrafluoroenol silyl ether and a stepwise Robinson annulation.

Graphical abstract: Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation
From the themed collection: Fluorine Chemistry
Paper

Chemical reactions inside structured nano-environment: SN2 vs. E2 reactions for the F + CH3CH2Cl system

A new transition state receptor for selective nucleophilic fluorination has been designed.

Graphical abstract: Chemical reactions inside structured nano-environment: SN2 vs. E2 reactions for the F− + CH3CH2Cl system
From the themed collection: Fluorine Chemistry
Paper

Synthesis and structural characterization of group 6 transition metal complexes with terminal fluoromethylidyne (CF) ligands; a DFT/NBO/NRT comparison of bonding characteristics of terminal NO, CF and CH ligands

Not enough pi to go around! Does the “triple bond” in fluoromethylidyne complexes really have a bond order of three?

Graphical abstract: Synthesis and structural characterization of group 6 transition metal complexes with terminal fluoromethylidyne (CF) ligands; a DFT/NBO/NRT comparison of bonding characteristics of terminal NO, CF and CH ligands
From the themed collection: Fluorine Chemistry
Paper

Fluoride ion donor properties of group 13 trifluorides (MF3, M = Al, Ga, In, Tl) and crystal structures of InF3·3SbF5, TlF3·3SbF5 and TlF3·AsF5·2HF

In the crystal structure of InF3·3SbF5 fluorine atoms bridge In and Sb metals (In–Fb–Sb) with very long Sb–Fb bonds, comparable with that in solid SbF5 (Sb–Fb–Sb).

Graphical abstract: Fluoride ion donor properties of group 13 trifluorides (MF3, M = Al, Ga, In, Tl) and crystal structures of InF3·3SbF5, TlF3·3SbF5 and TlF3·AsF5·2HF
From the themed collection: Fluorine Chemistry
Paper

Stabilisation of iridium(III) fluoride complexes with NHCs

No examples of fluoride-trans-NHC arrangements have been observed in a series of the new iridium(III) complexes [IrClF2(NHC)(COD)], [IrClF2(CO)2(NHC)] [IrF2L(NHC)(COD)][BF4] and [IrF2L(CO)2(NHC)][BF4].

Graphical abstract: Stabilisation of iridium(iii) fluoride complexes with NHCs
From the themed collection: Fluorine Chemistry
Paper

Taking TiF4 complexes to extremes - the first examples with phosphine co-ligands

Structural and spectroscopic characterisation of alkyldiphosphine complexes of TiF4 are reported, but arylphosphines, arsines and thioethers fail to form similar complexes, although [LigandH2][Ti4F18] were minor by-products for some soft-donor ligands.

Graphical abstract: Taking TiF4 complexes to extremes - the first examples with phosphine co-ligands
From the themed collection: Fluorine Chemistry
Paper

Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine

Treatment of trans-[Pd(F)(4-C5NF4)(PiPr3)2] with HBpin yields trans-[Pd(H)(4-C5NF4)(PiPr3)2]. Heating a solution of the latter to 60 °C in the presence of pentafluoropyridine affords 2,3,5,6-tetrafluoropyridine and the C–F activation product trans-[Pd(F)(4-C5NF4)(PiPr3)2].

Graphical abstract: Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine
From the themed collection: Fluorine Chemistry
26 items

About this collection

The RSC Fluorine Interest group celebrates its tenth anniversary. To commemorate this, the RSC has published a web themed issue on fluorine chemistry across several journals. For an introduction to this web themed issue by the Chair of the RSC Fluorine Chemistry Group and Guest Editor of this issue See OBC Blog.

Spotlight

Advertisements