Zwitterionic Salts as Mild Organocatalysts for Transesterification

Zwitterionic Salts as Mild Organocatalysts for Transesterification

The exothermic reaction of 3,5-bis(trifluoromethyl)phenyl or 4-nitrophenyl isothiocyanate with 4-pyrrolidinopyridine (PPY) gave the corresponding arylaminothiocarbonylpyridinium salts in quantitative yields. These novel zwitterionic salts were effective as organocatalysts for the transesterification...

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Bibliographic Details
Published in:Organic letters Vol. 10; no. 11; pp. 2187 - 2190
Main Authors: Ishihara, Kazuaki, Niwa, Masatoshi, Kosugi, Yuji
Format: Journal Article
Language:English
Published: United States American Chemical Society 05-06-2008
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Summary:The exothermic reaction of 3,5-bis(trifluoromethyl)phenyl or 4-nitrophenyl isothiocyanate with 4-pyrrolidinopyridine (PPY) gave the corresponding arylaminothiocarbonylpyridinium salts in quantitative yields. These novel zwitterionic salts were effective as organocatalysts for the transesterification reaction of an equimolar mixture of methyl carboxylates and alcohols in hydrocarbons such as heptane and octane under azeotropic reflux conditions with the removal of methanol. In sharp contrast, PPY was inert as a catalyst under the same reaction conditions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol8005979