350-50-5Relevant articles and documents
C?F Bond Activation by Silylium Cation/Phosphine Frustrated Lewis Pairs: Mono-Hydrodefluorination of PhCF3, PhCF2H and Ph2CF2
Mallov, Ian,Ruddy, Adam J.,Zhu, Hui,Grimme, Stefan,Stephan, Douglas W.
, p. 17692 - 17696 (2017)
Single defluorination of aryl polyfluoromethyl functionalities is achieved by both intra- and intermolecular silylium cation/phosphine Lewis pairs. Phosphine-captured aryl fluoromethyl cations are then treated with Br?nsted base to complete the first mono
Catalytic Formation of C(sp3)-F Bonds via Heterogeneous Photocatalysis
Tarantino, Giulia,Hammond, Ceri
, p. 10321 - 10330 (2018)
Due to their chemical, physical, and biological properties, fluorinated compounds are widely employed throughout society. Yet, despite their critical importance, current methods of introducing fluorine into compounds suffer from severe drawbacks. For example, several methods are noncatalytic and employ stoichiometric equivalents of heavy metals. Existing catalytic methods, on the other hand, exhibit poor activity, generality, selectivity and/or have not been achieved by heterogeneous catalysis, despite the many advantages such an approach would provide. Here, we demonstrate how selective C(sp3)-F bond synthesis can be achieved via heterogeneous photocatalysis. Employing TiO2 as photocatalyst and Selectfluor as mild fluorine donor, effective decarboxylative fluorination of a variety of carboxylic acids can be achieved in very short reaction times. In addition to displaying the highest turnover frequencies of any reported fluorination catalyst to date (up to 1050 h-1), TiO2 also demonstrates excellent levels of durability, and the system is catalytic in the number of photons required; i.e., a photon efficiency greater than 1 is observed. These factors, coupled with the generality and mild nature of the reaction system, represent a breakthrough toward the sustainable synthesis of fluorinated compounds.
New fluoride ion reagent from pentafluoropyridine
Murray, Christopher B.,Sandford, Graham,Korn, Stewart R.,Yufit, Dmitrii S.,Howard, Judith A.K.
, p. 571 - 576 (2005)
A new nucleophilic fluorinating agent, derived from reaction of dimethylaminopyridine (DMAP) with pentafluoropyridine, has been synthesised and assessed in various carbon-fluorine bond forming processes.
Acceleration of the Fluorination of Benzyl Halide by the Combination of Lead Fluoride and Sodium Salt
Ichihara, Junko,Hanafusa, Terukiyo,Takai, Yoshio,Ito, Yoshiaki
, p. 1161 - 1164 (1992)
A new composite reagent, a combination of lead fluoride (PbF2) and a small amount of sodium salt (NaX, X=F, Br etc.) was found to be useful for facilitating heterogeneous fluorination of substituted benzyl halides in acetonitrile.
Tetraphenylphosphonium Hydrogendifluoride: a New Source of Fluoride Ion
Brown, Stephen J.,Clark, James H.
, p. 672 - 673 (1985)
Tetraphenylphosphonium hydrogendifluoride, a soluble and thermally stable reagent, acts as a source of fluoride ion in a variety of organic reactions.
Swain,Spalding
, p. 6104 (1960)
SUBSTRATE DEPENDENT SOLVENT EFFECTS IN NUCLEOPHILIC FLUORINE TRANSFER REACTIONS
Clark, J. H.,MacQuarrie, D.
, p. 591 - 596 (1987)
The rate of fluorination of organic substrates by potassium fluoride in aprotic solvents is subject to substrate dependent solvent effects.
Bethell et al.
, p. 1447 (1977)
Reaction evolution of a solvate fluoride ionic liquid induced fluorination process probed by Raman spectroscopy
Chen, Zhengfei,Deng, Meng,Gao, Zhanghua,Jiang, Zhijiang,Li, Lichun,Tang, Haodong
, (2020)
Currently, about 30% of new approved drugs contained fluorine atoms and most of them are made through fluorination reactions using various kinds of fluorinating reagents. In the current work, we report a facile and more accessible way to probe the fluorination evolution at different stages using a newly developed fluorinating reagent (1-ethyl-3-methylimmidazolium fluoride-ethylene glycol, [C2C1im]F-EG). Benzyl bromide was converted to benzyl fluoride using this fluorinating reagent under mild conditions. A more accessible Raman method, compared to NMR, was used to probe the reaction process due to the products having their own characteristic Raman vibrational frequencies because of the formation of different C-X bonds. Thus the yield of the product at different time scales could be then quantified based on their relative intensities, providing a fresh insight into the fluorination process. This method could be applied in other reactions to reflect the important fluorination process, which methodologically reports a facile way to probe reaction processes.
METHOD AND REAGENT FOR DEOXYFLUORINATION
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Paragraph 0148-0150; 0152; 0160, (2021/05/29)
A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.
PROCESSES FOR FLUORINATION
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Paragraph 0188, (2020/03/05)
The present technology relates to fluorination reactions. Specifically, processes useful for making the fungicide compound, DFT are disclosed. More broadly, also disclosed herein are processes useful for deoxyfluorination at the α-aromatic position of a given compound.