A click chemistry approach to 5,5'-disubstituted-3,3'-bisisoxazoles from dichloroglyoxime and alkynes: luminescent organometallic iridium and rhenium bisisoxazole complexes

J Org Chem. 2013 Jul 19;78(14):7298-304. doi: 10.1021/jo4008755. Epub 2013 Jul 2.

Abstract

5,5'-Disubstituted-3,3'-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5'-disubstituted 3,3'-bisisoxazole over the 4,5'-regioisomer. Organometallic iridium and rhenium bisisoxazole complexes are luminescent with emission wavelengths varying depending upon the identity of the 5,5'-substituent (phenyl, butyl).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Click Chemistry
  • Crystallography, X-Ray
  • Iridium / chemistry*
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry*
  • Luminescence*
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Oximes / chemistry*
  • Rhenium / chemistry*

Substances

  • Alkynes
  • Isoxazoles
  • Organometallic Compounds
  • Oximes
  • Iridium
  • Rhenium