Solvent controlled mechanistic dichotomy in a Au(III)-catalyzed, heterocyclization triggered, Nazarov reaction

Chem Commun (Camb). 2011 Jun 21;47(23):6707-9. doi: 10.1039/c1cc10920k. Epub 2011 May 10.

Abstract

Tandem Au(III)-catalyzed heterocyclization/Nazarov cyclizations leading to substituted carbocycle fused furans are described. An interesting dichotomy of reaction pathways as a function of solvent, confirmed by the isolation and trapping of reaction intermediates, provided a basis for computational studies that supported the experimental findings.

MeSH terms

  • Catalysis
  • Cyclization
  • Furans / chemistry
  • Gold / chemistry*
  • Solvents / chemistry*

Substances

  • Furans
  • Solvents
  • Gold