264279-00-7

Upstream product

• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 123-11-5 4-methoxy-benzaldehyde 
• 102687-65-0 trans-1-chloro-3,3,3-trifluoropropene 

Downstream Products

• 1211006-86-8 C₁₁H₈BrF₃O 
• 1453496-06-4 C₂₀H₁₇F₃O₃ 
• 1453495-82-3 (3S,4S)-3-butyl-6-(4-methoxyphenyl)-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 89965-73-1 4,4,4-trifluoro-1-(4-methoxyphenyl)but-2-yn-1-one 
• 1184844-25-4 (E)-4,4,4-trifluoro-1-(4-methoxyphenyl)-2-buten-1-one 
• 1269758-76-0 (E)-3-deuterio-1-phenyl-4,4,4-trifluorobut-2-en-1-one 
• 1147880-08-7 (E)-4,4,4-trifluoro-1-(4-methoxyphenyl)-3-dimethylphenylsilyl-2-buten-1-ol 
• 1147880-09-8 C₁₉H₂₁F₃O₂Si 
• 1147880-00-9 (E)-1,1,1-trifluoro-4-hydroxy-4-(4-methoxyphenyl)-2-triethylsilyl-2-butene 
• 928658-49-5 4,4,4-trifluoro-1-(4-methoxyphenyl)-2-butynyl acetate 

Relevant academic research and scientific papers

Highly Enantioselective [3 + 2] Annulation of 3-Butynoates with β-Trifluoromethyl Enones Promoted by an Amine-Phosphine Binary Catalytic System

We report a highly enantioselective [3 + 2] annulation between 3-butynoates and β-trifluoromethyl enones, furnishing trifluoromethylated cyclopentenes with three contiguous stereogenic centers in good yields, high diastereoselectivities, and excellent enantioselectivities. A unique catalytic system consisting of a simple amine and a chiral phosphine was devised, and the synergistic play of Lewis basic amine and phosphine was crucial for alkyne isomerization and subsequent cyclization. The protocol disclosed herein allows facile activation of 3-butynoates in phosphine-mediated asymmetric transformations.

A Remarkable Influence of a Trifluoromethyl Group on the Reactions of β-Mercaptoalcohols with Fluorinated α-Bromoenones

Isomeric fluorinated α-bromoenones react with dinucleophilic β-mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S-heterocycles or non-cyclic products were obtained. With 3-bromo-1,1,1-trifluorobut-3-en-2-ones derivatives of 1,4-oxathianes were formed, but isomeric 2-bromo-4,4,4-trifluorobut-2-en-1-ones yielded 1,3-oxathiolanes or non-cyclic sulfides. The thia-Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.

Highly regio- and stereoselective hydrosilylation of β-fluoroalkylated α,β-unsaturated ketones

Treatment of β-fluoroalkylated α,β-unsaturated ketones with 10.2 equiv of triethylsilane in the presence of 3 mol% of Co2(CO)8 in dichloroethane at the reflux temperature for 4 h gave 1,4-hydrosilylated adducts in a highly regio- and

Stereospecific asymmetric N-heterocyclic carbene (NHC)-catalyzed redox synthesis of trifluoromethyl dihydropyranones and mechanistic insights

N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of α-aroyloxyaldehydes with β-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-β- trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.

Unusual behavior of the anionic species from (E)-1-chloro-3,3,3- trifluoropropene(HCFC-1233t)

(E)-1-Chloro-3,3,3-trifluoropropene was smoothly deprotonated by MeLi at the position β to the CF3 group, and exclusive formation of propargylic alcohols was observed by addition of appropriate carbonyl compounds as long as up to 1.6 equiv. of

Synthesis of 3-Trifluoroethylfurans by Palladium-Catalyzed Cyclization-Isomerization of (Z)-2-Alkynyl-3-trifluoromethyl Allylic Alcohols

Hydroiodonation of trifluoromethyl propargylic alcohols 1 regio- and stereoselectively produce (Z)-2-iodo-3-trifluoromethyl allylic alcohols 2. (Z)-2-Alkynyl-3-trifluoromethyl allylic alcohols 5, available through Pd(PPh3)4-mediated coupling of 2 and terminal alkynes 4, cyclize and subsequently isomerize to 3-trifluoroethylfurans 6 upon catalysis under PdCl2(CH3CN)2 in THF at 5-10°C.