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Palladium‐Catalysed Multiple Coupling Reactions of β‐Bromostyrene with Norbornene and Dicyclopentadiene

K. Albrecht, Armin de Meijere

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Abstract

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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What this paper is about

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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Available abstract

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.

Key concepts: Dicyclopentadiene, Norbornene, Norbornane, Chemistry, Diene, Palladium, Yield (engineering), Coupling reaction

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Palladium‐Catalysed Multiple Coupling Reactions of β‐Bromostyrene with Norbornene and Dicyclopentadiene — Research Paper | ScholarLens