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

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). © 2013 American Chemical Society.