113281-23-5Relevant articles and documents
Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones
Xie, Lihua,Dong, Shunxi,Zhang, Qian,Feng, Xiaoming,Liu, Xiaohua
supporting information, p. 87 - 90 (2019/01/03)
The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.
Nucleophilic trifluoromethylation of carbonyl compounds and disulfides with trifluoromethane and silicon-containing bases
Large,Roques,Langlois
, p. 8848 - 8856 (2007/10/03)
Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)2N- M+, generated in situ from N(TMS)3 and M+ F- or RO- Na+. When F- is used in a catalytic amount, silylated α-(trifluoromethyl)carbinols are obtained: In this case, the four-component system HCF3/N(TMS)3/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)3/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of awl disulfides whereas N(SiMe3)3/F- is Well suited to that of aliphatic disulfides.
A New Method for Synthesis of Trifluoromethyl-Substituted Phenols and Anilines
Stahly, G. Patrick,Bell, Donald R.
, p. 2873 - 2877 (2007/10/02)
Triethyl(trifluoromethyl)silane and tri-n-butyl(trifluoromethyl)silane were found to react with quinones by addition to one of the carbonyl carbon atoms, giving dienones containing geminal trifluoromethyl and trialkylsiloxy substituents.These reactions were catalyzed by a variety of basic compounds.Quinones found to undergo this process include 1,2- and 1,4-benzoquinones (some bearing alkyl substituents), naphthoquinone, anthraquinone, and phenanthrenequinone.Most of the resulting dienones gave (trifluoromethyl)phenols on dissolving matal reduction, and one was subjected to reductive amination to give (trifluoromethyl)aniline.