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The First Fluoride‐Free Hiyama Reaction of Vinylsiloxanes Promoted by Sodium Hydroxide in Water
Author(s) -
Alacid Emilio,
Nájera Carmen
Publication year - 2006
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.200600262
Subject(s) - chemistry , aryl , palladium , catalysis , polymer chemistry , fluoride , sodium hydroxide , hydroxide , polymerization , bromide , aqueous solution , coupling reaction , organic chemistry , vinyl bromide , inorganic chemistry , polymer , alkyl
The first cross‐coupling reaction between vinylalkoxysilanes and aryl bromides or chlorides promoted by aqueous sodium hydroxide under fluoride‐free conditions to provide styrenes is reported. The reaction is catalyzed by palladium(II) acetate or a 4‐hydroxyacetophenone oxime‐derived palladacycle either under thermal or microwave heating at 120 °C with low catalyst loading (0.01–1 mol % of palladium) in the presence of tetra‐ n ‐butylammonium bromide (TBAB) as additive in air. In the case of styryltriethoxysilane, the coupling with aryl or vinyl bromides takes place stereospecifically to give the corresponding stilbenes or dienes, respectively. These mild and simple reaction conditions prevent undesirable polymerization of the products.