Issue 22, 2025

Catalytic alkoxysilylation of C–H bonds with tert-butyl-substituted alkoxysilyldiazenes

Abstract

Organoalkoxysilanes (e.g. R–SiMe3−n(OR′)n, 1 ≤ n ≤ 3 with R = alkyl or aryl) have found various applications in synthetic chemistry and materials science because the silicon-bound alkoxy groups provide unique opportunities for further derivatization and transformations. Among the few catalytic strategies that allow the direct and intermolecular introduction of an alkoxysilyl unit onto an organic substrate, the alkoxysilylation of unactivated C–H bonds has barely been achieved despite its synthetic potential and the atom-economy it conveys. In particular, a catalytic and transition metal-free C–H silylation protocol towards this class of organosilicon compounds has yet to be reported. We herein describe the first general alkoxysilylation of (hetero)arene C(sp2)–H and benzylic C(sp3)–H bonds under ambient, transition metal-free conditions using newly-prepared tert-butyl-substituted alkoxysilyldiazenes (tBu–N[double bond, length as m-dash]N–SiMe3−n(OR′)n, 1 ≤ n ≤ 3 with R′ = Et, iPr or tBu) as silylating reagents and tBuOK as catalytic promoter.

Graphical abstract: Catalytic alkoxysilylation of C–H bonds with tert-butyl-substituted alkoxysilyldiazenes

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Article information

Article type
Edge Article
Submitted
16 Mar 2025
Accepted
23 Apr 2025
First published
24 Apr 2025
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2025,16, 9794-9801

Catalytic alkoxysilylation of C–H bonds with tert-butyl-substituted alkoxysilyldiazenes

L. Saadi, L. Valade and C. Chauvier, Chem. Sci., 2025, 16, 9794 DOI: 10.1039/D5SC02059J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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