Palladium-catalyzed sequential alkylation - Alkenylation reactions and their application to the synthesis of fused aromatic rings

Article abstract of DOI:10.1021/jo0107296

The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)₂ (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs₂CO₃ (2 equiv), CH₃CN, reflux), bromoenoates react with aryl iodides bearing numerous substituents (F, Cl, CF₃, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.