Photocatalytic deoxygenative Z-selective olefination of aliphatic alcohols.

Abstract

Alcohols are one of the most abundant functional groups in commercially available materials and biologically active compounds. Herein, we report a metal-free photocatalytic method for the deoxygenative Z-selective olefination of aliphatic alcohols. Key to this methodology is the radical olefination and isomerization of unstabilized open-shell species generated in situ by a catalytic reductive scission of benzoate esters. These processes are simultaneously orchestrated by a single phenothiazine photocatalyst via singlet and triplet excited states. Our protocol is distinguished 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 for DELs applications.