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Chemistry. 2016 Nov 21;22(48):17460-17467. doi: 10.1002/chem.201603442. Epub 2016 Oct 25.

Synthesis of Functional Bis(pentafluoroethyl)silanes (C2 F5 )2 SiX2 , with X=H, F, Cl, Br, OPh, and O2 CCF3.

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Centrum für Molekulare Materialien, Fakultät für Chemie, Anorganische Chemie II, Universität Bielefeld, Universitätsstrasse 25, 33615, Bielefeld, Germany.
Merck KGaA, Frankfurter Straße 250, 64293, Darmstadt, Germany.


As recently shown, the introduction of pentafluoroethyl functionalities into silicon compounds is of general interest due to an enhanced Lewis acidity of the resulting species. By this means, the synthesis of previously inaccessible hypervalent silicon derivatives is enabled. While an easy access to tris(pentafluoroethyl)silanes has already been published, synthetic strategies for the selective preparation of bis derivatives are yet unknown. In this contribution, a convenient protocol for the synthesis of functional bis(pentafluoroethyl)silicon compounds is presented. These compounds represent precursors for the synthesis of pentafluoroethylated polysiloxanes. Furthermore, they prove to be resistant to oxonium cations, which is a key feature for the preparation of stable pentafluoroethylsilic acids. Treatment of dichlorodiphenoxysilane with in situ generated pentafluoroethyl lithium leads to the corresponding bis(pentafluoroethyl)silane in high yields. (C2 F5 )2 Si(OPh)2 serves as a starting material for further functionalized bis(pentafluoroethyl)silanes. These silanes have been isolated and their reactivity towards N bases studied. The pronounced Lewis acidity of the obtained compounds has been documented by the formation of octahedral adducts with nitrogen donors such as 1,10-phenanthroline and acetonitrile.


Lewis acids; fluorine; halogens; perfluoroalkyl; silicon


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