85465-50-5Relevant academic research and scientific papers
Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride
Hammond, Gerald B.,Li, Wangbing,Lu, Zhichao,Xu, Bo
supporting information, p. 9640 - 9644 (2021/12/14)
An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26–SO42–), which could be reused after filtration. Moreover, A26–SO42– can be used in continuous flow conditions. In our conditions, water is well-tolerated.
Catalytic Promiscuity of Transaminases: Preparation of Enantioenriched β-Fluoroamines by Formal Tandem Hydrodefluorination/Deamination
Cuetos, Aníbal,García-Ramos, Marina,Fischereder, Eva-Maria,Díaz-Rodríguez, Alba,Grogan, Gideon,Gotor, Vicente,Kroutil, Wolfgang,Lavandera, Iván
supporting information, p. 3144 - 3147 (2016/03/12)
Transaminases are valuable enzymes for industrial biocatalysis and enable the preparation of optically pure amines. For these transformations they require either an amine donor (amination of ketones) or an amine acceptor (deamination of racemic amines). Herein transaminases are shown to react with aromatic β-fluoroamines, thus leading to simultaneous enantioselective dehalogenation and deamination to form the corresponding acetophenone derivatives in the absence of an amine acceptor. A series of racemic β-fluoroamines was resolved in a kinetic resolution by tandem hydrodefluorination/deamination, thus giving the corresponding amines with up to greater than 99 % ee. This protocol is the first example of exploiting the catalytic promiscuity of transaminases as a tool for novel transformations.
Synthesis of α-Fluoroketones by Insertion of HF into a Gold Carbene
Zeng, Xiaojun,Liu, Shiwen,Shi, Zhenyu,Liu, Guangchang,Xu, Bo
supporting information, p. 10032 - 10036 (2016/08/16)
Reported is an efficient synthesis of α-fluoroketones by insertion of hydrogen fluoride (HF) into the gold carbene intermediate, generated from a cationic gold catalyzed addition of N-oxides to alkynes. This method results in excellent chemical yields for a wide range of alkyne substrates and demonstrates good functional-group tolerance.
A Practical Synthesis of α-Fluoroketones in Aqueous Media by Decarboxylative Fluorination of β-Ketoacids
Li, Jian,Li, Yin-Long,Jin, Nan,Ma, Ai-Lun,Huang, Ya-Nan,Deng, Jun
supporting information, p. 2474 - 2478 (2015/08/18)
A practical and novel process for the decarboxylative fluorination of β-ketoacids in water in the presence of phase transfer catalyst has been developed, affording a series of α-fluoroketones in good to excellent yields. Furthermore, a preliminary investigation for the catalytic asymmetric transformation was performed and a proposed mechanistic pathway for this catalytic process was proposed.
Synthesis of enantiopure fluorohydrins using alcohol dehydrogenases at high substrate concentrations
Borzeicka, Wioleta,Lavandera, Ivan,Gotor, Vicente
, p. 7312 - 7317 (2013/08/23)
The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.
Novel entry to aryl α-fluoromethyl ketones via sodium hydroxide-induced hydrolysis of fluorinated enol tosylates
Funabiki,Fukushima,Sugiyama,Shibata,Matsui
, p. 1308 - 1310 (2007/10/03)
Abstract: 1-Aryl-substituted 2,3,3-trifluoro-1-propenyl p-toluene-sulfonate 1 was smoothly hydrolyzed in a mixed solvent of dimethyl sulfoxide-water (1:1) in the presence of sodium hydroxide at 80 °C to afford the corresponding aryl α-monofluoromethyl ketones 2 in fair to good yields.
Compounds and methods for treating depression
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, (2008/06/13)
Compounds of the formula: STR1 wherein: X is fluorine, chlorine, or bromine; R is the group R2 as defined below; R1 is a group of the formula: STR2 or the group R2 as defined below; wherein R2 is: STR3 wherein R
