Deoxygenative Z-selective olefination of aliphatic alcohols

10 September 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Alcohols are one of the most abundant functional groups in commercially available materials and biologically active compounds. Herein, we report a mild photocatalytic method for the unprecedent deoxygenative Z-selective olefination of aliphatic alcohols. Key to this methodology is the dual role of a phenothiazine photocatalyst, which enables the desired cross-coupling and promotes in-situ E to Z isomerization of the cross-coupled olefin product. This protocol is distin-guished by its wide substrate scope and broad applicability, even in the context of pharmaceuticals and saccharides. Given the mild and water-compatible conditions, our chemistry can also be utilized to functionalize DNA headpieces with saccharides for DELs applications.

Keywords

alcohols
photocatalysis
synthesis
DELs

Supplementary materials

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Details of all experimental methods, characterization and mechanistic studies
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