Palladium-catalyzed sequential alkylation-alkenylation reactions.  Application to the synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines. 
The synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines from aryl iodides and bromoenoates is described.  This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence.  Under the reaction conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20 mol %), norbornene (2 equiv), Cs(2)CO(3) (2 equiv), CH(3)CN, 85 degrees C), moderate to excellent yields of benzoxepines bearing numerous substituents (Me, F, Cl, etc.)  are obtained.