Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 20, Pages 4900-4906Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200304895
Keywords
allylation; homogeneous catalysis; hydrogen bonds; ionic liquids; palladium
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Neutral allylic alkylation reactions, in which a base is generated in situ and which hence require no external bases, can significantly be retarded when carried out in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]). Evidence suggests that the base or base precursor enters into hydrogen bonding with the imidazolium cation and is thus made less readily available for deprotonation of pre-nucleophiles. However, the reaction proceeds well in the presence of stronger bases that are capable of deprotonation. Whilst the phenomenon of hydrogen bonding in ionic liquids can be detrimental to reactions such as allylic alkylation, it can be exploited to suppress unwanted allylic isomerization.
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