Category: 1206-46-8

Luo, Jinyun published the artcileThe organocatalytic synthesis of perfluorophenylsulfides via the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates, Quality Control of 1206-46-8, the publication is Organic & Biomolecular Chemistry (2021), 19(42), 9237-9241, database is CAplus and MEDLINE.

The organic superbase t-Bu-P₄-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P₄ were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl-sulfur bond under mild metal-free reaction conditions.

Organic & Biomolecular Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Quality Control of 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Frohn, H.-J. published the artcileReactions of methyl(pentafluorophenyl)- and methyl(pentafluorophenyl)phenylsilanes with electrophiles. A convenient preparative route to halo(methyl)pentafluorophenylsilanes C₆F₅SiMe₂X and C₆F₅SiMeX₂ (X = F, Cl and Br), Application In Synthesis of 1206-46-8, the publication is Journal of Organometallic Chemistry (1998), 570(2), 255-263, database is CAplus.

Halo(methyl)pentafluorophenylsilanes C₆F₅SiMe_nX_3-n (n = 1, 2) (X = F, Cl, Br) were prepared in good yields from the corresponding phenylsilanes C₆F₅SiMe_nPh_3-n by reactions with the electrophiles anhydrous HF, HCl-AlCl₃, Br₂-AlBr₃ or AlX₃ (X = Cl, Br) in halogenated hydrocarbons. Addnl., reactions of C₆F₅SiMe₃ and (C₆F₅)₂SiMe₂ with selected electrophiles were studied.

Journal of Organometallic Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Application In Synthesis of 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zemtsov, Artem A. published the artcileReactions of fluorinated silanes with 2-nitrocinnamates, Recommanded Product: Trimethyl(perfluorophenyl)silane, the publication is Journal of Fluorine Chemistry (2011), 132(6), 378-381, database is CAplus.

The interaction of ¦Á-nitrocinnamates with Me₃SiR_f (R_f = CF₃, C₂F₅, C₆F₅) promoted by NaOAc in DMF or by Bu₄NOAc in CH₂Cl₂ was described. The reactions proceeded as conjugate addition of the resp. fluorinated carbanion at the C:C bond and afforded 3-aryl-2-nitrobutanoic acid Me esters (aryl = Ph, 4-MeOC₆H₄, 2-furyl) bearing a fluorinated substituent in good yields as diastereomeric mixtures in ratios of 1:1 to 1.6:1. Subsequent hydrogenation led to amino acid esters.

Journal of Fluorine Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9NO6S, Recommanded Product: Trimethyl(perfluorophenyl)silane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zemtsov, Artem A. published the artcileReaction of Baylis-Hillman Adducts with Fluorinated Silanes, Application of Trimethyl(perfluorophenyl)silane, the publication is European Journal of Organic Chemistry (2010), 6779-6785, S6779/1-S6779/7, database is CAplus.

Reactions of acylated Baylis-Hillman adducts bearing nitrile, ester, or ketone groups with C₆F₅-substituted silicon reagents Me_nSi(C₆F₅)_4-n (n = 1-3) have been studied. The reactions are initiated by Bu₄NOAc (5 mol-%) in MeCN or DMF under mild conditions and afford products of allylic substitution of the acetoxy group by the C₆F₅ carbanion in good yields. Predominant or exclusive formation of one geometrical isomer was observed in all cases (Z for nitriles, E for esters and ketones). For substrates containing carbonyl groups, nucleophilic attack of the C₆F₅ carbanion chemoselectively occurred at the C=C bond. Reactions of acylated Baylis-Hillman adducts with Me₃SiCF₃ were found to be inefficient, as the CF₃ carbanion had the propensity to attack the C=O bond of substrates with ester or ketone substituents.

European Journal of Organic Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C14H28O5S, Application of Trimethyl(perfluorophenyl)silane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Dilman, Alexander D. published the artcileNucleophilic trifluoromethylation of arylidenemalononitriles, COA of Formula: C9H9F5Si, the publication is Tetrahedron Letters (2008), 49(28), 4352-4354, database is CAplus.

A method for the nucleophilic trifluoromethylation of arylidenemalononitriles using Me₃SiCF₃ is described. The reaction is carried out in DMF in the presence of AcONa as a Lewis base, and affords Michael addition products in high yield.

Tetrahedron Letters published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, COA of Formula: C9H9F5Si.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Dilman, Alexander D. published the artcileSynthesis of C₆F₅-substituted amines containing quaternary carbon atoms, Synthetic Route of 1206-46-8, the publication is Synthesis (2006), 447-450, database is CAplus.

The reaction of enamines and methyltris(pentafluorophenyl)silane in the presence of acetic acid affording C₆F₅-substituted amines is described. The proposed mechanism features a transfer of the C₆F₅ group from the five-coordinate silicate intermediate onto an iminium cation resulting in the generation of a quaternary carbon atom in the C-C bond forming event.

Synthesis published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Synthetic Route of 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Nagase, Masahiro published the artcile4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds, Computed Properties of 1206-46-8, the publication is Journal of the American Chemical Society (2016), 138(19), 6103-6106, database is CAplus and MEDLINE.

