Abstract
The palladium-catalyzed telomerization of 1,3-butadiene with alcohols has been studied in presence of palladium and imidazolium salts, which form in situ carbene ligands. Among the different imidazolium salts tested 1,3-dimesitylimidazolium chloride ( 7), 1,3-bis(ferrocenylmethyl)benzimidazolium tetraphenylborate ( 12) and 1,3-bis(2-ferrocenylethyl)benzimidazolium bromide ( 13) gave the best yields of the desired octadienyl ethers. Significantly improved regioselectivities for the linear octadienylethers are obtained in the reaction of 1,3-butadiene and methanol compared to the previously optimized palladium/triphenylphosphine catalyst. Using n-butanol and iso-propanol the palladium carbene catalysts lead to a considerable increase in the corresponding telomerization products compared to standard palladium/triphenylphosphine catalysts.
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