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Angew Chem Int Ed Engl. 2016 Dec 23;55(52):16156-16160. doi: 10.1002/anie.201609096. Epub 2016 Nov 30.

The Tris(pentafluoroethyl)silanide Anion.

Author information

1
Universität Bielefeld, Fakultät für Chemie, Centrum für Molekulare Materialien, Universitätsstrasse 25, 33615, Bielefeld, Germany.

Abstract

Tris(pentafluoroethyl)silane, which is conveniently accessible by the treatment of Si(C2 F5 )3 X (X=Cl, Br) with Bu3 SnH, was successfully employed for hydrosilylation reactions. In the presence of a palladium catalyst, hydrosilylation of phenylacetylene with Si(C2 F5 )3 H affords the product of an α-addition whereas the reaction of trimethylsilylacetylene with the silane leads to the β-trans product. Tris(pentafluoroethyl)silane can be deprotonated by sterically demanding bases such as lithium diisopropylamide at low temperatures to give the corresponding silanide ion. The addition of crown ethers or cryptands to this highly reactive species enabled the isolation and characterization of salt-like tris(pentafluoroethyl)silanide at room temperature.

KEYWORDS:

fluorine; hydrosilylation; perfluoroalkyl compounds; silanes; silanides

PMID:
27902868
DOI:
10.1002/anie.201609096

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