Organic Letters 2008-06-05

Zwitterionic salts as mild organocatalysts for transesterification.

Kazuaki Ishihara, Masatoshi Niwa, Yuji Kosugi

Index: Org. Lett. 10(11) , 2187-90, (2008)

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Abstract

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.