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

SUBMITTER: Lind F 

PROVIDER: S-EPMC10646889 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature