The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions

Cheng Ming Chu, Wan Ju Huang, Chaowei Lu, Pohsi Wu, Ju Tsung Liu, Ching Fa Yao

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

The 1,4-addition of various thiols to α,β-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with α,β-unsaturated ketones present in the reaction.

Original languageEnglish
Pages (from-to)7375-7380
Number of pages6
JournalTetrahedron Letters
Volume47
Issue number41
DOIs
Publication statusPublished - 2006 Oct 9

Keywords

  • 1,4-Addition
  • Anhydrous iron(III) chloride
  • Solvent free
  • α,β-Unsaturated ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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