A series of epoxybenzo [k]fluoranthenes, epoxy-5Hbenzo[b]fluorenes, and their aza analogues have been accessed via palladium-catalyzed exo-selective [3 + 2] annulation between aryl halides and 7-oxa-and 7-azabenzonorbornadienes. The reaction is initiated by the oxidative addition of a carbon−halogen bond, with intramolecular C(sp 2 or sp 3 )−H activation being a key step. The enantioselective version of the reaction was also briefly explored.
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