80245-28-9Relevant academic research and scientific papers
Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex
Cantillo, David,Jud, Wolfgang,Kappe, C. Oliver,Maljuric, Snjezana
supporting information, (2019/10/08)
While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.
Introducing a new radical trifluoromethylation reagent
Sato, Azusa,Han, Jianlin,Ono, Taizo,Wzorek, Alicja,Ace?a, José Luis,Soloshonok, Vadim A.
supporting information, p. 5967 - 5970 (2015/03/30)
Perfluoro-3-ethyl-2,4-dimethyl-3-pentyl radical (PPFR) is a persistent radical stable at room temperature, but easily decomposes at 90 °C to produce a CF3 radical which is able to react with a variety of aromatic compounds to afford the corresponding trifluoromethyl derivatives, usually as mixtures of regioisomers in good to excellent overall yields.
Room-temperature base-free copper-catalyzed trifluoromethylation of organotrifluoroborates to trifluoromethylarenes
Huang, Yuanyuan,Fang, Xin,Lin, Xiaoxi,He, Weiming,Yuan, Yaofeng,Weng, Zhiqiang,Li, Huaifeng,Huang, Kuo-Wei
, p. 9949 - 9953,5 (2012/12/12)
An efficient room temperature copper-catalyzed trifluoromethylation of organotrifluoroborates under the base free condition using an electrophilic trifluoromethylating reagent is demonstrated. The corresponding trifluoromethylarenes were obtained in good to excellent yields and the reaction tolerates a wide range of functional groups.
Silver-mediated trifluoromethylation of arenes using TMSCF3
Ye, Yingda,Lee, Shin Hee,Sanford, Melanie S.
supporting information; experimental part, p. 5464 - 5467 (2011/12/05)
The silver-mediated C-H trifluoromethylation of aromatic substrates using TMSCF3 is described. The development, optimization, and scope of these transformations are reported. AgCF3 intermediates are proposed.
Phototransposition reactions of methyl-substituted benzotrifluorides: Proof of the role of trifluoromethyl-substituted carbon
DeCosta, Dayal,Pincock, James
, p. 9484 - 9487 (2007/10/03)
Irradiation in acetonitrile of any one of the six isomers of dimethylbenzotrifluoride 8 resulted in efficient photoisomerization to the others. The dominant processes in these phototransposition reactions divides the isomers into two triads. The first consists of 8-2,6 (2,6-dimethylbenzotrifluoride), 8-2,3, and 8-3,4; the second consists of 8-3,5, 8-2,4, and 8-2,5. Moreover, irradiation of 2,6-dideuterio-4-methylbenzotrifluoride 5-d2 resulted in formation of 5,6-dideuterio-3-methylbenzotrifluoride 6-d2. These observations demonstrate that it is the trifluoromethyl-substituted carbon that is the migratory one in these reactions.
A New Method for the Trifluoromethylation of Aromatics
Marhold, A.,Klauke, E.
, p. 281 - 292 (2007/10/02)
A new method is described for introducing a CF3-group, by a single-step synthesis, into aromatic compounds.This trifluoromethylation is done by means of a mixture consisting of HF/CCl4 and the aromatic compounds.The reaction is thought to be of a Friedel-Crafts type and limited to aromatics which are not substituted by electron withdrawing groups.
