TY - JOUR
T1 - Bis(perfluoropinacolato)silane
T2 - A Neutral Silane Lewis Superacid Activates Si−F Bonds
AU - Tschernuth, Florian S.
AU - Thorwart, Thaddäus
AU - Greb, Lutz
AU - Hanusch, Franziska
AU - Inoue, Shigeyoshi
N1 - Publisher Copyright:
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH
PY - 2021/12/1
Y1 - 2021/12/1
N2 - 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.
AB - 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.
KW - Si-F activation
KW - main-group catalysis
KW - perfluoropinacol
KW - silicon Lewis superacid
KW - silicon mediated catalysis
UR - http://www.scopus.com/inward/record.url?scp=85118504408&partnerID=8YFLogxK
U2 - 10.1002/anie.202110980
DO - 10.1002/anie.202110980
M3 - Article
C2 - 34570964
AN - SCOPUS:85118504408
SN - 1433-7851
VL - 60
SP - 25799
EP - 25803
JO - Angewandte Chemie International Edition in English
JF - Angewandte Chemie International Edition in English
IS - 49
ER -