Category: 1206-46-8

Panne, Patricia published the artcileCyanide initiated perfluoroorganylations with perfluoroorgano silicon compounds, Name: Trimethyl(perfluorophenyl)silane, the publication is Journal of Fluorine Chemistry (2001), 112(2), 283-286, database is CAplus.

Cyanophenylphosphines, Ph₂PCN or PhP(CN)₂, do not react with Me₃SiCF₃ or Me₃SiC₆F₅ in the absence of cyanide ions. Catalytic amounts of ionic cyanides such as [NEt₄]CN, [18-crown-6-K]CN or NaCN initiate perfluoroorganylation reactions. The trifluoromethylphosphines, Ph₂PCF₃ and PhP(CF₃)₂, as well as the pentafluorophenylphosphines, Ph₂PC₆F₅ and PhP(C₆F₅)₂, are isolated in 60-75% yield. In DMF or acetone solutions, side reactions are observed while reactions in CH₂Cl₂ and MeCN proceed selectively. Me₃SiCF₃ addition to the carbonyl groups of DMF and acetone occurs on treatment of Me₃SiCF₃ solutions of these solvents with catalytic amounts of cyanide, cyanate or thiocyanate salts even at low temperature The formation of the reactive silicate [Me₃Si(CN)CF₃]^– in reactions with an excess of [18-crown-6-K]CN is proved by low temperature NMR studies.

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

Maggiarosa, Nicola published the artcileBis(pentafluorophenyl)xenon, Xe(C₆F₅)₂: a homoleptic diorganoxenon derivative, Name: Trimethyl(perfluorophenyl)silane, the publication is Angewandte Chemie, International Edition (2000), 39(24), 4588-4591, database is CAplus and MEDLINE.

Reaction of Me₃SiC₆F₅/[Me₄N]F with XeF₂ in propionitrile, propionitrile/acetonitrile, acetonitrile, or CH₂Cl₂ gave Xe(C₆F₅)₂, the first [10-Xe-2] with two xenon-carbon bond. When the same reaction was carried in 1:1 stoichiometry, C₆F₅XeF was formed predominantly. Reaction of C₆F₅XeF with Me₃SiOSO₂CF₃ gave [C₆F₅Xe]⁺OSO₂CF₃.

Angewandte Chemie, International Edition 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

Kremlev, Mikhail M. published the artcileApproaches to prepare perfluoroalkyl and pentafluorophenyl copper couples for cross-coupling reactions with organohalogen compounds, Product Details of C9H9F5Si, the publication is Dalton Transactions (2015), 44(45), 19693-19699, database is CAplus and MEDLINE.

The reactions of iodoperfluoroalkanes C_nF_2n+1I (n = 2, 3, 4) and BuLi at low temperatures give NMR spectroscopic evidence for LiC_nF_2n+1 which were converted into LiCu(C_nF_2n+1)₂ derivatives upon treatment with 0.5 mol Cu(I) bromide, CuBr. An alternative route to obtain perfluoroorgano Cu couples, Cu(R_f)₂Ag (R_f = n-C₃F₇, n-C₄F₉, C₆F₅) was achieved from the reactions of the corresponding perfluoroorgano Ag(I) reagents, AgR_f, and elemental Cu through redox transmetallations. The composition of the resulting reactive intermediates was studied by ¹⁹F NMR spectroscopy and ESI mass spectrometry. Perfluoro-Pr and perfluoro-Bu Cu-Ag reagents prepared by the oxidative transmetalation route exhibited good properties in C-C bond formation reactions with acid chlorides even under moderate conditions. Substitution of Br directly bound to aromatics for perfluoroalkyl groups was achieved at elevated temperatures, while success in halide substitution reactions using Li Cu couples remained poor.

Dalton Transactions 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, Product Details of C9H9F5Si.

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

Dilman, A. D. published the artcileTrifluoromethylation and pentafluorophenylation of enamines, Recommanded Product: Trimethyl(perfluorophenyl)silane, the publication is Russian Chemical Bulletin (2007), 56(8), 1522-1525, database is CAplus.

Reaction of enamines, e.g., I, with Me₃SiCF₃ and Me₃SiC₆F₅ in the presence of carboxylic acids leading to ¦Á-CF₃– and ¦Á-C₆F₅-substituted amines, e.g., II, has been studied. 3-Cyanobenzoic acid was found to be the optimal promoter of these reactions.

Russian Chemical Bulletin 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, Recommanded Product: Trimethyl(perfluorophenyl)silane.

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

Nishida, Masakazu published the artcileReactions of Highly Branched Perfluoroolefins with (Pentafluorophenyl)trimethylsilane: Characterization of the Unique Structural Properties of Perfluorinated Super-Congested Systems, Computed Properties of 1206-46-8, the publication is Asian Journal of Organic Chemistry (2016), 5(7), 927-937, database is CAplus.

