107018-38-2Relevant academic research and scientific papers
A simple procedure for nucleophilic perfluoroalkylation of organic and inorganic substrates
Petrov, Viacheslav A.
, p. 3267 - 3269 (2001)
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.
Sodium trifluoroacetate: An efficient precursor for the trifluoromethylation of aldehydes
Chang, Ying,Cai, Chun
, p. 3161 - 3164 (2005)
In a convenient and efficient procedure, the nucleophilic trifluoromethylation of aldehydes with sodium trifluoroacetate was achieved, using copper(I) halides as the catalyst.
A chiral triaminosulfonium salt: Design and application to catalytic asymmetric synthesis
Kuroki, Yoshichika,Iseki, Katsuhiko
, p. 8231 - 8234 (1999)
The first chiral triaminosulfonium salt, tris((S,S)-3,4-diphenylpyrrolidino)sulfonium difluorotriphenylstannate, catalyzes trifluoromethylation of benzaldehyde with (trifluoromethyl)trimethylsilane to give the corresponding optically active alcohol with 52% ee.
Fluoroform: An efficient precursor for the trifluoromethylation of aldehydes
Folleas, Benoit,Marek, Ilan,Normant, Jean-F,Jalmes, Laurent Saint
, p. 2973 - 2976 (1998)
Fluoroform is shown to be an efficient trifluoromethylating agent when deprotonated using standard reagents in DMF. The important role of DMF in that reaction was demonstrated.
Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and imines with (perfluoroalkyl)trimethylsilane
Kawano, Yoshikazu,Kaneko, Nobuya,Mukaiyama, Teruaki
, p. 1133 - 1145 (2006)
Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and aldimines with (perfluoroalkyl)trimethylsilanes (TMSCF3, TMSC 2F5, and TMSC3F7) is described. The nitrogen- or oxygen-containing anions generated from amides, imides, and carboxylic acids have been found to work as effective Lewis-base catalysts in perfluoroalkylation that proceeds via activation of the carbon-silicon bonds of (perfluoroalkyl)trimethylsilanes. Reactions of carbonyl compounds such as aldehydes, ketones, and esters with TMSCF3 in the presence of a catalytic amount of Lewis bases proceeded smoothly to afford the corresponding adducts in good-to-high yields under mild conditions. Although it was considered difficult, this catalytic perfluoroalkylation of various aldimines with (perfluoroalkyl)trimethylsilane in the presence of Lewis bases such as lithium acetate or benzoate proceeded efficiently to give the corresponding perfluoroalkylated adducts, because the aldimines here were weak electrophiles toward (perfluoroalkyl)trimethylsilanes. The present reaction is, therefore, the first example of a catalytic perfluoroalkylation of aldimines.
Organocatalysis approach to trifluoromethylation with fluoroform
Zhang, Yuan,Fujiu, Motohiro,Serizawa, Hiroki,Mikami, Koichi
, p. 367 - 371 (2013)
The organic base methodology exploits an access to generate the "trifluoromethyl anion" for carbonyl, ester, acid halide, epoxide, deuterium donor, and carbon dioxide substrates to afford the trifluoromethylation products with good overall efficiency even in organocatalysis conditions. The NMR analysis of the mixture of fluoroform and P4-base shows no change thereof. However, on addition of electrophiles, the trifluoromethylation products were obtained efficiently.
Fluoroform: An efficient precursor for the trifluoromethylation of aldehydes
Folléas, Beno?t,Marek, Ilan,Normant, Jean-F.,Saint-Jalmes, Laurent
, p. 275 - 283 (2000)
Fluoroform is shown to be an efficient trifluoromethylating agent when deprotonated using standard reagents in DMF. The important role of DMF as a solvent but also as a reactant was demonstrated.
BIARYL PYRAZOLES AS NRF2 REGULATORS
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Page/Page column 425; 426, (2017/08/01)
The present invention relates to biaryl pyrazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 regulators.
Chemo- and Enantioselective Addition and β-Hydrogen Transfer Reduction of Carbonyl Compounds with Diethylzinc Reagent in One Pot Catalyzed by a Single Chiral Organometallic Catalyst
Huang, Huayin,Zong, Hua,Bian, Guangling,Song, Ling
, p. 12614 - 12619 (2016/01/09)
Using a single chiral phosphoramide-Zn(II) complex as the catalyst, the asymmetric β-H transfer reduction of aromatic α-trifluoromethyl ketones and enantioselective addition of aromatic aldehydes with Et2Zn in one pot were successfully realized, affording the corresponding additive products of secondary alcohols in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee) and the reduction products of α-trifluoromethyl alcohols in good to excellent yields with up to 77% ee.
Polyfluoroalkylation of carbonyl compounds by polyfluoroalkyl anions generated from polyfluorocarboxamides
Wakita, Natshumi,Hara, Shoji
, p. 1201 - 1212 (2016/11/07)
Polyfluoroalkyl anions, generated by reduction of (polyfluoroalkanoyl)piperidines with Et3BHK, were used for the polyfluoroalkylation of carbonyl compounds. Trifluoromethylation of aromatic aldehydes proceeded in good yields, and that of aliphatic aldehydes afforded a moderate yield. In contrast, the yield was low when the reaction involved benzophenone. Pentafluoroethylation and octafluorobutylation of aldehydes were also carried out by using the corresponding (polyfluoroalkanoyl)piperidines, which were prepared from commercially available polyfluorocompounds. The (polyfluoroalkanoyl)piperidines were also prepared through polyfluorination, and were used in the polyfluoroalkylation of aldehydes.