The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded in good yield, even in gram scale, and by a sequential reaction without isolating the intermediates. This reaction could be applied to late-stage trifluoromethylation of a bioactive compound

Journal of the American Chemical Society published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Computed Properties of 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Levin, Vitalij V. published the artcileNucleophilic fluoroalkylation of iminium salts, Quality Control of 1206-46-8, the publication is Tetrahedron Letters (2008), 49(19), 3108-3111, database is CAplus.

Iminium cations generated by the coupling of aldehydes, N-trimethylsilylamines and TMSOTf or by the methylation of imines with MeOTf smoothly react with silanes of a general formula Me₃SiR_f (R _f = CF₃, CCl₂F, C₆F₅) to afford the corresponding tertiary amines having a fluorinated substituent. The key step, involving C-C bond formation, is promoted by NaOAc or KF in DMF as a solvent.

Tetrahedron Letters published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Quality Control of 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Huang, Dejian published the artcileFacile and Reversible Cleavage of C-F Bonds. Contrasting Thermodynamic Selectivity for Ru-CF₂H vs F-Os:CFH, Application of Trimethyl(perfluorophenyl)silane, the publication is Journal of the American Chemical Society (2000), 122(37), 8916-8931, database is CAplus.

In the presence of a catalytic amount of F^– (CsF), Me₃SiR_f (R_f = CF₃ and C₆F₅) exchanges R_f with fluoride of the 16-electron complexes MHF(CO)L₂ (M = Ru, Os; L = PⁱPr₃, P^tBu₂Me) to give Me₃Si-F and the unsaturated pentafluorophenyl complexes, MH(C₆F₅)(CO)L₂, or (when R_f = CF₃) saturated fluorocarbene complexes, MHF(CF₂)(CO)L₂, via ¦Á-F migration. X-ray crystal structure and solution ¹⁹F NMR studies reveal that, in the ground state, the three atoms of the CF₂ group lie in a plane perpendicular to the P-Ru-P axis so that the ¦Ð-back-donation is maximized and the carbene substituents are inequivalent. Having hydride trans to the CF₂ ligand, MHF(CF₂)(CO)L₂ is a kinetic product, which converts to a thermodn. isomer. For Ru, the final product is a 16e complex, RuF(CF₂H)(CO)L₂, formed by combination of CF₂ and hydride. For Os, the product is an 18e complex, OsF₂(:CFH)(CO)L₂, resulting from exchange of one carbene fluoride with the hydride. The distinct difference between Os and Ru demonstrates the principle that 3rd-row transition metals show a pronounced tendency toward a higher oxidation state. The isomerization mechanism involves phosphine dissociation as a slow step. Coordinatively saturated RuHF(CF₂)(CO)L₂ reacts with CO within the time of mixing to give the F and CF₂ recombination product, RuH(CF₃)(CO)₂L₂. This unexpectedly fast carbonylation reaction, as well as ¹⁹F spin saturation transfer experiments, reveals the existence of a fast ¦Á-F migration equilibrium between RuHF(CF₂)(CO)L₂ and RuH(CF₃)(CO)L₂ in solution In sharp contrast, the Os analog does not have such a fast equilibrium, and therefore it does not react with CO at room temperature At higher temperature, reaction occurs forming the hydride and fluoride exchanged product, Os(CHF₂)(F)(CO)₂L₂. The contrasting behavior of Ru vs. Os regarding stability of fluoroalkyl and fluorocarbene is discussed on the basis of the theor. calculations, which also provide insight into the isomerization of RuHF(CF₂)(CO)L₂. Hydrogenolysis of Ru(CF₂H)F(CO)L₂ liberates CH₂F₂, forming RuHF(CO)L₂.

Journal of the American Chemical Society published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Application of Trimethyl(perfluorophenyl)silane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Frohn, H. J. published the artcileReactions of pentafluorophenylxenon(II) hexafluoroarsenate [C₆F₅Xe]⁺[AsF₆]^– with aromatic compounds, Name: Trimethyl(perfluorophenyl)silane, the publication is Journal of Fluorine Chemistry (1993), 64(3), 201-15, database is CAplus.

Pentafluorophenylxenon(II) hexafluoroarsenate, [C₆F₅Xe]⁺[AsF₆]^–, reacts (MeCN, 20¡ã) with aromatic compounds C₆H₅X (X = Me, F, CF₃, NO₂ and CN), yielding isomeric mixtures of polyfluorinated biphenyls XC₆H₄C₆F₅. When X = I, iodopentafluorobenzene is also formed, whereas trimethylsilylbenzene (X = SiMe₃) is only converted to C₆H₅C₆F₅ and C₆F₅H. These results are compared with the data for radical pentafluorophenylation and for fluorination reactions of the corresponding aromatic compounds with XeF₂. Polyfluoroarom. compounds C₆F₆, C₆F₅H, C₆F₅I, C₆F₅CN and C₆F₅SiMe₃ do not react with [C₆F₅Xe]⁺[AsF₆]^– under the same conditions.

Journal of Fluorine Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Name: Trimethyl(perfluorophenyl)silane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia