Category: 107263-95-6

Ball, Nicholas D. published the artcileMechanistic and Computational Studies of Oxidatively-Induced Aryl-CF₃ Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation, Related Products of pyridine-derivatives, the publication is Journal of the American Chemical Society (2011), 133(19), 7577-7584, database is CAplus and MEDLINE.

This article describes the rational design of first generation systems for oxidatively induced Aryl-CF₃ bond-forming reductive elimination from Pd^II. Treatment of (dtbpy)Pd^II(Aryl)(CF₃) (dtbpy = di-tert-butylbipyridine) with NFTPT (N-fluoro-1,3,5-trimethylpyridinium triflate) afforded the isolable Pd^IV intermediate (dtbpy)Pd^IV(Aryl)(CF₃)(F)(OTf). Thermolysis of this complex at 80° resulted in Aryl-CF₃ bond-formation. Detailed exptl. and computational mechanistic studies have been conducted to gain insights into the key reductive elimination step. Reductive elimination from this Pd^IV species proceeds via pre-equilibrium dissociation of TfO^– followed by Aryl-CF₃ coupling. DFT calculations reveal that the transition state for Aryl-CF₃ bond formation involves the CF₃ acting as an electrophile with the Aryl ligand serving as a nucleophilic coupling partner. These mechanistic considerations along with DFT calculations have facilitated the design of a second generation system utilizing the tmeda (N,N,N’,N’-tetramethylethylenediamine) ligand in place of dtbpy. The tmeda complexes undergo oxidative trifluoromethylation at room temperature

Journal of the American Chemical Society 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, Related Products of pyridine-derivatives.

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

Suzuki, Shoko published the artcileAsymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates, COA of Formula: C6H5F4NO3S, the publication is Tetrahedron: Asymmetry (2006), 17(4), 504-507, database is CAplus.

Novel chiral rare earth metal complexes bearing perfluorinated binaphthyl phosphate ligand RE[(R)-F₈BNP]₃ (RE = rare earth; F₈BNP = 5,5′,6,6′,7,7′,8,8′-octafluoro-1,1′-binaphthyl-2,2′-diyl phosphate) have been synthesized and used as a catalyst for the asym. electrophilic fluorination reaction of β-keto esters. The target catalysts are tris[(11bR)-8,9,10,11,12,13,14,15-octafluoro-4-(hydroxy-κO)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin 4-(oxide-κO)]scandium, lanthanum, gadolinium, ytterbium, indium complexes. The use of Sc[(R)-F₈BNP]₃ catalyst in combination with 1-fluoropyridinium triflate (NFPY-OTf) as a fluorinating agent was found to give the desired α-fluoro-β-keto esters in high chem. yields and enantiomeric excesses (up to 88% ee) under mild conditions.

Tetrahedron: Asymmetry 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 C5H6BNO2, COA of Formula: C6H5F4NO3S.

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

Suzuki, Katsutoshi published the artcileElectrolytic Partial Fluorination of Organic Compounds.71.Highly Diastereoselective Anodic Fluorination of Sulfides Having Oxygen-Containing Heterocyclic Groups, SDS of cas: 107263-95-6, the publication is Journal of Organic Chemistry (2004), 69(4), 1276-1282, database is CAplus and MEDLINE.

Racemic and nonracemic α-fluoro-β-alkoxysulfides and (arylsulfanylfluoromethyl)dioxolanes such as I are prepared stereoselectively by electrochem. fluorination of β-alkoxysulfides and (arylsulfanylmethyl)dioxolanes such as II with Et₃N•3HF in acetonitrile. The 2-spirocyclohexyl-1,3-dioxolanemethyl sulfide II gives the desired α-fluorosulfide in 54% yield and with 80% de.; other sulfides give the desired product in in 10-77% yields and with 13-70% de. The diastereoselectivity of the electrochem. fluorination increases with decreasing Gutmann donor number of the solvent. Et₃N•3HF is the most effective fluorination electrolyte used; other amine hydrofluorides give fluorinated product in 0-8% yields and with reduced stereoselectivity. Chem. fluorination of II using Selectfluor also gives I, but in only 5% yield and in 32% de.; chem. fluorination using N-fluoropyridinium salts gives no fluorination products. Decomposition occurs upon acidic hydrolysis of I; oxidation of I to the Ph sulfone followed by acidic hydrolysis yields the nonracemic fluoroinated dihydroxysulfone III. The structure and stereochem. of dioxolanone IV is determined by X-ray crystallog.

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 C9H9ClN2, SDS of cas: 107263-95-6.

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

Umemoto, Teruo published the artcilePower- and structure-variable fluorinating agents. The N-fluoropyridinium salt system, Computed Properties of 107263-95-6, the publication is Journal of the American Chemical Society (1990), 112(23), 8563-75, database is CAplus.

