Abstract
We report the synthesis of 1,4-diaryl-5-cyano-1,2,3-triazoles from azides and alkynes via two copper-mediated steps. Aryl-substituted cyanotriazoles are emissive in nonpolar solvents. When the N1-aryl group is electron-donating, the photoconversion of a cyanotriazole to a cyanoindole is efficient. Each of the seven pairs of 4- and 5-cyanotriazole isomers is photoconverted to either distinctive cyanoindoles without rearrangement or a major cyanoindole product via the presumed common intermediate azirine. The resulting cyanoindoles appear to be stronger emitters in polar solvents than the parent cyanotriazoles.
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