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Bis(perfluoropinacolato)silane: a neutral silane Lewis superacid activates Si-F bonds

Despite the earth abundance and easy availability of silicon, only few examples of isolable neutral silicon centered Lewis superacids are precedent in the literature. To approach the general drawbacks of limited solubility and unselective deactivation pathways, we introduce a Lewis superacid, based...

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Main Authors: Tschernuth, Florian (Author) , Thorwart, Thaddäus (Author) , Greb, Lutz (Author) , Hanusch, Franziska-Maria (Author) , Inoue, Shigeyoshi (Author)
Format: Article (Journal)
Language:English
Published: December 1, 2021
In: Angewandte Chemie. International edition
Year: 2021, Volume: 60, Issue: 49, Pages: 25799-25803
ISSN:1521-3773
DOI:10.1002/anie.202110980
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202110980
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202110980
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Author Notes:Florian S. Tschernuth, Thaddäus Thorwart, Lutz Greb, Franziska Hanusch, Shigeyoshi Inoue

MARC

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520 |a Despite the earth abundance and easy availability of silicon, only few examples of isolable neutral silicon centered Lewis superacids are precedent in the literature. To approach the general drawbacks of limited solubility and unselective deactivation pathways, we introduce a Lewis superacid, based on perfluorinated pinacol substituents. The compound is easily synthesized on a gram-scale as the corresponding acetonitrile mono-adduct 1⋅(MeCN) and was fully characterized, including single crystal X-ray diffraction analysis (SC-XRD) and state-of-the-art computations. Lewis acidity investigations by the Gutmann-Beckett method and fluoride abstraction experiments indicate a Lewis superacidic nature. The challenging Si−F bond activation of Et3SiF is realized and promising catalytic properties are demonstrated, consolidating the potential applicability of silicon centered Lewis acids in synthetic catalysis. 
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