Issue 44, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Aug 2018
Accepted
08 Sep 2018
First published
10 Sep 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 8416-8425

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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