Diethylene Glycol Serving as Ethyne Equivalent: A Sustainable Approach toward 2,3-Disubstituted Furan

Org Lett. 2015 Aug 7;17(15):3643-5. doi: 10.1021/acs.orglett.5b01521. Epub 2015 Jul 13.

Abstract

In the presence of tert-butyl peroxide (TBHP), the copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol was developed leading to 2,3-disubstituted furan. Diethylene glycol serves as a cheap and environmentally friendly equivalent of ethyne, with the release of H2O and alcohol as clean wastes. The procedure involves a sequential O- and C- functionalization of β-ketoester by diethylene glycol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry
  • Ethylene Glycols / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Peroxides / chemistry*

Substances

  • Ethylene Glycols
  • Furans
  • Peroxides
  • diethylene glycol
  • Copper
  • tert-butyl peroxide
  • Acetylene