1300746-85-3Relevant academic research and scientific papers
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.
A general, regiospecific synthetic route to perfluoroalkylated arenes via arenediazonium salts with RFCu(CH3CN) complexes
Jiang, Dong-Fang,Liu, Chao,Guo, Yong,Xiao, Ji-Chang,Chen, Qing-Yun
supporting information, p. 6303 - 6309 (2015/03/30)
A mild method of converting arylamines into perfluoroalkylated arenes is described. Relatively stable RFCu(CH3CN) complexes are used as perfluoroalkylating agents, which react smoothly with arenediazonium salts to produce various perfluoroalkylarenes in good yields. Based on the results of clock trapping experiments with diallyl ether, a radical process might be involved in the reaction.
FLUOROALKYLATION METHODS AND REAGENTS
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Page/Page column 7; 37-38, (2012/03/11)
A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.
A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuRF]
Litvinas, Nichole D.,Fier, Patrick S.,Hartwig, John F.
, p. 536 - 539 (2012/02/16)
A versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuRF]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF3] is now commercially available and has been prepared on 20g scale. Copyright
A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides
Morimoto, Hiroyuki,Tsubogo, Tetsu,Litvinas, Nichole D.,Hartwig, John F.
supporting information; experimental part, p. 3793 - 3798 (2011/05/15)
(Chemical Presented) Well compatible: The trifluoromethylations and perfluoroalkylations of aryl iodides and some aryl bromides with trifluoromethyl and perfluoroalkylcopper(I) phenanthroline complexes occur with broad scope at 25-50 8C (see scheme). The trifluoromethyl complex is prepared from inexpensive reagents and can be used in situ or isolated. The reactions tolerate a range of substituents and also occur with heteroaromatic systems.
