Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate

Chem Commun (Camb). 2013 May 14;49(39):4376-8. doi: 10.1039/c2cc34609e. Epub 2012 Aug 3.

Abstract

Regioselective ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes was developed. The reaction involves a copper-catalyzed cycloaddition of an alkyne with an arylsulfonyl azide and a silver-catalyzed carbene formation followed by ring expansion of a cyclopropyl carbene intermediate.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry
  • Catalysis
  • Copper / chemistry
  • Cycloaddition Reaction
  • Cyclopropanes / chemistry*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Silver / chemistry
  • Triazoles / chemistry*

Substances

  • Alkynes
  • Azides
  • Cyclopropanes
  • Triazoles
  • carbene
  • Silver
  • Copper
  • Methane