785-93-3Relevant academic research and scientific papers
Tandem reductive perfluoroalkylation of esters with perfluoroalkyl titanate-type reagents
Mikami, Koichi,Murase, Tatsushi,Itoh, Yoshimitsu
, p. 11686 - 11687 (2007)
The generation of stable perfluoroalkyl titanate-type reagents and their new type of reaction, tandem reductive perfluoroalkylation of esters, are shown to give perfluoroalkylated sec-alcohols in up to quantitative yield. Copyright
Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands
Brüning, Fabian,Nagae, Haruki,K?ch, Daniel,Mashima, Kazushi,Togni, Antonio
supporting information, p. 10818 - 10822 (2019/07/31)
The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.
Phosphate management with small molecules
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, (2015/12/17)
This invention relates to methods and small molecules having a phosphate group that can be used to inhibit phosphate transport and to treat or prevent diseases that are related to disorders in the maintenance of normal serum phosphate levels.
Method for Producing Fluorine-Containing Substituted Compound and Fluorine-Containing Substituted Compound
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Paragraph 0240-0254, (2014/02/15)
A method for producing a fluorine-containing substituted compound, the method including: introducing an organofluorine compound and an organolithium compound into a microreactor provided with a flow path capable of mixing a plurality of liquids, to thereby obtain a reaction product; and introducing, into the microreactor, the reaction product and an electrophile exhibiting electrophilic effect on the reaction product, to thereby obtain a fluorine-containing substituted compound.
Perfluoroalkylation in flow microreactors: Generation of perfluoroalkyllithiums in the presence and absence of electrophiles
Nagaki, Aiichiro,Tokuoka, Shinya,Yamada, Shigeyuki,Tomida, Yutaka,Oshiro, Kojun,Amii, Hideki,Yoshida, Jun-Ichi
supporting information; experimental part, p. 7559 - 7563 (2011/12/03)
Perfluoroalkyllithiums were effectively generated from perfluoroalkyl halides in the presence and absence of electrophiles using flow microreactor systems. The in situ trapping with electrophile is conducted at much higher temperatures than those required for batch macro reactors. The subsequent trapping method is quite effective for highly reactive electrophiles that are not compatible with the lithiation process.
Novel reduction of perfluoroalkyl ketones with lithium alkoxides
Sokeirik, Yasser S.,Sato, Kazuyuki,Omote, Masaaki,Ando, Akira,Kumadaki, Itsumaro
, p. 150 - 152 (2008/09/17)
The reaction of tert-butyl N-(2-bromophenyl)carbamate (1) with ethyl perfluorooctanoate in the presence of tert-butyllithium did not give the desired N-(2-perfluorooctanoylphenyl)carbamate (3) but gave 1-hydroxy-1H-perfluorooctyl compound (4), which was supposed to be formed by the reduction of 3. A similar reaction of 2,2,2-trifluoroacetophenone with tert-butyllithium did not gave any reduction product. Detailed investigation showed that lithium ethoxide worked as the reducing agent of this abnormal reduction. By the reaction of lithium isopropoxide, an aldol product from 2,2,2-trifluoroacetophenone with acetone was isolated, while perfluoroheptyl or perfluoropropyl phenyl ketones were reduced by this alkoxide in a high yield without formation of the aldol adduct.
Process for preparing polyfluoroalkylithium compounds
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Page/Page column 5-6, (2010/02/11)
The invention relates to a process for preparing polyfluoroalkyl-lithium compounds by deprotonation of polyfluoroalkyl compounds by means of lithium bases.
An efficient dehyrohalogenation method for the synthesis of α,β,β-trifluorostyrenes, α-chloro-β,β- difluorostyrenes and E-1-arylperfluoroalkenes
Anilkumar,Burton, Donald J.
, p. 1174 - 1184 (2007/10/03)
Dehydrofluorination of 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF 3) and 1-aryl-1-chloro-2,2,2-trifluoroethane (ArCHClCF3) using lithiumhexamethyldisilazide (LHMDS) in tetrahydrofuran (THF) at room temperature produced 1,2,2-trifluorostyrene and 1-chloro-2,2-difluorostyrene, respectively, in very good isolated yields. Dehydrofluorination of 1,2,2,3,3,3-hexafluoro-1-phenyl-propane (PhCHFCF2CF3) and 1,2,2,3,3,4,4,4-octafluoro-1-phenyl-butane (PhCHFCF2CF 2CF3) using LHMDS produced the corresponding substituted olefins (1-phenyl-1,2,3,3,3-pentafluoroprop-1-ene and 1-phenyl-1,2,3,3,4,4,4- pentafluorobut-1-ene) in good yield and high E-selectivity. Dehydrofluorination of 1-chloro-1-phenyl-2,2,3,3,3-pentafluoropropane (PhCHClCF2CF 3) and 1-chloro-1-phenyl-2,2,3,3,4,4,4-heptafluorobutane (PhCHClCF2CF2CF3) produced a mixture of the corresponding E and Z olefins (PhCClCFCF3 and PhCClCFCF 2CF3) in good yield.
A simple procedure for nucleophilic perfluoroalkylation of organic and inorganic substrates
Petrov, Viacheslav A.
, p. 3267 - 3269 (2007/10/03)
The mixture RfI and tetrakis(dimethylamino)ethylene is used for the nucleophilic perfluoroalkylation. The reaction of chlorotrimethylsilane and RfI/tetrakis(dimethylamino)ethylene in diglyme results in the formation of RfSi(CH3)3 isolated in 55-81% yield. The interaction of this system with organic electrophiles such as benzoyl and benzensulphonyl chlorides, aliphatic and aromatic aldehydes and activated ketones leads to the formation of the corresponding condensation products in 24-62% yield.
