Issue 79, 2023

Selective access to dihydrophenanthridines and phenanthridinones via cyclisation of aryl amines onto N-tethered arynes

Abstract

5,6-Dihydrophenanthridines are prepared from aryl amines via intramolecular addition to N-tethered arynes under mild conditions. A new o-silylaryl triflate precursor was developed to increase reactivity and enable electron-rich and electron-poor aryl amines to undergo cyclisation. A complete switch in product selectivity occurs when the reaction is conducted in air, affording the corresponding phenanthridin-6(5H)-one as the sole product under otherwise identical reaction conditions.

Graphical abstract: Selective access to dihydrophenanthridines and phenanthridinones via cyclisation of aryl amines onto N-tethered arynes

Supplementary files

Article information

Article type
Communication
Submitted
23 Jun 2023
Accepted
11 Sep 2023
First published
12 Sep 2023
This article is Open Access
Creative Commons BY license

Chem. Commun., 2023,59, 11823-11826

Selective access to dihydrophenanthridines and phenanthridinones via cyclisation of aryl amines onto N-tethered arynes

W. Sun, M. Uttendorfer, F. I. M. Idiris, A. Y. R. Werling, K. Siddiq and C. R. Jones, Chem. Commun., 2023, 59, 11823 DOI: 10.1039/D3CC03027J

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