Wei Wang, Huimin Liu, Shaoyi Xu
May 31, 2013
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0
Influential Citations
5
Citations
Journal
Synthetic Communications
Abstract
Abstract The lipid analogs of pyridinium p-toluenesulfonate (PPTS) were examined for catalysis of the condensation of an equimolar mixture of carboxylic acids and alcohols under mild conditions without removal of water. Although PPTS is a poor catalyst, the introduction of a lipid chain and nitro group significantly improved the activity of PPTS and led to selectivity at suppressing the elimination side reactions of alcohols. 2-Oleamido-5-nitro-pyridinium p-toluenesulfonate (6) is a lead catalyst that promoted various esterification reactions with yields up to 99%. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.] GRAPHICAL ABSTRACT