Carbocyclization of aromatic iodides, bicyclic alkenes, and benzynes involving a palladium-catalyzed C-H bond activation as a key step.

A facile palladium-catalyzed carbocyclization reaction of aromatic iodides, bicyclic alkenes (norbornadiene, norbornene and oxabenzonorbornadiene), and benzynes to furnish various annulated 9,10-dihydrophenanthrene derivatives is described. The carbocyclization products from oxabenzonorbornadiene were further converted to polyaromatic hydrocarbons via a Lewis acid mediated deoxyaromatization reaction. [reaction: see text].