Bulky diarylammonium arenesulfonates as mild and extremely active dehydrative ester condensation catalysts

Akira Sakakura, Shoko Nakagawa, Kazuaki Ishihara

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

More environmentally benign alternatives to current chemical processes, especially large-scale, fundamental reactions like 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 a loss of activity.

Original languageEnglish
Pages (from-to)422-433
Number of pages12
JournalTetrahedron
Volume62
Issue number2-3
DOIs
Publication statusPublished - Jan 9 2006
Externally publishedYes

Keywords

  • Ammonium sulfonates
  • Dehydration
  • Ester condensation
  • Hydrophobic effect
  • Steric effect

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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