Transition-metal and photocatalyst-free oxidative cleavage of aryl alkynes with PIDA/iminoiodinanes in visible light.

We report a transition-metal and photocatalyst-free method for the oxidative cleavage of aryl alkynes using phenyliodine diacetate (PIDA) and iminoiodinane in visible light. A variety of terminal and internal aryl alkynes afford aryl ketones in moderate yields under ambient conditions. Mechanistic studies suggest iminoiodinane serves as a nitrogen radical source and an arylating agent that undergoes aryl group migration.