1744-46-3Relevant academic research and scientific papers
The solid complex Zn(CF3)Br·2DMF as an alternative reagent for the preparation of both, trifluoromethyl and pentafluoroethyl copper, CuCF3 and CuC2F5
Kremlev, Mikhail M.,Tyrra, Wieland,Mushta, Aleksej I.,Naumann, Dieter,Yagupolskii, Yurii L.
, p. 212 - 216 (2010)
Trifluoromethylcopper and pentafluoroethylcopper are prepared conveniently via the reaction of the solid complex Zn(CF3)Br·2DMF with copper(I) bromide in N,N-dimethylformamide. The reactions of both copper species with 2,4-dinitrochlorobenzene,
THE TRIFLUOROMETHYLATION OF CHLOROAROMATICS USING THE COPPER-CF2Br2-DIALKYLAMIDE REACTION SYSTEM
Clark, James H.,Denness, James E.,McClinton, Martin A.,Wynd, Andrew J.
, p. 411 - 426 (2007/10/02)
The in situ generation of CuCF3 from the reaction of copper, dibromodifluoromethane and either N,N-dimethylformamide or N,N-dimethylacetamide (Burton's reagent) has been used for the direct substitution of chlorine by CF3 in a number of aromatic substrates.Particular attention has been paid to the effects of ring substituents on the efficiency of reaction.
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.
