Category: 107263-95-6

Kiselyov, Alexander S. published the artcileA novel three-component reaction of N-fluoropyridinium salts: a facile approach to imidazo[1,2-a]pyridines, Formula: C6H5F4NO3S, the publication is Tetrahedron Letters (2005), 46(26), 4487-4490, database is CAplus.

The reaction of N-fluoropyridinium triflates I (R¹ = H, 2-Me, 4-Me₂CH, 2-Ph, 3-Cl, etc.) with isonitriles R²NC (R² = Me₂CH, Me₃C, EtO₂CH₂, cyclohexyl, Ph, PhCH₂, etc.) in acetonitrile or propionitrile in the presence of NaBH(OAc)₃ led to the formation of the corresponding imidazo[1,2-a]pyridines II (R³ = Me, Et) in 44-73% yields. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species and apparent reduction of the pyridinium intermediate with NaBH(OAc)₃ to yield the targeted heterocycles.

Tetrahedron Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Formula: C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Liao, Lihao published the artcileSelenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles, Application In Synthesis of 107263-95-6, the publication is ACS Catalysis (2018), 8(7), 6745-6750, database is CAplus.

In the presence of di-Ph diselenide, N-fluoropyridinium triflates, and water, propargyl phosphonates such as PhCCCH₂P(:O)(OEt)₂ and β,γ-alkynoates underwent regioselective oxidation to yield γ-ketoalkynyl phosphonates such as PhCOCCP(:O)(OEt)₂ and γ-keto-α,β-alkynoates. Ynamides such as PhCCN(CH₂Ph)R (R = MeSO₂, PhSO₂, 4-MeC₆H₄SO₂, 4-O₂NC₆H₄) underwent regioselective oxidative cycloadditions with acetonitrile or butanenitrile mediated by Selectfluor in the presence of di-Ph selenide to yield aminooxazoles such as I (R = MeSO₂, PhSO₂, 4-MeC₆H₄SO₂, 4-O₂NC₆H₄). N-Propargylamides underwent oxidative cyclization in the presence of di-Ph diselenide and mediated by Selectfluor to give 2-substituted-5-oxazolecarboxaldehydes. In all cases, the reactions are likely to involve the reactions of cationic phenylselenium species with alkynes to generate vinylselenium cations. The mechanism of the reactions were studied; vinyl selenides were prepared by reactions of phenylselenium triflate with propargyl phosphonates and ynamides and shown to yield the observed ketone and oxazole products upon elimination, while isotopic labeling experiments were undertaken to determine the fate of added water.

ACS Catalysis published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Liu, Xuemei published the artcileEffect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin, Application In Synthesis of 107263-95-6, the publication is Chemical Research in Toxicology (2003), 16(6), 741-749, database is CAplus and MEDLINE.

Estrogen replacement therapy has been correlated with an increased risk for developing breast and endometrial cancers. One potential mechanism of estrogen carcinogenesis involves metabolism of estrogens to 2- and 4-hydroxylated catechols, which are further oxidized to electrophilic/redox active o-quinones that have the potential to both initiate and promote the carcinogenic process. Previously, the authors showed that the equine estrogens, equilin and equilenin, which are major components of the estrogen replacement formulation Premarin (Wyeth-Ayerst), are primarily metabolized to the catechol, 4-hydroxyequilenin. This catechol was found to autoxidize to an o-quinone causing oxidation and alkylation of DNA in vitro and in vivo. To block catechol formation from equilenin, 4-halogenated equilenin derivatives were synthesized. These derivatives were tested for their ability to bind to the estrogen receptor, induce estrogen sensitive genes, and their potential to form catechol metabolites. The authors found that the 4-fluoro derivatives were more estrogenic than the 4-chloro and 4-bromo derivatives as demonstrated by a higher binding affinity for estrogen receptors α and β, an enhanced induction of alk. phosphatase activity in Ishikawa cells, pS2 expression in S30 cells, and PR expression in Ishikawa cells. Incubation of these compounds with tyrosinase in the presence of GSH showed that the halogenated equilenin compounds formed less catechol GSH conjugates than the parent compounds, equilenin and 17β-hydroxyequilenin. In addition, these halogenated compounds showed less cytotoxicity in the presence of tyrosinase than the parent compounds in S30 cells. Also, as stated above, the 4-fluoro derivatives showed similar estrogenic effects as compared with parent compounds; however, they were less toxic in S30 cells as compared to equilenin and 17β-equilenin. Because 17β-hydroxy-4-halogenated equilenin derivatives showed higher estrogenic effects than the halogenated equilenin derivatives in vitro, the authors studied the relative ability of the 17β-hydroxy-4-halogenated equilenin derivatives to induce estrogenic effects in the ovariectomized rat model. The 4-fluoro derivative showed higher activity than 4-chloro and 4-bromo derivatives as demonstrated by inducing higher vaginal cellular differentiation, uterine growth, and mammary gland branching. However, 17β-hydroxy-4-fluoroequilenin showed a lower estrogenic activity than 17β-hydroxyequilenin and estradiol, which could be due to alternative pharmacokinetic properties for these compounds These data suggest that the 4-fluoroequilenin derivatives have promise as alternatives to traditional estrogen replacement therapy due to their similar estrogenic properties with less overall toxicity.

