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Feeding the Heck Reaction with Alcohol: One‐Pot Synthesis of Stilbenes from Aryl Alcohols and Bromides
Author(s) -
Colbon Paul,
Barnard Jonathan H.,
Purdie Mark,
Mulholland Keith,
Kozhevnikov Ivan,
Xiao Jianliang
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200340
Subject(s) - chemistry , aryl , heck reaction , organic chemistry , alcohol , dehydration , solvent , palladium , catalysis , ethanol , alkyl , biochemistry
Aryl alcohols are employed as feedstock for the Heck reaction. Keggin‐type heteropolyacids catalyse the selective dehydration of the alcohols to styrenes, which, in one‐pot, undergo palladium‐catalysed Heck arylation with aryl bromides, affording broadly functionalised stilbenes. The choice of solvent is critical for the cascade dehydration–Heck reaction, with electron‐rich aryl alcohols preferring a basic medium while electron‐deficient ones demanding solvents of lower basicity.