Related Experiment Video
Updated: Feb 10, 2026

Activating Molecules, Ions, and Solid Particles with Acoustic Cavitation
Published on: April 11, 2014
Electrophilic Formylation of Arenes by Silylium Ion Mediated Activation of Carbon Monoxide
Lukas Omann1, Zheng-Wang Qu2, Elisabeth Irran1
1Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.
Abstract:
Arene-stabilized silylium ions react with carbon monoxide rather than carbon monoxide adducts of silylium ions reacting with arenes. This mechanism is supported by quantum-chemical calculations. Even sterically hindered mesitylene and electronically deactivated chlorobenzene engage in this electrophilic aromatic substitution. The silylium ion mediated formylation corresponds to Gattermann-Koch reactions promoted by strong Brønsted acids. The resulting silylcarboxonium ion of the arenecarbaldehyde was crystallographically characterized, for the first time revealing the molecular structure of this synthetically important intermediate.
More Related Videos
Related Concept Videos
The Carbon Cycle
Electrophiles
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
Common Ion Effect
Carbon Skeletons
Precipitation of Ions
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
Ion Channels
Ion channels are specialized integral membrane proteins on the plasma membrane that allow...

