Oxidative Organic Transformations Photocatalyzed by NDI in Visible Light

In this work, we report the synthesis and photocatalytic properties of <i>N,N</i>-bis(<i>n</i>-hexyl)-2-bromo-6-(<i>n</i>-hexylamino)-1,4,5,8-naphthalenetetracarboxylic diimide photocatalyst, <b>NDI-PC</b>, in visible light. In the presence of air or oxidant, <b>NDI-PC</b> 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.