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.

中文翻译：

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通过金(i)催化叠氮二炔和芳烃级联反应直接合成芳基环化[c]咔唑†

金催化的带有叠氮基的共轭炔与芳烃的环化得到环化的[ c ]咔唑。使用苯、吡咯和吲哚衍生物作为亲核试剂，分别制备苯并[ c ]-、吡咯并[2,3- c ]-和吲哚[2,3- c ]咔唑。该反应通过吡咯和苯环的构建进行，并伴随着两​​个碳-碳键和一个碳-氮键的形成以及两个芳香族C-H键的断裂。通过密度泛函理论计算研究了与吡咯的反应机理。N , N'-二甲基化吲哚并[2,3- c ]咔唑在电解时表现出紫外-可见-近红外和荧光光谱的双重变化。