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Issue 44, 2018
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Direct synthesis of aryl-annulated [c]carbazoles by gold(I)-catalysed cascade reaction of azide-diynes and arenes

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Abstract

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.

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

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Publication details

The article was received on 08 Aug 2018, accepted on 08 Sep 2018 and first published on 10 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03525C
Citation: Chem. Sci., 2018,9, 8416-8425
  • Open access: Creative Commons BY license
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    Direct synthesis of aryl-annulated [c]carbazoles by gold(I)-catalysed cascade reaction of azide-diynes and arenes

    Y. Kawada, S. Ohmura, M. Kobayashi, W. Nojo, M. Kondo, Y. Matsuda, J. Matsuoka, S. Inuki, S. Oishi, C. Wang, T. Saito, M. Uchiyama, T. Suzuki and H. Ohno, Chem. Sci., 2018, 9, 8416
    DOI: 10.1039/C8SC03525C

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