Esterification Catalysis by Pyridinium p-Toluenesulfonate Revisited—Modification with a Lipid Chain for Improved Activities and Selectivities
Year: 2013
Type: article
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.]
Source: Synthetic Communications
Authors: Wei Wang, Huimin Liu, Shaoyi Xu, Yong Gao
Institutions: Wuhan University, Southern Illinois University Carbondale
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W2018187686