Tandem cyclization of α-cyano α-alkynyl aryl ketones induced by tert-butyl hydroperoxide and tetrabutylammonium iodide

Org Lett. 2012 Dec 7;14(23):6024-7. doi: 10.1021/ol3028972. Epub 2012 Nov 28.

Abstract

The radical cascade protocol of the α-cyano α-TMS/aryl-capped alkynyl aryl ketones promoted by tert-butyl hydroperoxide under catalysis with tetrabutylammonium iodide in refluxing benzene has been developed, leading to the construction of a variety of highly functionalized [6,6,5] tricyclic frameworks in an efficient manner.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Hydrocarbons, Iodinated / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism
  • tert-Butylhydroperoxide / chemistry*

Substances

  • Alkynes
  • Hydrocarbons, Iodinated
  • Ketones
  • Quaternary Ammonium Compounds
  • tert-Butylhydroperoxide
  • tetrabutylammonium