Issue 54, 2019

Tris(dimethylamino)silylium ion: structure and reactivity of a dimeric silaguanidinium

Abstract

Although several strategies for the stabilization of silylium ions have been established, “π-stabilization” with directly attached π-donor heteroatoms at silicon has not been developed yet. Hydride abstraction from (Me2N)3SiH generates dicationic [(Me2N)3Si+]2 in solution and in the solid state – constituting the dimer of an elusive silaguanidinium ion. This compound can be synthesized on a gram scale and is compatible with common organic solvents. However, it readily undergoes spontaneous electrophilic silylation of electron-rich aromatic compounds or initiates a catalytic hydro-defluorination reaction.

Graphical abstract: Tris(dimethylamino)silylium ion: structure and reactivity of a dimeric silaguanidinium

Supplementary files

Article information

Article type
Communication
Submitted
10 May 2019
Accepted
11 Jun 2019
First published
12 Jun 2019

Chem. Commun., 2019,55, 7764-7767

Tris(dimethylamino)silylium ion: structure and reactivity of a dimeric silaguanidinium

N. Kramer, H. Wadepohl and L. Greb, Chem. Commun., 2019, 55, 7764 DOI: 10.1039/C9CC03625C

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