Oxidative Organic Transformations Photocatalyzed by NDI in Visible Light.

In this work, we report the synthesis and photocatalytic properties of N,N -bis( n -hexyl)-2-bromo-6-( n -hexylamino)-1,4,5,8-naphthalenetetracarboxylic diimide photocatalyst, NDI-PC , in visible light. In the presence of air or oxidant, NDI-PC efficiently enables multiple photooxygenations of isoquinolines, thiocyanation of phenylimidazopyridines, functionalization of quinolinones by allowing regioselective installation of an SCN, SeCN, SPh, SePh, Cl, Br, or I group at the C-3 position, and isomerization of alkenes. Mechanistic investigations suggest an oxidative photoredox process for oxygenation and C-H functionalization, while isomerization is believed to proceed through a photosensitization pathway.