Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones

J Org Chem. 2002 Jan 11;67(1):95-8. doi: 10.1021/jo010832v.

Abstract

A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Copper
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Iodides
  • Isomerism
  • Ketones / chemistry

Substances

  • Alkynes
  • Furans
  • Iodides
  • Ketones
  • Copper
  • cuprous iodide