772-62-3

Upstream product

• 591-50-4 iodobenzene 
• 63904-39-2 chloro-(3,3,3-trifluoro-prop-1-ynyl)-zinc 
• 2314-97-8 iodotrifluoromethane 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 115395-69-2 3-phenyl-2,2-dichloro-1,1,1-trifluoropropane 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 34091-69-5 (2-chloro-3,3,3-trifluoroprop-1-en-1-yl)benzene 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 145397-30-4 C₈H₂₁N₄PSi 
• 60504-00-9 3,3,3-trichloro-1-phenyl-propene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 536-74-3 phenylacetylene 
• 1058685-73-6 N,N-(dimethylamino)-S-phenyl-S-trifluoromethyloxosulfonium trifluoromethanesulfonate 
• 887144-97-0 Togni's reagent 

Downstream Products

• 718-65-0 3,3,3-Trifluor-1,1,2,2-tetrachlor-1-phenyl-propan 
• 712-47-0 1.2-Dibrom-2-trifluormethyl-1-phenyl-ethylen 
• 96256-50-7 1-methyl-4-phenyl-3-(trifluoromethyl)-1H-pyrazole 
• 96256-48-3 3-methyl-1-phenyl-5-(trifluoromethyl)-1H-pyrazole 
• 96256-49-4 1-Methyl-5-phenyl-4-trifluoromethyl-1H-pyrazole 
• 96256-51-8 1-methyl-4-phenyl-5-trifluoromethyl-1H-pyrazole 
• 96256-53-0 4-phenyl-3-(trifluoromethyl)-1H-pyrazole 
• 96256-52-9 3-Phenyl-4-trifluoromethyl-1H-pyrazole 
• 709-21-7 3,3,3-trifluoro-1-phenylpropan-1-one 
• 105995-06-0 C₁₅H₁₁F₃S 
• 105995-05-9 C₁₅H₁₁F₃S 
• 96256-60-9 1,4-Diphenyl-5-trifluoromethyl-1H-[1,2,3]triazole 
• 96256-59-6 1,5-diphenyl-4-(trifluoromethyl)-1,2,3-triazole 
• 105995-07-1 C₁₅H₁₁F₃O 

Relevant academic research and scientific papers

Synthesis of 2-trifluoromethyl-2-hydroxy-2H-chromenes via cyclization of (Z)-trifluoromethyl alkenyl triflates and salicylaldehydes

A new and efficient method for the synthesis of 2-trifluoromethyl-2-hydroxy-2H-chromenes was developed via intermolecular cyclization of (Z)-trifluoromethyl alkenyl triflates and salicylaldehydes. A series of 2-trifluoromethyl-2-hydroxy-2H-chromenes with aryl or alkyl groups at 3-position have been obtained in moderate to excellent yields. And a key intermediate, 3-phenyl-4-(pyrrolidin-1-yl)-2-(trifluoromethyl)chroman-2-ol (6), was isolated and fully characterized, which suggests that the elimination of pyrrolidine from this intermediate is the last step during the formation of 2-trifluoromethyl-2-hydroxy-2H-chromenes.

Solvated Nickel Complexes as Stoichiometric and Catalytic Perfluoroalkylation Agents**

The acetonitrile-solvated [(MeCN)Ni(C2F5)3]? was prepared in order to compare and contrast its reactivity with the known [(MeCN)Ni(CF3)3]? towards organic electrophiles. Both [(MeCN)Ni(CF3)3]? and [(MeCN)Ni(C2F5)3]? successfully react with aryl iodonium and diazonium salts as well as alkynyl iodonium salts to give fluoroalkylated organic products. Electrochemical analysis of [(MeCN)NiII(C2F5)3]? suggests that, upon electro-oxidation to [(MeCN)nNiIII(C2F5)3], reductive homolysis of a perfluoroethyl radical occurs, with the concomitant formation of [(MeCN)2NiII(C2F5)2]. Catalytic C?H trifluoromethylations of electron-rich arenes were successfully achieved using either [(MeCN)Ni(CF3)3]? or the related [Ni(CF3)4]2?. Stoichiometric reactions of the solvated nickel complexes reveal that “ligandless” nickel is exceptionally capable of serving as reservoir of CF3 groups under catalytically relevant conditions.

