39077-43-5Relevant academic research and scientific papers
Nucleophilic reactivity. Kinetics of reactions between diarylamines N-anions and hexafluorobenzene or pentafluoropyridine in dimethyl sulfoxide
Os'kina,Vlasov
, p. 260 - 269 (2001)
Rate constants of reactions between sodium salts of diarylamines N-anions and hexafluorobenzene and pentafluoropyridine in DMSO at 25°C were determined. The Bronsted factors for substrates under consideration are 0.14 and 0.34 respectively. These data evi
Fluorinated Aminopyridines: Synthesis, Structure, and Rare Liquid-Liquid Cocrystal Formation Driven by Unusually Short N-H···F-C Hydrogen Bonding
Iacono, Scott T.,Jennings, Abby R.,Kure, Daniel A.,McMillen, Colin D.,Peloquin, Andrew J.,Pennington, William T.
, p. 5484 - 5492 (2020)
The role of hydrogen bonding in the crystal packing of a series of 4-aminoperfluoropyridines was studied using single-crystal X-ray crystallography. The aminoperfluoropyridines were synthesized using only excess amine to serve as both nucleophile and base. Instead of addition to the perfluoropyridine ring, a strong N-H···F-C hydrogen bond led to cocrystal formation of perfluoropyridine with sterically hindered amines dicyclohexylamine as well as 2-methylpiperdine. This formation is, to our knowledge, the first report of two nonreacting liquids, consisting of only discrete small molecules, combining to form a cocrystalline solid stable under ambient conditions. Perfluoropyridine is stabilized in the crystal lattice approximately 100 °C above its normal boiling point.
Continuous flow glassware reactors for the laboratory. Synthesis of 2-alkoxy-4-aminotrifluoropyridine derivatives from pentafluoropyridine
Chambers, Richard D.,Sandford, Graham,Trmcic, Jelena
, p. 1439 - 1443 (2007)
Simple, general use continuous flow glassware reactors that are constructed by standard glass blowing techniques have been designed and used for various nucleophilic aromatic substitution reactions. The glassware flow reactors, consisting of a reaction channel that is 0.5 mm in diameter and may possess a range of inlet and outlet ports, provide the opportunity for research scientists to use inexpensive, conveniently operated continuous flow methodology in the laboratory environment. A short series of 2-alkoxy-4-aminotrifluoropyridine derivatives was prepared from pentafluoropyridine in a single continuous flow process by sequential nucleophilic aromatic substitution.
Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
Brittain, William D. G.,Cobb, Steven L.
supporting information, p. 5793 - 5798 (2021/08/01)
This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
Fluorene compound and organic electroluminescent device thereof
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Paragraph 0134-0137; 0151-0153, (2021/11/03)
The invention provides a fluorene compound and an organic electroluminescent device thereof. Belong to organic electroluminescence technical field. When the fluorene compound is used as a cover layer material, light can be effectively inhibited from being scattered from the cathode composite layer to a far distance from the cathode composite layer, light can be scattered from different directions of the cathode of the organic electroluminescent device, light transmittance of the device can be effectively weakened. Fluorene compound and organic electroluminescent device thereof The utility model has good application effect and industrialization prospect.
Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control
Khaled, Mohammad B.,El Mokadem, Roukaya K.,Weaver, Jimmie D.
supporting information, p. 13092 - 13101 (2017/09/26)
The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H's. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.
Synthesis of substituted imidazopyridines from perfluorinated pyridine derivatives
Poorfreidoni, Alireza,Ranjbar-Karimi, Reza
, p. 5781 - 5783 (2016/12/06)
4-Phenylsulfonyl tetrafluoropyridine was reacted with various N-aryl amidines to give the corresponding imidazopyridine systems via an intramolecular nucleophilic aromatic substitution process whilst pentafluoropyridine gave N′-(perfluoropyridin-4-yl)-N-p
Mechanisms of reactions of halogenated compounds. Part 7. Effects of fluorine and other groups as substituents on nucleophilic aromatic substitution
Chambers, Richard D.,Martin, Peter A.,Sandford, Graham,Williams, D. Lyn H.
experimental part, p. 998 - 1002 (2009/04/04)
The effect of fluorine as a substituent group on nucleophilic aromatic substitution is discussed, where a fluorine atom located ortho to the point of substitution may be of variable activating influence, whereas fluorine located para is slightly deactivat
