Photocatalytic Cyanoalkyloxygenation and Cyanoalkylamination of Alkenes Using Cyclobutanone Oximes as Bifunctional Reagents

In this paper, we propose a photocatalytic strategy for the intermolecular dual functionalization of alkenes, employing N-O bifunctional reagents with high atom efficiency. Through the use of cyclobutanone oximes as dual-function precursors, which generate both distal cyano-substituted alkyl radicals and internal O-nucleophiles, this strategy facilitates the chemoselective cyanopropylation of olefins while simultaneously incorporating additional functional groups. This methodology provides straightforward access to a diverse array of doubly functionalized cyanoalkyl products via cyanoalkyloxygenation and cyanoalkylamination. Mechanistic analysis indicates that the selective interaction between radical and ionic pathways effectively establishes a unified platform for the dual functionalization of olefins.