The usefulness of the N-fluoropyridinium salt system as a source of fluorinating agents was examined by using substituted or unsubstituted N-fluoropyridinium triflates, N-fluoropyridinium salts possessing other counteranions, and two N-fluoropyridinium-2-sulfonates (I). Electrophilic fluorinating power varied remarkably according to the electronic nature of the ring substituents. This power increased as the electron d. of pos. N sites decreased, and this was correlated to the pK_a values of the corresponding pyridines. By virtue of this variation, it was possible to fluorinate a wide range of nucleophile substrates differing in reactivity, e.g., aromatics, carbanions, active methylene compounds, enol alkyl or silyl ethers, vinyl acetates, ketene silyl acetals, and olefins. All the reactions could be explained on the basis of a one-electron-transfer mechanism. N-Fluoropyridinium salts showed high chemoselectivity in fluorination, the extent depending on the reactive moiety. Selective 9α-fluorination of steroids was carried out with the tris(trimethylsilyl ether) of a triketo steroid. Regio- or stereoselectivity in fluorination was determined by N-fluoropyridinium salt structure. Steric bulkiness of the N-F surroundings hindered the orthofluorination of phenols and aniline derivatives, while the capacity for H bonding on the part of the counteranions prompted this process, and I underwent this fluorination exclusively or almost so. Two bulky N-fluoropyridinium triflates preferentially attacked the 6-position of the conjugated vinyl ester of a steroid from the unhindered β-direction to give a thermally unstable 6β-fluoro isomer. N-Fluoropyridinium salt systems can serve as a source of the most ideal fluorinating agents for conducting desired selective fluorination through fluorinating capacity or structural alteration.

Journal of the American Chemical Society 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 C18H35NO, Computed Properties of 107263-95-6.

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

Bew, Sean P. published the artcileOrganocatalytic Aziridine Synthesis Using F⁺ Salts, Product Details of C6H5F4NO3S, the publication is Organic Letters (2009), 11(20), 4552-4555, database is CAplus and MEDLINE.

This paper describes a unique application of the fluoronium cation (F⁺) as an organocatalyst for mediating the reaction between N-substituted imines and Et diazoacetate affording excellent yields of N-substituted aziridines. E.g., N-fluoropyridinium triflate catalyzed the reaction of (E)-N-arylimine I with Et diazoacetate to give 83% cis-aziridine II.

Organic 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, Product Details of C6H5F4NO3S.

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

Chung, Yongseog published the artcileStructural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts, Computed Properties of 107263-95-6, the publication is Journal of Organic Chemistry (1989), 54(5), 1018-32, database is CAplus.

A fairly broad study of how the structure of an anthracene cycloadduct affects the rate of its cycloreversion reaction was undertaken. Conclusions were drawn based on the rate constants for retro-Diels-Alder (rDA) reactions of a variety of anthracene-type adducts conducted in di-Ph ether. The rDA reaction of anthracene cycloadducts is influenced by diene substituents in the following ways: (1) electron-donating groups increase the reaction rate, and the accelerating effect is subject to geometric modulation for a conjugating substituent like dimethylamino; (2) electron-withdrawing groups may decrease or increase the reaction rate, although the effect is rarely large; and (3) steric acceleration is relatively small and demonstrates an unprecedented bell-shaped structure-reactivity profile. Peripheral substitution of the adduct with siloxy groups results in a significant acceleration, even though the groups are three bonds removed from the reaction site. The same reaction is influenced by dienophile substituents in the following ways: (1) electron-withdrawing groups increase the rate of the reaction; (2) strongly conjugating substituents make the reaction much faster than predicted by classical electron-withdrawing or -donating ability due to a change to polar mechanism; and (3) there is no observable steric effect.

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, Computed Properties of 107263-95-6.

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

Pang, Yuan-Ping published the artcileSmall molecules showing significant protection of mice against botulinum neurotoxin serotype A, COA of Formula: C6H5F4NO3S, the publication is PLoS One (2010), 5(4), No pp. given, database is CAplus and MEDLINE.

Botulinum neurotoxin serotype A (BoNTA) causes a life-threatening neuroparalytic disease known as botulism that could afflict large, unprotected populations if the toxin were employed in an act of bioterrorism. Current post-exposure therapy is limited to symptomatic treatment or passive immunization that is effective for treating infant botulism at a cost of US $45,300 per treatment regimen. Antibodies can neutralize the extracellular but not the intracellular BoNTA. Moreover, antibody production, storage, and administration in a mass casualty scenario pose logistical challenges. Alternatively, small-mol. inhibitors of BoNTA endopeptidase (BoNTAe) are sought to antagonize the extracellular or intracellular toxin. While several such mols. reportedly demonstrated efficacy in protecting cells against BoNTA, there is scant information to show that small mols. can significantly protect mammals against BoNTA. Herein the authors report the development of effective small-mols. BoNTAe inhibitors with promising in vivo pharmacokinetics. One such mol. has an in vivo half-life of 6.5 h and is devoid of obvious sign of toxicity. Pre-treatment with this mol. at 2 mg/kg protected 100% and 70% of treated mice against BoNTA at 5 times of its median-LD during the periods of 2 and 4 half-lives of the inhibitor, resp. In contrast, 40% and 0% of untreated mice survived during the resp. periods. Similar levels of protection were also observed with two other small mols. These results demonstrate that small mols. can significantly protect mice against BoNTA and support the pursuit of small-mol. antagonists as a cost-effective alternative or as an adjunct to passive immunity for treating botulism.

