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Acceleration of the Baylis–Hillman Reaction in the Presence of Ionic Liquids
Author(s) -
Kim Eun Jin,
Ko Soo Y.,
Song Choong Eui
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390087
Subject(s) - ionic liquid , chemistry , medicinal chemistry , reaction rate , organic chemistry , catalysis
Abstract The Baylis–Hillman reaction is accelerated in the presence of ionic liquids. Of various 1‐butyl‐3‐methylimidazolium (bmim)‐based ionic liquids tested, [bmim][PF 6 ] has been found to result in the highest rate increase. In the company of Lewis acid and H‐bond‐donor additives, the reaction rates further improve, albeit only modestly. A preparatively useful Baylis–Hillman procedure prescribes the use of [bmim][PF 6 ] with La(OTf) 3 and 2,2′2″‐nitrilotris[ethanol], in which the net effect of the ionic liquid is to bring about a more than twofold rate increase over the otherwise same reaction in MeCN.