Bulky Diarylammonium Arenesulfonates as Selective Esterification Catalysts

Kazuaki Ishihara,* Shoko Nakagawa, and Akira Sakakura
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan
J. Am. Chem. Soc., 2005, 127 (12), pp 4168–4169
DOI: 10.1021/ja050223v
Publication Date (Web): March 3, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ishihara@cc.nagoya-u.ac.jp

Abstract

Abstract Image

More environmentally benign alternatives to current chemical processes, especially large-scale, fundamental reactions such as ester condensations, are highly desirable for many reactions. Bulky diarylammonium pentafluorobenzenesulfonates and tosylates serve as extremely active dehydration catalysts for the ester condensation reaction of carboxylic acids with equimolar amounts of sterically demanding alcohols and acid-sensitive alcohols. Typically, the esterification reaction is performed in heptane by heating at 80 °C in the presence of 1 mol % of the catalyst without removing water. Esterification with primary alcohols proceeds without solvents even at room temperature. Furthermore, 4-(N-mesitylamino)polystyrene resin-bound pentafluorobenzenesulfonate can be recycled more than 10 times without activity loss.

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History

  • Published In Issue March 30, 2005
  • Received January 13, 2005

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