313-16-6Relevant academic research and scientific papers
Simple Photo-Induced Trifluoromethylation of Aromatic Rings
Egami, Hiromichi,Ito, Yuta,Ide, Takafumi,Masuda, Shuya,Hamashima, Yoshitaka
, p. 2948 - 2953 (2018)
The trifluoromethylation of various aromatic compounds with Umemoto reagent II (2,8-difluoro-5-(trifluoromethyl)-5 H -dibenzo[ b, d ]thiophen-5-ium triflate) proceeded in moderate to good yields under simple photo-irradiation conditions without any cataly
5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives
Kuninobu, Yoichiro,Nishi, Mitsumi,Kanai, Motomu
, p. 8092 - 8100 (2016/09/09)
We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.
Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide
Kino, Tatsuhito,Nagase, Yu,Ohtsuka, Yuhki,Yamamoto, Kyoko,Uraguchi, Daisuke,Tokuhisa, Kenji,Yamakawa, Tetsu
experimental part, p. 98 - 105 (2010/03/03)
Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five-membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as reported in other radical trifluoromethylation previously.
Experimental and Computational Studies of Trifluoromethylation of Aromatic Amines by the System Trifluoroiodomethane-Zinc-Sulfur Dioxide
Strekowski, Lucjan,Hojjat, Maryam,Petterson, Steven E.,Kiselyov, Alexander S.
, p. 1413 - 1416 (2007/10/02)
Several trifluoromethyl-substituted aromatic and heteroaromatic amines have been obtained by the reactions of the corresponding amines with the title reagent system.Computational results provide rationalization for the observed regioselectivities and support a mechanism in which the electrophilic trifluoromethyl radicals interact with the aromatic ring at the sites with the greatest electron density of the HOMO orbitals, and then the resultant adducts are oxidized to cations.The products obtained are potential building blocks for a number of heterocyclic systems.
