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Forcing a cis ‐Product by Matrix Imprinting: Heck Reaction Catalyzed by Palladium Acetate Entrapped within cis ‐Imprinted Sol‐Gel Derived Silicates
Author(s) -
Tsvelikhovsky Dmitry,
Pessing Dikla,
Avnir David,
Blum Jochanan
Publication year - 2008
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.200800590
Subject(s) - chemistry , palladium , heck reaction , catalysis , aryl , silica gel , imprinting (psychology) , heterogeneous catalysis , organic chemistry , matrix (chemical analysis) , medicinal chemistry , polymer chemistry , combinatorial chemistry , chromatography , biochemistry , gene , alkyl
Abstract While the Heck coupling of aryl bromides with styrenes by palladium acetate entrapped within octylated silica sol‐gel forms almost entirely trans ‐stilbenes, the catalysis by the palladium compound within the cis ‐pre‐imprinted support gives stilbenes that are substantially enriched by cis ‐oriented isomers. Although the ceramic support is completely freed from the imprint prior to the coupling process, cis ‐stilbenes are formed with similar selectivities upon recycling of the catalyst systems for at least four consecutive runs.