Hexafluoropropene trimers were reacted with C₆F₅Si(CH₃)₃ to provide not only pentafluorophenyl but also perfluorophenylene derivatives [F(C₆F₄)_nC₉F₁₇; n = 2-9] by successive pentafluorophenylation of perfluoroaryl rings. Their structures, including rotational isomers, were determined by MS, ¹⁹F and ¹³C-{¹⁹F} NMR spectroscopy, and/or X-ray crystallog. and were further confirmed by B3LYP-GIAO calculation of NMR shieldings. Formation of a pair of gear-meshed rotamers with clockwise and counterclockwise conformations was identified by NMR measurements for the structures having geminal (CF₃)₂CF groups at the C=C bond. That the predominantly formed counterclockwise rotamer was gradually converted to the clockwise rotamer over 50 days at room temperature through a synchronized movement of gears was also confirmed by NMR measurements. A comparison between the X-ray structure and B3LYP calculations showed some structural differences that arise from the crystal packing.

Asian 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 C9H9F5Si, Computed Properties of 1206-46-8.

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

Iwasaki, Takanori published the artcileMulticomponent Coupling Reaction of Perfluoroarenes with 1,3-Butadiene and Aryl Grignard Reagents Promoted by an Anionic Ni(II) Complex, Product Details of C9H9F5Si, the publication is Organic Letters (2016), 18(19), 4868-4871, database is CAplus and MEDLINE.

In the presence of in situ-generated anionic nickel catalysts, aryl Grignard reagents such as 4-fluorophenylmagnesium bromide, 1,3-butadiene, and perfluoroarenes such as perfluorobenzene underwent diastereoselective and chemoselective three-component coupling reactions to yield (aryl)(perfluoroaryl)octadienes such as I. A thermally unstable anionic nickel complex II?Li(12-crown-4)₂⁺ was prepared from PhLi, 1,3-butadiene, Ni(cod)₂, and 12-crown-4 and its crystal structure determined and used as a catalyst for the three-component coupling reaction.

Organic 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, Product Details of C9H9F5Si.

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

Nishimine, Takayuki published the artcileKinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted C-F Bond Cleavage, Synthetic Route of 1206-46-8, the publication is Angewandte Chemie, International Edition (2014), 53(2), 517-520, database is CAplus and MEDLINE.

Under optimized reaction conditions, the synthesis of the target compounds was achieved by a reaction of trimethyl(trifluoromethyl)silane with Morita-Baylis-Hillman-reaction products [¦Â-fluoro-¦Á-(methylene)benzenepropanoic acid ester derivatives] using (9S)-(9”S)-9,9”-[1,4-phthalazinediylbis(oxy)]bis[10,11-dihydro-6′-methoxycinchonan] [i.e., (DHQD)₂PHAL] as catalyst. The products thus formed included (¦ÂS)-¦Á-methylene-¦Â-(trifluoromethyl)benzenepropanoic acid Me ester (I), (¦ÂR)-¦Á-methylene-¦Â-(trifluoromethyl)benzenepropanoic acid Me ester and (¦ÂR)-¦Â-fluoro-¦Á-(methylene)benzenepropanoic acid Me ester, (¦ÂS)-¦Â-fluoro-¦Á-(methylene)benzenepropanoic acid Me ester. The corresponding enantiomers were obtained using (9S,9”S)-9,9”-[(2,5-diphenyl-4,6-pyrimidinediyl)bis(oxy)]bis[10,11-dihydro-6′-methoxycinchonan] [(DHQD)₂PYR] as catalyst.

Angewandte Chemie, International Edition 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

Nishida, Masakazu published the artcileMultiple pentafluorophenylation of 2,2,3,3,5,6,6-heptafluoro-3,6-dihydro-2H-1,4-oxazine with an organosilicon reagent: NMR and DFT structural analysis of oligo(perfluoroaryl) compounds, Recommanded Product: Trimethyl(perfluorophenyl)silane, the publication is Helvetica Chimica Acta (2006), 89(11), 2671-2685, database is CAplus.

The reagent Me₃Si(C₆F₅) was used for the preparation of a series of perfluorinated, pentafluorophenyl-substituted 3,6-dihydro-2H-1,4-oxazines (2-8), which, otherwise, would be very difficult to synthesize. Multiple pentafluorophenylation occurred not only on the heterocyclic ring of the starting compound 1 (Scheme), but also in para position of the introduced C₆F₅ substituent(s) leading to compounds with one to three nonafluorobiphenyl (C₁₂F₉) substituents. While the tris(pentafluorophenyl)-substituted compound 3 could be isolated as the sole product by stoichiometric control of the reagent, the higher-substituted compounds 5-8 could only be obtained as mixtures The structures of the oligo(perfluoroaryl) compounds were confirmed by ¹⁹F- and ¹³C-NMR, MS, and/or X-ray crystallog. DFT simulations of the ¹⁹F- and ¹³C-NMR chem. shifts were performed at the B3LYP-GIAO/6-31++G(d,p) level for geometries optimized by the B3LYP/6-31G(d) level, a technique that proved to be very useful to accomplish full NMR assignment of these complex products.

