(E)-beta-Bromostyrene [(E)-2] reacts with norbornene (1a) or dicyclopentadiene (1b) in the presence of Pd(OAc)(2), K2CO3, and nBu(4)NBr in DMF to yield a mixture of the 2:1 coupling products 4 and 5, while (Z)-beta-bromostyrene [(2)-2] gives exclusively 5. Under analogous conditions, (Z)-3-iodoacryclic acid (6) reacts with norbornene (1a) to give the diene 11 with an exo,exo-2,3-disubstituted norbornane skeleton.