Chemical Research in Toxicology published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Liu, Qilun published the artcileAbnormal Mesoionic Carbene Silver Complex: Synthesis, Reactivity, and Mechanistic Insight on Oxidative Fluorination, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is ACS Catalysis (2015), 5(11), 6732-6737, database is CAplus.

A silver-catalyzed intramol. amination of alkynyl-imine substrates has been extensively studied to build various isoquinoline derivatives efficiently. However, most of these transformations are limited to hydroamination, and the related oxidative reaction is quite rare. Importantly, the mechanistic details are still unknown, which retarded further progress in the field. In this work, a novel abnormal mesoionic carbene silver complex (MIC)_nAg(I) was isolated and fully characterized as the key intermediate. Further investigation on the oxidative transformation of the silver complex reveals that successful oxidative halogenation could be achieved with NXS (X = Cl, Br, and I), as well as F⁺ reagent. Surprisingly, the fluorination reaction occurred in the presence of both strong (SelectFluor) and weak (NFSI) fluorinating reagents, although the F-Py-type reagent, whose oxidative potential lies between, is ineffective. Further mechanistic studies disclosed that (1) from kinetic data, the (MIC)Ag(I) complex was proved to be the reactive intermediate in the fluorination reaction, and pyridyl-oxazoline (Pyox) ligand could significantly improve this transformation; (2) from DFT calculation results, two different mechanistic pathways were suggested to be involved, a metathesis process in the case of NFSI promoted by the chelation of sulfonyl group toward the silver center and a redox process in the case of SelectFluor due to its strong oxidative potential.

ACS Catalysis published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Recommanded Product: 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Baba, Daisuke published the artcileElectrolytic partial fluorination of organic compounds. Part 62. Highly diastereoselective anodic fluorination of chiral 1,3-oxathiolan-5-ones derived from camphorsulfonamides, Quality Control of 107263-95-6, the publication is Journal of Fluorine Chemistry (2003), 121(1), 93-96, database is CAplus.

Anodic fluorination of chiral 1,3-oxathiolan-5-ones, derived from camphorsulfonamide and thioglycolic acid, was carried out under various conditions. When dimethoxyethane (DME) containing Et₄NF·4HF was used, the corresponding monofluorinated products were obtained in good yield as a single diastereomer. Chem. fluorination was also attempted using N-fluoropyridinium salts; however, fluorination did not proceed at all. The anodic fluorination of (+)-(1R,2R,4R)-7,7-dimethyl-N,N-bis(1-methylethyl)-5′-oxo-spiro[bicyclo[2.2.1]heptane-2,2′-[1,3]oxathiolane]-1-methanesulfonamide gave (+)-(1R,2R,4R,4′S)-4′-Fluoro-7,7-dimethyl-N,N-bis(1-methylethyl)-5′-oxo-spiro[bicyclo[2.2.1]heptane-2,2′-[1,3]oxathiolane]-1-methanesulfonamide (I). Crystal and mol. structures of I were reported.

