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. 2018 Jul 16;57(29):9176-9179.
doi: 10.1002/anie.201805637. Epub 2018 Jun 19.

Cleavage of Unactivated Si-C(sp3 ) Bonds with Reed's Carborane Acids: Formation of Known and Unknown Silylium Ions

Qian Wu  1 , Zheng-Wang Qu  2 , Lukas Omann  1 , Elisabeth Irran  1 , Hendrik F T Klare  1 , Martin Oestreich  1
Affiliations

Cleavage of Unactivated Si-C(sp3 ) Bonds with Reed's Carborane Acids: Formation of Known and Unknown Silylium Ions

Qian Wu et al. Angew Chem Int Ed Engl. .

Abstract

An efficient method for the benzenium-ion-mediated cleavage of inert Si-C(sp3 ) 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(spn ) bonds (n=3-1) react equally well, and the procedure can be extended to the generation of stannylium ions.

Keywords: Brønsted acids; carboranes; density functional calculations; protonation; silylium ions.

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