Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions

Akira Sakakura, Kimio Kawajiri, Takuro Ohkubo, Yuji Kosugi, Kazuaki Ishihara

Research output: Contribution to journalArticle

163 Citations (Scopus)

Abstract

With regard to atom economy and E-factor, catalytic condensation of carboxylic acids with equimolar amounts of alcohols is the most desirable. Although several highly active dehydration catalysts have been reported, more efficient alternatives are still strongly needed because the dehydrative esterification of tertiary alcohols, phenols, acid-sensitive alcohols, amino acids, and hardly soluble alcohols has never proceeded satisfactorily. Here we report new insights into the classical DMAP-catalyzed acylation of alcohols: surprisingly, only a 0.05-2 mol % of DMAP can efficiently promote acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to give the corresponding esters in high yields. Furthermore, we achieved the recovery and reuse of commercially available polystyrene-supported DMAP without using any solvents. These serendipitous findings provide widely useful and environmentally benign esterification methods, which might be more practical and reliable than catalytic dehydrative condensation methods, in particular, for the less reactive alcohols which hardly condense with carboxylic acid directly.

Original languageEnglish
Pages (from-to)14775-14779
Number of pages5
JournalJournal of the American Chemical Society
Volume129
Issue number47
DOIs
Publication statusPublished - Nov 28 2007
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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