Amplifying Lewis Acidity by Oxidation: Leveraging the Redox-Activity of Bis(3,6-di-tert-butyl-catecholato)silane

Abstract

Bis(catecholato)silanes were showcased as strong Lewis acids, while their inherent redox activity remained unexplored in this context. In the present work, we study the oxidation of monomeric bis(3,6-di-tert-butyl-catecholato)silane (1), leading to the Lewis superacidic radicalic silylium ionradical 1•+ (FIA 784 kJ mol−1). Oxidation of 1 with [N(p-C6H4Br)3][B(C6F5)4] yielded [1][B(C6F5)4], displaying strong catalytic activity in the Friedel-Crafts-dimerization, hydrodeoxygenation and carbonyl-olefin-metathesis. It demonstrates how Lewis acidity can be amplified through oxidation without needing an add-on redox-active substituent. Instead, it synergizes the constraining effect of catecholates with their inherent redox non-innocence to unlock enhanced catalytic performance.

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Article information

Article type
Communication
Submitted
13 Nov 2024
Accepted
28 Nov 2024
First published
29 Nov 2024
This article is Open Access
Creative Commons BY license

Dalton Trans., 2024, Accepted Manuscript

Amplifying Lewis Acidity by Oxidation: Leveraging the Redox-Activity of Bis(3,6-di-tert-butyl-catecholato)silane

T. Thorwart, M. Schmitt and L. Greb, Dalton Trans., 2024, Accepted Manuscript , DOI: 10.1039/D4DT03176H

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