30287-26-4Relevant academic research and scientific papers
BIS(TRIFLUOROMETHYL)ZINC DMPU COMPLEX, MANUFACTURING METHOD THEREOF AND MANUFACTURING METHOD OF TRIFLUOROMETHYL GROUP-CONTAINING COMPOUND USING THE SAME
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Paragraph 0027-0029, (2018/11/22)
PROBLEM TO BE SOLVED: To provide a bis(trifluoromethyl)zinc DMPU complex stable under room temperature and useful as a reaction reagent, a manufacturing method thereof and a manufacturing method of a trifluoromethyl group-containing compound using the same. SOLUTION: A method of obtaining a trifluoromethyl group-containing compound by reacting with a substituted aromatic iodide under a copper (I) catalyst after obtaining a bis(fluoromethyl)zinc DMPU complex represented by the formula (1) (CF3)2Zn (DMPU)2 (1), where DMPU represents N,N'-dimethyl propylene urea, by reacting dialkyl zinc, trifluoromethyl halide and N,N'-dimethyl propylene urea in an organic solvent, then filtration or solvent leaving removal of precipitate. COPYRIGHT: (C)2015,JPOandINPIT
Stable but reactive perfluoroalkylzinc reagents: Application in ligand-free copper-catalyzed perfluoroalkylation of aryl iodides
Aikawa, Kohsuke,Nakamura, Yuzo,Yokota, Yuki,Toya, Wataru,Mikami, Koichi
supporting information, p. 96 - 100 (2015/02/05)
The aromatic perfluoroalkylation catalyzed by a copper(I) salt with bis(perfluoroalkyl)zinc reagents Zn(RF)2(DMPU)2, which were prepared and then isolated as a stable white powder from perfluoroalkyl iodide and diethylzinc, was accomplished to provide the perfluoroalkylated products in good-to-excellent yields. The advantages of this reliable and practical catalytic reaction are 1) airstable and easy-to-handle bis(perfluoroalkyl)zinc reagents can be utilized, 2) the reagent is reactive and hence the operation without activators and ligands is simple, and 3) not only trifluoromethylation but also perfluoroalkylation can be attained.
Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
Nakamura, Yuzo,Fujiu, Motohiro,Murase, Tatsuya,Itoh, Yoshimitsu,Serizawa, Hiroki,Aikawa, Kohsuke,Mikami, Koichi
, p. 2404 - 2409 (2014/01/06)
The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing th
Me3SiCF3/AgF/Cu - A new reagents combination for selective trifluoromethylation of various organic halides by trifluoromethylcopper, CuCF3
Kremlev, Mikhail M.,Mushta, Aleksej I.,Tyrra, Wieland,Yagupolskii, Yurii L.,Naumann, Dieter,M?ller, Angela
experimental part, p. 67 - 71 (2012/03/10)
An alternative copper halide-free route to obtain highly reactive trifluoromethylcopper species has been developed via the reaction of silver fluoride and trimethyl(trifluoromethyl)silane followed by a redox transmetallation with elemental copper. The composition of the reactive intermediate was investigated by means of UV/Vis/NIR, ESR, 19F NMR spectroscopy and ESI mass spectrometry. "Trifluoromethylcopper" prepared by the oxidative transmetallation route exhibits excellent reactivity and selectivity in substitutions of iodine or bromine bond to aromatic or heterocyclic compounds for trifluoromethyl groups without any additional catalyst.
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.
experimental part, p. 212 - 216 (2010/04/30)
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,
Potassium 3-oxa-ω-fluorosulfonylperfluoropentanoate (FO2SCF2CF2OCF2CO2K), a low-temperature trifluoromethylating agent for organic halides; its α-carbon-oxygen bond fragmentation
Long, Zheng-Yu,Duan, Jian-Xin,Lin, Yuan-Bin,Guo, Cai-Yun,Chen, Qing-Yun
, p. 177 - 181 (2007/10/03)
The trifluoromethylation of organic halides with FO2SCF2CF2OCF2CO2K (1) in DMF can be accomplished at 45 °C which is advantageous for thermally sensitive substrates. α-Carbon-oxygen bond fragmentation of 1 and the related β-carbon-oxygen bond scission are discussed.
Synthesis of trifluoromethyl aryl derivatives via difluorocarbene precursors and nitro-substituted aryl chlorides
Duan, Jian-Xing,Su, De-Bao,Wu, Jian-Ping,Chen, Qing-Yun
, p. 167 - 170 (2007/10/02)
Treatment of aryl chlorides containing electron-withdrawing proups with methyl fluorosulfonyl difluoroacetate or methyl halodifluoroacetate in the presence of potassium fluoride and copper iodide gave the corresponding trifluoromethyl derivatives in moderate to high yields.
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.
THE EFFECT OF CHARCOAL ON THE TRIFLUOROMETHYLATION OF ARYL CHLORIDES USING BURTON'S REAGENT
Clark, James H.,McClinton, Martin A.,Jones, Craig W.,Landon, Philip,Bishop, D.,Blade, R. J.
, p. 2133 - 2136 (2007/10/02)
The reactivity of the trifluoromethylating system copper-dibromodifluoromethane-N,N-dimethylacetamide towards aryl chlorides can be enhanced by the addition of charcoal.
The Direct Trifluoromethylation of Aryl Chlorides using Burton's Reagent
Clark, James H.,McClinton, Martin A.,Blade, Robert J.
, p. 638 - 639 (2007/10/02)
The copper-dibromodifluoromethane-N,N-dimethylacetamide reaction system trifluoromethylates electronically activated aryl chlorides possessing ortho groups capable of interacting with the metal.
