Radical-Induced Cycloaromatization: Routes to Fluoranthenes and Acephenanthrylenes

The cycloaromatization of easily-prepared arenediynes is an efficient route to fused aromatic systems, but the requirement of very high temperatures to induce this reaction limits both scalability and generality. We demonstrate that cycloaromatization can be induced by addition of a radical species to an arenediyne unit. Tethering this radical to the enediyne leads to the formation of larger fused systems, such as fluoranthenes and acephenanthrylenes, in a single step.