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The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [ c ]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[ c ]-, pyrrolo[2,3- c ]-, and indolo[2,3- c ]carbazoles were produced, respectively. The reaction proceeded through pyrrole and benzene ring construction accompanied by the formation of two carbon-carbon and one carbon-nitrogen bond and the cleavage of two aromatic C-H bonds. The mechanism of the reaction with pyrrole was investigated by density functional theory calculations. N , N '-dimethylated indolo[2,3- c ]carbazole showed dual ultraviolet-visible-near-infrared and fluorescence spectral changes upon electrolysis.

Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes