65715-21-1Relevant 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.
Studies on Organic Fluorine Compounds. Part 27. Abnormal Reactions in the Trifluoromethylation of Aromatic Compounds with Trifluoromethyl Iodide and Copper Powder
Kobayashi, Yoshiro,Kumadaki, Itsumaro
, p. 661 - 664 (2007/10/02)
Reaction of 3-bromobenzofuran with trifluoromethyl iodide and copper powder in pyridine gave 2-(trifluoromethyl)-, 2- and 3-(pentafluoroethyl)-, and 2,3-bis(trifluoromethyl)-benzofuran, as well as the expected product, 3-(trifluoromethyl)benzofuran.Bromoanisole also gave (trifluoromethyl)anisole and (pentafluoroethyl)anisole, but introduction of the perfluoroalkyl group occurred at the position originally occupied by the bromine.Formation of pentafluoroethyl compounds is explained by decomposition of trifluoromethylcopper to cuprous fluoride and difluorocarbene, which can then react with a further molecule of trifluoromethylcopper to form pentafluoroethylcopper.This then reacts with aryl halide to give pentafluoroethyl compounds.Perfluoroalkylcopper is thermally cleaved to perfluoroalkyl radical, which then reacts with pyridine to give perfluoroalkylpyridines.This mechanism must be involved in the formation of 2,3-bis(trifluoromethyl)benzofuran.Introduction of a perfluoroalkyl group to the position originally unoccupied with halogen might be due to the rather localized double bond in benzofuran.