Journal of Fluorine Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Quality Control of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Lou, Shao-Jie published the artcilePd(OAc)₂-catalyzed regioselective aromatic C-H bond fluorination, Category: pyridine-derivatives, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(55), 6218-6220, database is CAplus and MEDLINE.

A novel Pd(OAc)₂-NFSI-TFA system was developed for the highly selective ortho-monofluorination directed by diverse aryl-N-heterocyclic directing groups e.g., quinoxaline, pyrazole, benzo[d]oxazole, and pyrazine derivatives A Pd(ii/iv) catalytic cycle was proposed based on the ESI-MS/MS studies.

Chemical Communications (Cambridge, United Kingdom) published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Pereira, Raul published the artcileSynthesis and characterization of a novel N-F reagent derived from the ethano-Tröger’s base: ¹J_FN coupling constants as a signature for the N-F bond, Application In Synthesis of 107263-95-6, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(8), 1606-1609, database is CAplus and MEDLINE.

Methylation of 2,8-dimethyl-6H,12H-5,11-ethanodibenzo[b,f][1,5]-diazocine (ethano-Troddoger’s base) with Me iodide followed by ion metathesis and fluorination with N-fluoro-2,3,4,5,6-pentachloropyridinium triflate affords a new electrophilic N-F reagent, that is more reactive than Selectfluor. 2D ¹⁹F-¹⁵N HMQC experiments provide ¹J_NF coupling constants which are diagnostic for the N-F functional group.

Chemical Communications (Cambridge, United Kingdom) published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Application In Synthesis of 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Chen, Changpeng published the artcilePalladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines, HPLC of Formula: 107263-95-6, the publication is Journal of Organic Chemistry (2015), 80(2), 942-949, database is CAplus and MEDLINE.

A novel and efficient synthetic method for o-fluorobenzylamines via palladium catalyst using an easily accessible oxalyl amide as directing group has been developed. The cheap N-fluorobenzenesulfonimide could be used as an effective [F⁺] source and t-amyl-OH as the solvent with Pd(OAc)₂ as catalyst. Selective mono- or difluorination of oxalyl amide-protected benzylamine derivatives were achieved by modifying the reaction conditions, which presented an efficient method for the preparation of ortho-fluorinated benzylamines.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, HPLC of Formula: 107263-95-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcileBase-initiated reactions of N-fluoropyridinium salts; a novel cyclic carbene proposed as a reactive species, Name: 1-Fluoropyridiniumtriflate, the publication is Tetrahedron Letters (1987), 28(24), 2705-8, database is CAplus.

Deprotonation of 1-fluoropyridinium triflate with Et₃N gave cyclic carbene I, which reacted with the solvent (e.g. CH₂Cl₂, CH₂Br₂, MeCN, C₆H₆, Me₂CO) to give 5-62% electrophilic trapping products, e.g. II (R = Cl, Br, NHAc, Ph, OCFMe₂), 7-42% 2-pyridyl triflate (II, R = O₃SCF₃), and 4-15% 2-fluoropyridine (II, R = F).

Tetrahedron Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C10H11NO4, Name: 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Umemoto, Teruo published the artcilePreparation of 2-fluoropyridines via base-induced decomposition of N-fluoropyridinium salts, Safety of 1-Fluoropyridiniumtriflate, the publication is Journal of Organic Chemistry (1989), 54(7), 1726-31, database is CAplus.

N-Fluoropyridinium salts with either BF₄^–, SbF₆^–, or PF₆^– as the counterion were treated with excess base, such as Et₃N, at room temperature to give 2-fluoropyridines in good yield. This method was successfully applied to the preparation of 2-fluoropyridine derivatives possessing electron-donating or withdrawing substituents from the substituted N-fluoropyridinium tetrafluoroborates. Pyridine-F₂ compounds produced through reactions of pyridines with mol. F (caution, toxic) were also treated with a base to give 2-fluoropyridines but in low yields. These reactions are considered to occur through a carbene mechanism as follows: a novel N-F-containing cyclic carbene generated from the N-fluoropyridinium salts by 2-proton abstraction, reacts with F atoms from the counterions, followed by elimination of F^– from the N-F moiety to yield 2-fluoropyridines. Previously reported findings in reactions of pyridines with mol. F are explained on the basis of this mechanism.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C27H39ClN2, Safety of 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem