113281-23-5

Upstream product

• 402-45-9 4-hydroxybenzotrifluoride 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 106-51-4 p-benzoquinone 
• 13636-88-9 3,3-bis(methylthio)-1-phenylprop-2-en-1-one 
• 120120-28-7 4-(triethylsiloxy)-4-(trifluoromethyl)-2,5-cyclohexadien-1-one 
• 75-46-7 trifluoromethan 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 

Relevant academic research and scientific papers

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

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.

1,3-Carbothiolation of 4-(trifluoromethyl)-p-quinols: A new access to functionalized (trifluoromethyl)arenes

A new strategy, the 1,3-carbothiolation/aromatization, for the synthesis of functionalized (trifluoromethyl)arenes has been developed that enables the regioselective introduction of two different functional groups onto an aromatic ring in the meta-position to each other in a single step.

Nucleophilic trifluoromethylation of carbonyl compounds and disulfides with trifluoromethane and silicon-containing bases

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.

Trifluoromethylation of carbonyl compounds

A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.

Gem-disubstituted cyclohexadienones and their production

Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts devoid of fluorine (e.g., LiN3, NaN3, KN3, NaCN KCN, CsCN, NaOH, KOH, K2 CO3, and Cs2 CO3). The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.

A New Method for Synthesis of Trifluoromethyl-Substituted Phenols and Anilines

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.

Clorous Acid Oxidation of Trifluoromethylphenols: Cyclopentenolones by Benzilic Acid Ring Contraction

The formation of 2-chloro-2-trifluoromethylcyclopentane-1,3-dione (1) in the chlorous acid oxidation of 2- and 3-trifluoromethylphenol is shown to proceed via decarboxylation of 5-chloro-1-hydroxy-4-oxo-5-trifluoromethylcyclopent-2-enecarboxylic acid (4), an isolable compound.