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Palladium‐Catalysed Multiple Coupling Reactions of β‐Bromostyrene with Norbornene and Dicyclopentadiene
Author(s) -
Albrecht Karsten,
Meijere Armin De
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941271229
Subject(s) - dicyclopentadiene , norbornene , norbornane , chemistry , diene , palladium , yield (engineering) , coupling reaction , polymer chemistry , medicinal chemistry , organic chemistry , catalysis , polymerization , polymer , metallurgy , natural rubber , materials science
( E )‐β‐Bromostyrene [( E )‐ 2 ] reacts with norbornene ( 1a ) or dicyclopentadiene ( 1b ) in the presence of Pd(OAc) 2 , K 2 CO 3 , and n Bu 4 NBr 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.