Issue 44, 2023

Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group

Abstract

Silyl chlorides are highly valuable and popular reagents for the protection of alcohols. In this edge article we introduce a photocleavable alcohol protecting group on the basis of acyl silanes. To achieve this, acylchlorosilanes that represent a new class of acylsilanes were developed. They can be easily synthesized in a concise sequence of three steps in high overall yield. Alcohol silyl protection takes place under established mild conditions, akin to those associated with classical silicon-based protecting groups. The removal of the Si-group is achieved at room temperature through exposure to visible light (456 nm) in methanol. We demonstrate a broad spectrum of substrates with remarkable tolerance toward diverse functional groups, highlighting a substantial level of orthogonality with respect to other protecting groups. Furthermore, we showcase the robustness of this approach against various transformations.

Graphical abstract: Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group

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Article information

Article type
Edge Article
Submitted
21 sep. 2023
Accepted
23 okt. 2023
First published
25 okt. 2023
This article is Open Access

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

Chem. Sci., 2023,14, 12615-12620

Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group

F. Lind, K. Markelov and A. Studer, Chem. Sci., 2023, 14, 12615 DOI: 10.1039/D3SC04975B

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