Abstract (E)‐β‐Bromostyrene [(E)‐2] reacts with norbornene (1a) or dicyclopentadiene (1b) in the presence of Pd(OAc)2, K2CO3, and nBu4NBr in DMF to yield a mixture of the 2:1 coupling products 4 and 5, while (Z)‐β‐bromostyrene [(Z)‐2] gives exclusively 5. Under analogous conditions, (Z)‐3‐iodoacrylic acid (6) reacts with norbornene (1a) to give the diene 11 with an exo, exo‐2,3‐disubstituted norbornane skeleton.
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Albrecht et al. (1994) studied this question.
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