A three-component coupling reaction of organic halides with oxabicyclic alkene and terminal alkynes was catalyzed by a palladium complex and phase transfer agent in the presence of aqueous NaOH. The reaction gave a series of 5,6-disubstituated 7-oxabenzonorbornene derivatives in good yields . The disubstituted products from oxabenzonorbornadiene can be readily converted to polyaromatic hydrocarbons via a Lewis acid mediated deoxyaromatization reaction.
