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Cleavage of Unactivated Si−C(sp 3 ) Bonds with Reed's Carborane Acids: Formation of Known and Unknown Silylium Ions
Author(s) -
Wu Qian,
Qu ZhengWang,
Omann Lukas,
Irran Elisabeth,
Klare Hendrik F. T.,
Oestreich Martin
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201805637
Subject(s) - cleavage (geology) , ion , chemistry , alkyl , bond cleavage , carborane , inert , proton , medicinal chemistry , polymer chemistry , stereochemistry , organic chemistry , materials science , catalysis , physics , quantum mechanics , fracture (geology) , composite material
An efficient method for the benzenium‐ion‐mediated cleavage of inert Si−C(sp 3 ) bonds is reported. Various tetraalkylsilanes can thus be converted into the corresponding counteranion‐stabilized silylium ions. The reaction is chemoselective in the case of hexamethyldisilane. Computations reveal a mechanism with backside attack of the proton at one of the alkyl groups. Several activated Si−C(sp n ) bonds ( n =3–1) react equally well, and the procedure can be extended to the generation of stannylium ions.