Helvetica Chimica Acta 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, Recommanded Product: Trimethyl(perfluorophenyl)silane.

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

Abo-Amer, Anwar published the artcileFrom hypervalent xenon difluoride and aryliodine(III) difluorides to onium salts: Scope and limitation of acidic fluoroorganic reagents in the synthesis of fluoroorgano xenon(II) and iodine(III) onium salts, Quality Control of 1206-46-8, the publication is Journal of Fluorine Chemistry (2006), 127(10), 1311-1323, database is CAplus.

Fluorinated organodifluoroboranes R_fBF₂ (R_f = fluorinated alkyl, aryl) are in general suitable reagents to transform XeF₂ and RIF₂ (R = alkyl, aryl) into the corresponding onium tetrafluoroborate salts [R_fXe][BF₄] and [R(R_f)I][BF₄], resp. (4-C₅F₄N)BF₂ (C₅F₄N = tetrafluoropyridyl) and trans-CF₃CF:CFBF₂ which represent boranes of high acidity form no Xe-C onium salts in reactions with XeF₂ but give the desired iodonium salts with RIF₂ (R = C₆F₅, o-, m-, p-C₆FH₄). The reaction of (4-C₅F₄N)BF₂ with XeF₂ ends with a XeF₂-borane adduct. The solid product is shock sensitive. Furthermore cooled (¡Ü -60 ¡ãC) samples in FEP tubes exploded several times during the alignment in the Raman spectrometer. C₆F₅Xe(4-C₅F₄N), the 1st Xe-(4-C₅F₄N) compound, was obtained when C₆F₅XeF was reacted with Cd(4-C₅F₄N)₂. (4-C₅F₄N)IF₂ was prepared in 84% yield from XeF₂ and (4-C₅F₄N)I. Reactions of (4-C₅F₄N)IF₂ and C₆F₅IF₂ with (4-C₅F₄N)BF₂ gave [(4-C₅F₄N)₂I][BF₄] and [C₆F₅(4-C₅F₄N)I][BF₄] in 88% and quant. yields, resp. Analogously, aryl(perfluoroalkenyl)iodonium salts [R(R’)I][BF₄] (R = C₆F₅, o-, m-, p-C₆FH₄, R’ = trans-CF₃CF:CF, CF₂:CF) were obtained from RIF₂ and R’BF₂ in 75% to 94% yields. The gas phase fluoride affinities pF^– of selected fluoroorganodifluoroboranes R_fBF₂ and their hydrocarbon analogs were calculated (B3LYP/6-31+G^*) and discussed with respect to their potential to introduce R_f-groups into hypervalent EF₂ (E = Xe, RI; R = organic group) bonds. Four aspects which influence the transformation of hypervalent EF₂ bonds under the action of Lewis acidic reagents RAF_n-1 (A = B, P; n = 3, 5) into the corresponding [RE][AF_n+1] salts are presented and the important role of the acidity is emphasized. Fluoride affinities may help to plan the introduction of organo groups into EF₂ moieties and to expand the types of acidic reagents. Thus C₆H₅PF₄ with a pF^– value comparable to that of R_fBF₂ compounds is able to introduce the Ph group into RIF₂ (R = C₆F₅ (94% yield), p-C₆FH₄ (93%)).

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, Quality Control of 1206-46-8.

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

Breuer, W. published the artcileChemistry of bromine pentafluoride. 3. Reactions of bromine pentafluoride and arylbromine tetrafluoride with N-bases, of arylbromine tetrafluoride with fluoride ions, and the fluorine-aryl monosubstitution reactions on the hexafluorobromate(V) anion, Name: Trimethyl(perfluorophenyl)silane, the publication is Zeitschrift fuer Anorganische und Allgemeine Chemie (1992), 85-91, database is CAplus.

BrF₅ forms 1:1 adducts with pyridines in organic solvents. In BrF₅-N-base adducts the axial Br-F bond is activated for F-aryl substitution reactions. Arylbromine tetrafluorides resulting from F-aryl monosubstitutions also yield 1:1 adducts with pyridines; in contrast to BrF₅ they react with F^– under reductive elimination. F-aryl substitutions on [BrF₆]^– are presented and the influence of the Lewis-acidity of the aryl transfer reagent and its coproduct is discussed.

Zeitschrift fuer Anorganische und Allgemeine Chemie 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