1536-02-3Relevant academic research and scientific papers
Efficient synthesis of trifluoromethylated cyclopentadienes/fulvenes/ norbornenes from divinyl ketones
Liu, Xiao,Xu, Xianxiu,Pan, Ling,Zhang, Qian,Liu, Qun
, p. 6703 - 6706 (2013/10/01)
The synthetic methods of trifluoromethylated cyclopentadienes/fulvenes/ norbornenes have been developed using 3-CF3-1,4-dien-3-ols as the synthons, which can be easily prepared by the regiospecific 1,2-addition of the Ruppert-Prakash reagent (TMSCF3) to divinyl ketones. All the reactions are carried out under mild, metal-free conditions to afford the corresponding products in high to excellent yields.
Trifluoromethanesulfinamide from ephedrine: A more efficient trifluoromethylating reagent
Roussel, Solveig,Billard, Thierry,Langlois, Bernard R.,Saint-Jalmes, Laurent
, p. 2119 - 2122 (2007/10/03)
Nucleophilic trifluoromethylation of non-enolizable and enolizable carbonyl compounds was achieved with the trifluoromethanesulfinamide derived from O-silylated ephedrine. In contrast to the trifluoroacetamide analog, previously described, this reagent is able to trifluoromethylate more acidic enolizable compounds.
Trifluoroacetamides from amino alcohols as nucleophilic trifluoromethylating reagents
Joubert, Jerome,Roussel, Solveig,Christophe, Carole,Billard, Thierry,Langlois, Bernard R.,Vidal, Thierry
, p. 3133 - 3136 (2007/10/03)
Both non-enolizable and enolizable carbonyl compounds underwent nucleophilic trifluoromethylation by a new family of cheap and efficient trifluoroacetamide reagents derived from vic-amino alcohols (see picture). From an ecological and an economic viewpoint these represent a promising alternative to other known trifluoromethylation reagents.
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.
