Alkyne-enol ether cross-metathesis in the presence of CuSO(4): direct formation of 3-substituted crotonaldehydes in aqueous medium

J Org Chem. 2009 Apr 17;74(8):3172-4. doi: 10.1021/jo900205x.

Abstract

An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO(4) and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from terminal alkyl-alkynes. All of the reactions were carried out under microwave irradiation and were completed in a few minutes. Water was used as the cosolvent, making this approach safer, economic, and desiderable from an enviromental point of view.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Alkynes / chemistry
  • Copper Sulfate / chemistry*
  • Ethers / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Solutions
  • Stereoisomerism
  • Structure-Activity Relationship
  • Water

Substances

  • Aldehydes
  • Alkenes
  • Alkynes
  • Ethers
  • Solutions
  • Water
  • 2-butenal
  • Copper Sulfate