434-64-0Relevant articles and documents
On the mechanism of the reaction of CF3 radicals with C6F5Cl in the temperature range 318-473 K
Nieto,Lane,Oexler
, p. 868 - 871 (1997)
The gas-phase reaction of CF3 radicals, generated by photolysis of perfluoroacetic anhydride, with C6F5Cl was studied in the temperature range 318-473 K and total pressures between 23 and 41 Torr. CF3 radicals react with C6F5Cl according to the following mechanism: CF3 + C6F5Cl ?kadd CF3C6F5Cl (1), (-1) CF3 + CF3C6F5Cl → CF3Cl + C6F5CF3 (2) 2CF3 →kc C2F6 (3) It was found that the addition reaction becomes reversible above 390 K. The addition rate parameters can be summarized in the following equation: log [(kadd/kc1/2)mol-1/2cm 3/2s-1/2] = (4.46±0.10)-(22.48±0.70)/θ where θ = 2.303 RTkJ mol-1 and kc is the recombination constant of CF3 radicals. A correlation between log(kadd/kc1/2) and the ionization potentials for 15 aromatic compounds was found. VCH Verlagsgesellschaft mbH, 1997.
A Key Intermediate in Copper-Mediated Arene Trifluoromethylation, [nBu4N][Cu(Ar)(CF3)3]: Synthesis, Characterization, and C(sp2)?CF3 Reductive Elimination
Lu, Zehai,Liu, He,Liu, Shihan,Leng, Xuebing,Lan, Yu,Shen, Qilong
supporting information, p. 8510 - 8514 (2019/05/22)
The synthesis, characterization, and C(sp2)?CF3 reductive elimination of stable aryl[tris(trifluoromethyl)]cuprate(III) complexes [nBu4N][Cu(Ar)(CF3)3] are described. Mechanistic investigations, including kinetic studies, studies of the effect of temperature, solvent, and the para substituent of the aryl group, as well as DFT calculations, suggest that the C(sp2)?CF3 reductive elimination proceeds through a concerted carbon–carbon bond-forming pathway.
Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes
Chu, Lingling,Qing, Feng-Ling
supporting information; experimental part, p. 1298 - 1304 (2012/02/16)
This article describes the copper-catalyzed oxidative trifluoromethylation of heteroarenes and highly electron-deficient arenes with CF 3SiMe3 through direct C-H activation. In the presence of catalyst Cu(OAc)2, ligand 1,10-phenanthroline and cobases tert-BuONa/NaOAc, oxidative trifluoromethylation of 1,3,4-oxadiazoles with CF3SiMe3 proceeded smoothly using either air or di-tert-butyl peroxide as an oxidant to give the corresponding trifluoromethylated 1,3,4-oxadiazoles in high yields. Di-tert-butyl peroxide was chosen as the suitable oxidant for oxidative trifluoromethylation of 1,3-azoles and perfluoroarenes. Cu(OH)2 and Ag2CO3 were the best catalyst and oxidant for direct oxidative trifluoromethyaltion of indoles. The optimum reaction conditions enable oxidative trifluoromethylation of a range of heteroarenes that bear numerous functional groups. The prepared trifluoromethylated heteroarenes are of importance in the areas of pharmaceuticals and agrochemicals. The preliminary mechanistic studies of these oxidative trifluoromethylations are also reported.
Skeletal transformations and fluorination of perfluoroalkylbenzenes in reactions with antimony pentafluoride
Karpov,Mezhenkova,Platonov
, p. 1176 - 1181 (2007/10/03)
Reaction of octafluorotoluene and perfluoro-m-xylene with tetrafluoroethylene in the presence of SbF5 yielded perfluorinated propyl-and 1,3-dipropylbenzene, and propyltoluene. The perfluoropropyl group of these compounds under the action of SbF5 at 200°C is transformed into perfluoroisopropyl or trifluoromethyl group. Polyfluoroalkylbenzenes in SbF5 medium undergo fluorinationb to afford perfluoro1-alkylcyclohexenes.
