Fonctionnalisation des iodures de F-alkyl-2 ethane par catalyse transfert de phase : importance de cette technique en serie F-alkylee

Szönyi, F.; Cambon, A.

doi:10.1016/s0022-1139(00)83967-6

Cited by 56 publications

(13 citation statements)

References 12 publications

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“…We decided to introduce sulfur and, thus, synthesize a homologous series of semifluorinated thioethers. Although there are some reports in the scientific literature regarding the synthesis of such compounds, [16][17][18] their physicochemical characterization has not been performed. Hydrogenated surfactants possessing thioether sulfur in the hydrophobic chain have also been studied.…”

Section: Introductionmentioning

confidence: 99%

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

et al. 2010

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A series of partially fluorinated aliphatic thioethers of the following formula: CF(3)-(CF(2))(7)-(CH(2))(10)-S-C(n)H(2n+1), where n = 1, 2, 4, 8, 12, and 18, were synthesized and spread from chloroform solution onto the water/air interface in a Langmuir trough. Upon compression of the film, the surface pressure-mean molecular area isotherms were recorded. It turned out that all the investigated compounds are capable of stable Langmuir monolayers formation. The electrical properties of the studied monolayers have been investigated by monitoring the change in the surface potential (ΔV) upon film compression. The performed experiments proved that regardless of the length of the C(n)H(2n+1) chain, the orientation of the film molecules is very similar. The investigated monolayers have been visualized applying Brewster angle microscopy. The monolayers of the shorter homologues turned out to be homogeneous until their collapse, whereas for longer homologues, the formation of multilayer aggregates was observed. The methods of grazing incidence X-ray diffraction (GIXD) and X-ray reflectivity (XR) have also been applied for the characterization of the organization of thioether molecules in their monolayers. The GIXD experiments proved that the films of the studied thioethers possess a periodical in-plane structure. They are collectively tilted toward the next neighbor (NN tilt), and their packing within the monolayer (xy) plane can be described by the 2-dimentional rectangular centered lattice. Interpretation of the XR results indicate that only the partially fluorinated chain of the thioether molecule is periodically organized at the water/air interface, whereas the hydrocarbon chain is disordered and has a liquid character.

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Section: Introductionmentioning

confidence: 99%

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

et al. 2010

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“…The triazole‐based imidazolium salts 4a – c , each bearing one fluorous ponytail, were prepared by the copper‐catalysed Huisgen cycloaddition of the corresponding imidazolium salts 2a – c with the fluorous azide 3 16 in the presence of diisopropylamine (DIPA) in 2,2,2‐trifluoroethanol (Scheme ) 17…”

Section: Resultsmentioning

confidence: 99%

Functionalisable N‐Heterocyclic Carbene–Triazole Palladium Complexes and Their Application in the Suzuki–Miyaura Reaction

et al. 2014

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Seven functionalised N-heterocyclic carbene (NHC) ligands and their corresponding palladium(II) complexes have been synthesised with a triazole moiety as a modular and stable linkage between the catalytic centre and the secondary functional group. The complexes were prepared in good yields and fully characterised by NMR spectroscopy, mass spec- [a]2088 trometry and X-ray crystallography. The complexes are active in the Suzuki-Miyaura cross-coupling reaction, with catalytic activities maintained whatever the triazolyl substituent. This opens the possibility for various functionalisations of NHC-palladium complexes.

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“…[6d] and chloride/ azide exchange of 8 [12] followed by the CuAAC of the resulting 9 and 10 proceeded with high yields to give rise to the monotagged azabis(oxazoline) ligand 11. Likewise, ligation of 9 with azide 12 [13] furnished the azabis(oxazoline) 13, having three perfluoroalkyl chains and four triazoles incorporated (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Combining Fluorous and Triazole Moieties for the Tagging of Chiral Azabis(oxazoline) Ligands

Rasappan¹,

Olbrich²,

Reiser³

2009

Adv Synth Catal

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New fluorous-tagged azabis(oxazoline) ligands were prepared using the copper-catalyzed azide-alkyne cycloaddition as ligation method. The resulting ligands were tested in copper-catalyzed asymmetric benzoylations (up to 99% ee), nitroaldol (up to 90% ee), and Michael reactions (up to 82% ee). The combination of unpolar fluorinated alkyl chains and polar triazole moieties imposes properties that are beneficial for the catalysts with respect to recyclability and selectivity. The scope and limitation of this strategy in comparison to analogous catalysts immobilized on methoxypolyethylene glycol (MeOPEG) or polystyrene is discussed. Moreover, this study shows that the choice of solvent for a given reaction is crucial to arrive at highly recyclable bis(oxazoline) catalysts.

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Fonctionnalisation des iodures de F-alkyl-2 ethane par catalyse transfert de phase : importance de cette technique en serie F-alkylee

Cited by 56 publications

References 12 publications

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

Functionalisable N‐Heterocyclic Carbene–Triazole Palladium Complexes and Their Application in the Suzuki–Miyaura Reaction

Combining Fluorous and Triazole Moieties for the Tagging of Chiral Azabis(oxazoline) Ligands

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