149846-93-5

Upstream product

• 943610-08-0 1,1-dichloro-3,3,3-trifluoro-2-tosyloxypropene 
• 100-52-7 benzaldehyde 
• 754-12-1 2,3,3,3-tetrafluoro-propene 
• 949112-27-0 (E)-2-chloro-4,4,4-trifluoro-1-phenylbut-2-en-1-ol 
• 102687-65-0 trans-1-chloro-3,3,3-trifluoropropene 
• 99728-16-2 (Z)-1-chloro-3,3,3-trifluoro-1-propene 
• 460-73-1 1,1,1,3,3-Pentafluoropropane 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 661-54-1 3,3,3-trifluoroprop-1-yne 
• 14856-86-1 (3,3,3-trifluoroprop-1-yn-1-yl)lithium 

Downstream Products

• 1140529-97-0 C₂₁H₂₃F₃O₇ 
• 1140530-12-6 C₁₀H₆ClF₃ 
• 1140530-13-7 3-chloro-4,4,4-trifluoro-1-phenylbuta-1,2-diene 
• 1140530-14-8 C₂₀H₁₂F₆O 
• 1147879-67-1 (E)-1,1,1-trifluoro-4-hydroxy-4-phenyl-2-triethylsilyl-2-butene 
• 956903-43-8 C₁₀H₁₀F₂O 
• 114192-88-0 (E)-4,4,4-trifluoro-1-phenylbut-2-en-1-one 
• 245543-77-5 2,3-dibromo-4,4,4-trifluoro-1-phenyl-butan-1-one 
• 801289-32-7 (E)-4,4,4-trifluoro-1-phenylbut-2-en-1-ol 
• 3108-34-7 (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one 

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.

HFO-1234yf as a CF3-Building Block: Synthesis and Chemistry of CF3-Ynones

Reaction of low cost, readily available 4th generation refrigerant gas 2,3,3,3-tetrafluoropropene (HFO-1234yf) with lithium diisopropylamide (LDA) leads to formation of lithium 3,3,3-trifluoropropynide, addition of which to a range of aldehydes formed CF3-alkynyl alcohol derivatives on multigram scale, which were oxidised using Dess–Martin periodinane (DMP) to give substituted CF3-ynones with minimal purification required. Michael-type additions of alcohol and amine nucleophiles to CF3-ynones are rapid and selective, affording a range of CF3-enone ethers and enaminones in excellent yields with high stereoselectivity for the Z-isomer. By analogous reactions with difunctional nucleophiles, a wide range of CF3-substituted pharmaceutically relevant heterocyclic structures can be accessed, exemplified in the simple synthesis of the anti-arthritis drug celecoxib from HFO-1234yf in just three steps.

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.

The preparation and cycloaddition reaction of 1-sulfonyl-1-trifluoromethyl allenes

A series of 1-sulfonyl-1-trifluoromethyl allenes were prepared for the first time from commercial available 2-bromo-3,3,3-trifluoropropene. Cycloaddition reaction of these trifluoromethylated allenes with nitrones occured readily under mild conditions, giving the corresponding trifluoromethylated isoxazolidines in high yields.

Iron-Catalyzed Thiocyclization for the Synthesis of Trifluoro-methylated Benzothiophenes by C-H Functionalization of Aryl Disulfides

An iron-catalyzed thiocyclization of propynols with aryl disulfides has been developed for the synthesis of trifluoromethylated benzothiophenes. The one-pot tandem reaction involves Meyer-Schuster -rearrangement of propynols and radical cyclization through C-H functionalization of aryl disulfides. A variety of 2-trifluoroacyl benzothiophenes were prepared in moderate to good yields with good functional-group tolerance.

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

Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-cata

Electronically promoted Payne rearrangement of 3-CF3-2,3- epoxyalcohols

(Chemical Equation Presented) Smooth and selective Payne rearrangement was achieved for the above types of epoxyalcohols with a CF3 group so as to form thermodynamically more stable alkoxides, where the strongly electron-withdrawing nature of this moiety played a significantly important role and was proved to overcome increased steric instability of epoxides from syn-E to anti-Z isomers.

Hydrofluorocarbon 245fa: A versatile new synthon in alkyne chemistry

The CFC replacement 1,1,1,3,3-pentafluoropropane (HFC 245fa) has been established as a convenient source of trifluoropropynyllithium under mild conditions; a range of novel and known trifluoropropynyl-containing systems has been prepared in a one-pot procedure.