Palladium-catalyzed sequential alkylation-alkenylation reactions: application towards the synthesis of polyfunctionalized fused aromatic rings

The synthesis of polyfunctionalized fused aromatic carbo- and heterocycles from aryl iodides and bromoenoates via a tandem palladium-catalyzed aromatic substitution intramolecular Heck sequence is reported. Using Pd(OAc)2 and tri-2-furylphosphine in the presence of norbornene and Cs2CO3 in CH3CN at 85 °C gave a variety of functionalized bi- and tricyclic fused aromatic rings in good yield.