N-Alkyl-4-boronopyridinium Halides versus Boric Acid as Catalysts for the Esterification of α-Hydroxycarboxylic Acids

N-Alkyl-4-boronopyridinium Halides versus Boric Acid as Catalysts for the Esterification of α-Hydroxycarboxylic Acids

Boric acid is a highly effective catalyst for the dehydrative esterification reaction between equimolar mixtures of α-hydroxycarboxylic acids and alcohols. In contrast, N-methyl-4-boronopyridinium iodide (2a) is a more effective catalyst than boric acid for the similar esterification in excess alcoh...

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Veröffentlicht in:Organic letters 2005-10, Vol.7 (22), p.5047-5050
Hauptverfasser: Maki, Toshikatsu, Ishihara, Kazuaki, Yamamoto, Hisashi
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creator Maki, Toshikatsu
Ishihara, Kazuaki
Yamamoto, Hisashi
description Boric acid is a highly effective catalyst for the dehydrative esterification reaction between equimolar mixtures of α-hydroxycarboxylic acids and alcohols. In contrast, N-methyl-4-boronopyridinium iodide (2a) is a more effective catalyst than boric acid for the similar esterification in excess alcohol. A heterogeneous catalyst, such as N-polystyrene-bound 4-boronopyridinium chloride, is also an effective catalyst and can be recovered by filtration.
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title N-Alkyl-4-boronopyridinium Halides versus Boric Acid as Catalysts for the Esterification of α-Hydroxycarboxylic Acids
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