- Stable but reactive perfluoroalkylzinc reagents: Application in ligand-free copper-catalyzed perfluoroalkylation of aryl iodides
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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.
- Aikawa, Kohsuke,Nakamura, Yuzo,Yokota, Yuki,Toya, Wataru,Mikami, Koichi
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- Syntheses and UV-visible spectroscopic properties of new 'fluorophilic' fluorine-and perfluoroalkyl-substituted solvatochromic pyridinium N-phenolate betaine dyes
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Syntheses and negative solvatochromism of three new 'fluorophilic' fluorine- and perfluoroalkyl- substituted pyridinium N-phenolate betaine dyes 3-5 are described in order to obtain new zwitterionic dyes which should be less basic and better soluble in perfluorinated solvents than the solvatochromic standard betaine dyes 1 and 2, used to establish an empirical scale of solvent polarity, called the ET (30) or ETN scale. The new betaine dyes 3-5 were designed to allow an extension of the existing ET (30) scale to new solvents. Copyright
- Reichardt, Christian,Eschner, Michael,Schaefer, Gerhard
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p. 737 - 751
(2007/10/03)
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- POLYFLUOROALKYLATION OF BROMOAROMATIC COMPOUNDS VIA PERFLUOROALKYLCOPPER INTERMEDIATES
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Cross coupling reactions between various perfluoroalkyl iodides, copper and mono and dibromobenzenes, as well as mono and dibromobenzenes containing functional groups e.g., OH, CO2H, CO2R, NO2, NH2, OCH3 and C(O)CH3 have produced perfluoroalkyl substituted aromatic compounds in good to excellent yields.From certain bromo arenes, by-products were obtained, indicating competing reactions.These reactions may be due to the slower rate of cross coupling between a carbon-bromine bond and the perfluoroalkylcopper intermediate as compared to the cross coupling reaction involving a carbon-iodine bond with the perfluoroalkylcopper intermediate.
- Chen, Grace J.,Tamborski, Christ
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p. 207 - 228
(2007/10/02)
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