Synthesis of fluoroalkylated alkynes: Via visible-light photocatalysis

Fluoroalkylated alkynes, which are versatile building blocks for the synthesis of various biologically active organofluorine compounds, were synthesized from easily available alkynyl halides and fluoroalkyl halides by visible-light photocatalysis. Addition of fluoroalkyl radicals to alkynes and subsequent dehalogenation selectively yielded fluoroalkylated alkynes.

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Catalyst-free room-temperature iClick reaction of molybdenum(II) and tungsten(II) azide complexes with electron-poor alkynes: Structural preferences and kinetic studies

Two isostructural and isoelectronic group VI azide complexes of the general formula [M(η3-allyl)(N3)(bpy)(CO)2] with M = Mo, W and bpy = 2,2′-bipyridine were prepared and fully characterized, including X-ray structure analysis. Both reacted smoothly with electron-poor alkynes such as dimethyl acetylenedicarboxylate (DMAD) and 4,4,4-trifluoro-2-butynoic acid ethyl ester in a catalyst-free room-temperature iClick [3 + 2] cycloaddition reaction. Reaction with phenyl(trifluoromethyl)acetylene, on the other hand, did not lead to any product formation. X-ray structures of the four triazolate complexes isolated showed the monodentate ligand to be N2-coordinated in all cases, which requires a 1,2-shift of the nitrogen from the terminal azide to the triazolate cycloaddition product. On the other hand, a 19F NMR spectroscopic study of the reaction of the fluorinated alkyne with the tungsten azide complex at 27 °C allowed detection of the N1-coordinated intermediate. With this method, the second-order rate constant was determined as (7.3 ± 0.1) × 10-2 M-1 s-1, which compares favorably with that of first-generation compounds such as difluorocyclooctyne (DIFO) used in the strain-promoted azide-alkyne cycloaddition (SPAAC). In contrast, the reaction of the molybdenum analogue was too fast to be studied with NMR methods. Alternatively, solution IR studies revealed pseudo-first order rate constants of 0.4 to 6.5 × 10-3 s-1, which increased in the order of Mo > W and F3C-CC-COOEt > DMAD.

Copper(I)-Catalyzed Interrupted Click Reaction with TMSCF3: Synthesis of 5-Trifluoromethyl 1,2,3-Triazoles

We herein describe a Cu(I)-catalyzed interrupted click reaction, using (trifluoromethyl)trimethylsilane (TMSCF3) as a nucleophilic CF3 source, to synthesize 5-trifluoromethyl 1,2,3-triazoles in one step from readily available terminal alkynes and azides. The reaction shows complete regioselectivity, broad substrate scope, and good functional group tolerability. The application of the reaction has been demonstrated in the synthesis of a trifluoromethylated analog of antiepileptic drug rufinamide.

Fluoroform-Derived CuCF3 for Trifluoromethylation of Terminal and TMS-Protected Alkynes

An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.

Cyclic-Protected Hexafluoroacetone as an Air-Stable Liquid Reagent for Trifluoromethylations

An air-stable liquid trifluoromethylating reagent is readily synthesized from gaseous hexafluoroacetone and 2-methylproline on a gram scale. The reaction of the trifluoromethylating reagent with tert-butoxy cuprate K[Cu(OtBu)2] leads to the CuCF3in high yield. This species is directly formed from the tetrahedral cuprate intermediate through intramolecular migration of the trifluoromethyl group to copper. The CuCF3reagent prepared in situ by our method can be used for the trifluoromethylation of aryl iodides, arylboronic acids, and terminal alkynes in good to excellent yields, even on a gram scale. Furthermore, the CuC2F5reagent can be prepared in the same way, and this can be used in the pentafluoroethylation of arylboronic acids or aryl bromides in good to excellent yields.

Gold(I)-catalysed tandem cyclization of propargyl acetals and alkynes

To expand the understanding of the chemistry of propargyl acetals, their gold(I) catalysed cycloaddition reactions with alkynes have been investigated. We hereby report a novel tandem reaction that allows the construction of a new type of polysubstituted

Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3at room temperature

A novel Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3has been developed for the construction of Csp-CF3bond under mild conditions. This method proceeds smoothly at room temperature and shows a widely functional compatibility, providing a series of corresponding trifluoromethylated acetylenyl-containing aromatics in good yields.