Selective aldol condensation or cyclotrimerization reactions catalyzed by FeCl3

Renzo Arias-Ugarte, Francis S. Wekesa, Michael Findlater

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

The inexpensive and commercially available FeCl3 catalyzes the selective homo-aldol condensation of aldehydes into the corresponding α-β unsaturated aldehydes, presumably through an unobserved aldol intermediate. Surprisingly the reaction course can be diverted to produce 1,3,5-trioxanes via aldehyde cyclotrimerization. Selectivity for trioxanes is achieved at lower temperatures and is enhanced by the presence of water, contrary to prior reports. A broad range of aliphatic and aromatic aldehydes are capable of undergoing these transformations; short reaction times, high yields, scalability, and easy purification processes are also described.

Original languageEnglish
Pages (from-to)2406-2411
Number of pages6
JournalTetrahedron Letters
Volume56
Issue number19
DOIs
StatePublished - May 6 2015

Keywords

  • Aldehydes
  • Aldol reactions
  • Catalysis
  • Cyclotrimerization
  • Lewis acid

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