573979-96-1

Upstream product

• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 10602-03-6 ethyl 4-ethynylbenzoate 
• 77152-08-0 trifluoromethylcopper(I) 
• 1580514-95-9 C₁₁H₉BF₃O₂^(1-)*K⁽¹⁺⁾ 
• 2926-29-6 Langlois reagent 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 672339-38-7 (Z)-2,3,3,3-tetrafluoro-1-iodoprop-1-ene 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 

Downstream Products

• 877458-03-2 Bu₃SnC(CF₃)C(CCCF₃)C₆H₄-CO₂Et-p 
• 1225288-99-2 3,5,6-tris(4-ethoxycarbonylphenyl)-1,2,4-tris(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF3]

A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.

Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed Hydroarylation and Subsequent Cadogan Cyclization

The copper-catalyzed hydroarylation of (trifluoromethyl)alkynes with (o-nitrophenyl)boronic acids selectively afforded trisubstituted (trifluoromethyl)alkenes bearing an o-nitrophenyl group. The obtained hydroarylation products were converted into 3-aryl-2-(trifluoromethyl)indoles in high yields via molybdenum-catalyzed Cadogan cyclization. Similarly, the hydroarylation product prepared from (o-nitrophenyl)(trifluoromethyl)alkyne and (p-anisyl)boronic acid also underwent Cadogan cyclization, albeit with a longer reaction time, affording the desired indole product in a high yield. (Figure presented.).

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.

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.

Selective synthesis of trisubstituted (trifluoromethyl)alkenes: Via ligand-free Cu-catalyzed syn hydroarylation, hydroalkenylation and hydroallylation of (trifluoromethyl)alkynes

In the presence of catalytic amounts of Cu(OAc)2, the hydroarylation of (trifluoromethyl)alkynes with arylboronic acids proceeded in MeOH at 28 °C to afford diverse β-(trifluoromethyl)styrenes. Moreover, the hydroalkenylation and hydroallylation of a (trifluoromethyl)alkyne using styryl- and allylboronates afforded trifluoromethylated 1,3- and 1,4-dienes.

Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent Dedicated to Professor Pierre Vogel on the occasion of his 70th birthday

Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates.

Copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids using (trifluoromethyl)trimethylsilane

Trifluoromethylated acetylenes and arenes are widely applicable in the synthesis of pharmaceuticals and agrochemicals. In 2010, our group has reported the copper-mediated oxidative trifluomethylation of terminal alkynes and aryl boronic acids. This method allows a wide range of functional group tolerant trifluoromethylated acetylenes and arenes to be easily prepared. After the preliminary mechanistic studies of the oxidative trifluoromethylation of terminal alkyne, an efficient copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids has been developed. The catalytic protocol is successfully achieved by adding both the substrate and a portion of CF3TMS slowly using a syringe pump to the reaction mixture.

An improved copper-mediated oxidative trifluoromethylation of terminal alkynes

An improved method for the efficient copper-mediated trifluoromethylation of terminal alkynes has been developed. This protocol highlights the convenient access to a variety of aryl-substituted trifluoromethylated alkynes by oxidative trifluoromethylation

Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3

An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me3SiCF3) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO2Et, -Br, and -NO2 were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful method to prepare trifluoromethylated acetylenes.

Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives

Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2· TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh 3)4, reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields.