208331-49-1

Upstream product

• 75-46-7 trifluoromethan 
• 1586-73-8 tris(trimethylsilyl)amine 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 497937-77-6 N-trifluoroacetyl-O-trimethylsilylephedrine 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 94-41-7 benzalacetophenone 
• 497937-79-8 N-trifluoromethanesulfinyl-O-trimethylsilylephedrine 
• 289706-46-3 4-[2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl]morpholine 

Downstream Products

• 208331-48-0 1-(trans)-phenylethenyl-1-phenyl-trifluoromethylcarbinol 

Relevant academic research and scientific papers

MgCl2-catalyzed trifluoromethylation of carbonyl compounds using (trifluoromethyl)trimethylsilane as the trifluoromethylating agent

Using (trifluoromethyl)trimethylsilane (TMSCF3) as the trifluoromethylating agent, MgCl2-catalyzed trifluoromethylation of carbonyl compounds proceeded readily at room temperature. In the presence of 10 mol% of MgCl2, a variety of carbonyl substrates such as aliphatic/aromatic aldehydes, acyclic/cyclic ketones and esters could be trifluoromethylated in DMF, giving the corresponding trimethylsilyl ethers (ketals) in up to 93% isolated yields. Trifluoromethylketones could be readily obtained after hydrolysis of the trimethylsilyl ketals. The reactions could tolerate air and moisture, and the use of oxygen and moisture-free conditions was not required.

Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates

The first enantioenriched synthesis of 1,1,3-trisubstituted (trifluoromethyl)indene derivatives, bearing a quaternary stereogenic carbon center, is reported using a simple chiral sulfinamide phosphine-catalyzed asymmetric allylic alkylation of a mixture of indenes with Morita-Baylis-Hillman carbonates. The resulting derivatives can serve as a valuable synthetic building block for some drugs and natural products. Broad substrate scope and high regio- and enantioselectivity of this reaction were particularly remarkable.

Acid-promoted cyclization of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-oles and their TMS-ethers into CF3-indenes

2,4-Diaryl-1,1,1-trifluorobut-3-en-2-oles and their TMS-ethers in H2SO4 at room temperature in just 2 min are quantitatively cyclized into 1-aryl-3-trifluoromethyl-1H-indenes. The reaction proceeds through an intermediate formation o

Tetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag

Tetraarylphosphonium inner-salts (TAPIS) have been designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst has been successfully applied in Michael addition, cyanation and trifluoromethylation reactions.

TTMPP-catalyzed trifluoromethylation of carbonyl compounds and imines with trifluoromethylsilane

A highly basic phosphine, tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP), catalyzes trifluoromethylation using trifluoromethyltrimethylsilane to give the corresponding trifluoromethylated products in good to high yields, with both carbonyl compounds and im

Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and imines with (perfluoroalkyl)trimethylsilane

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.

Lithium acetate-catalyzed trifluoromethylation of carbonyl compounds with (Trifluoromethyl)trimethylsilane

Trifluoromethylation of various aldehydes and ketones with (trifluoromethyl)trimethylsilane in the presence of a catalytic amount of a Lewis base such as lithium acetate proceeded smoothly to afford the corresponding trifluoromethylated adducts in good to

Trifluoromethanesulfinamide from ephedrine: A more efficient trifluoromethylating reagent

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

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

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.