- Nucleophilic tetrafluoroethylation employing in situ formed organomagnesium reagents
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Tetrafluoroalkyl bromides are metalated with equimolar iPrMgCl·LiCl (Turbo Grignard) to form organomagnesium compounds which are stable at low temperatures and react with various electrophiles (aldehydes, ketones, CO2, cyclic sulfate and sulfamidate, N-sulfonylimines, nitrone, chlorophosphate, nonaflyl azide) to afford novel functionalized tetrafluoroethylene-containing products. Ease of operation, excellent selectivity, high nucleophilicity, and enhanced stability of the reactive species together with a broad substrate scope comprise a highly attractive nucleophilic tetrafluoroethylation protocol affording unique synthetic building blocks.
- Budinská, Alena,Václavík, Ji?í,Matou?ek, Václav,Beier, Petr
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supporting information
p. 5844 - 5847
(2016/11/29)
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- Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones
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Global interest in the "CF2CF2" building blocks (tetrafluoroethylene, tetrafluoroethyl) is still rather marginal. One of the main reasons is the lack of efficient and selective tetrafluoroethylation reagents. In this context, we pres
- Václavík, Ji?í,Chernykh, Yana,Jurásek, Bronislav,Beier, Petr
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- An efficient preparation of new sulfonyl fluorides and lithium sulfonates
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(Formula Presented) An efficient preparation of several polyfluoroalkanesulfonyl fluorides is reported. This method, based on the synthesis of polyfluoroalkyl trimethyl silanes (precursors of polyfluoroalkylsulfinates) as intermediates, allows the successive transformations to be carried out in one pot. Moreover, these sulfonyl fluorides can be obtained from the corresponding sulfinates by electrophilic fluorination. This original approach avoids isolation and purification of some thermally or hydrolytically unstable intermediates. A series of new sulfonyl fluorides have been thus prepared from halogenodifluoromethylated precursors RCF2X (X = F, Br; R = ArC(O), ArS(O)n(CF2) m; n = 0, 1, 2; m = 1, 2) and have been transformed into the corresponding lithium sulfonates, which have potential applications as electrolytes for lithium batteries.
- Toulgoat, Fabien,Langlois, Bernard R.,Medebielle, Maurice,Sanchez, Jean-Yves
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p. 9046 - 9052
(2008/03/27)
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- CONDENSATION OF 1,2-DIBROMOTETRAFLUOROETHANE WITH VARIOUS POTASSIUM THIOPHENOXIDES AND PHENOXIDES
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BrCF2CF2Br reacts easily with various potassium thiophenoxides and phenoxides to give respectively 2-bromo tetrafluoroethyl thioethers and ethers.The lipophilicity of C6H5SCF2CF2Br and C6H5OCF2CF2Br is measured and compared with that of the well known C6H5SCF2CF2H and C6H5OCF2CF2H.
- Rico, I.,Wakselman, C.
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p. 759 - 764
(2007/10/02)
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