PLoS One 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, COA of Formula: C6H5F4NO3S.

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

Vincent, Stephane P. published the artcileElectrophilic Fluorination-Nucleophilic Addition Reaction Mediated by Selectfluor: Mechanistic Studies and New Applications, Application of 1-Fluoropyridiniumtriflate, the publication is Journal of Organic Chemistry (1999), 64(14), 5264-5279, database is CAplus and MEDLINE.

The electrophilic fluorination-nucleophilic addition reaction with Selectfluor-type reagents upon glycals has been studied and optimized. This reaction leads to selective fluorination at the 2-position with concomitant nucleophilic addition to the anomeric center. To understand the stereochem. outcome of this process, a mechanistic study has led to the discovery that, in the fucose series, Selectfluor adds specifically in a syn manner, yielding a 1-[TEDA-CH₂Cl]-2-fluoro saccharide that anomerizes slowly to a more stable intermediate. The anomeric α/β distribution was studied as a function of reactants and conditions, and it was found that a judicious choice of protective group strategy can improve the stereoselectivity of both fluorination and nucleophilic addition Furthermore, a hypersensitive radical probe was used to probe the reaction, and no product characteristic of a radical process was isolated, suggesting that no single electron transfer occurs during the attack of the glycal on Selectfluor. The importance of solvent effect, Selectfluor counterion, and stepwise procedure has also been discussed. This study has brought an important improvement of yields and a broader range of allowed nucleophiles such as secondary alcs. of carbohydrates, amino acids, phosphates, or phosphonates. This optimized process was further applied to the modification of important bioactive mols., including the synthesis of fluorinated daunomycin and oleandrin analogs and the oxidation of thio glycosides to the corresponding sulfoxides.

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 C11H11BFNO4, Application of 1-Fluoropyridiniumtriflate.

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

Banks, R. Eric published the artcileN-Fluoropyridinium trifluoromethanesulfonate and 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate: the first experimental determination of the F-N⁺ bond length involving sp² nitrogen, Safety of 1-Fluoropyridiniumtriflate, the publication is Acta Crystallographica, Section C: Crystal Structure Communications (2003), C59(4), m141-m143, database is CAplus and MEDLINE.

The crystal structures of N-fluoropyridinium trifluoromethanesulfonate (I) and 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate (II) were determined I is monoclinic, space group P2₁/c, with a 6.027(2), b 12.901(4), c 12.490(3) Å, β 103.96(3)°; Z = 4, d_c = 1.742; R = 0.045, R_w(F²) = 0.149 for 1658 reflections. II is monoclinic, space group P2₁/n, with a 7.616(2), b 11.843(3), c 14.924(3) Å, β 97.43(2)°; Z = 4, d_c = 2.119; R = 0.034, R_w(F²) = 0.071 for 2335 reflections. The N-F bond lengths in I, a known electrophilic fluorinating agent, and its novel analog II are 1.357(4) and 1.354(4) Å, resp.

Acta Crystallographica, Section C: Crystal Structure Communications 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, Safety of 1-Fluoropyridiniumtriflate.

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

Rozatian, Neshat published the artcileEnolization rates control mono- versus di-fluorination of 1,3-dicarbonyl derivatives, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Chemical Science (2019), 10(44), 10318-10330, database is CAplus and MEDLINE.

Fluorine-containing 1,3-dicarbonyl derivatives are essential building blocks for drug discovery and manufacture To understand the factors that determine selectivity between mono- and di-fluorination of 1,3-dicarbonyl systems, we have performed kinetic studies of keto-enol tautomerism and fluorination processes. Photoketonization of 1,3-diaryl-1,3-dicarbonyl derivatives and their 2-fluoro analogs is coupled with relaxation kinetics to determine enolization rates. Reaction additives such as water accelerate enolization processes, especially of 2-fluoro-1,3-dicarbonyl systems. Kinetic studies of enol fluorination with Selectfluor and NFSI reveal the quant. effects of 2-fluorination upon enol nucleophilicity towards reagents of markedly different electrophilicity. Our findings have important implications for the synthesis of α,α-difluoroketonic compounds, providing valuable quant. information to aid in the design of fluorination and difluorination reactions.

Chemical Science 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