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Issue 20, 2018
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Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives

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Abstract

A neutral cobalt(II) compound Cp*Co(1,2-Ph2PC6H4S) (1, Cp* = Me5C5) catalyzes the radical cyclization of 2-isocyano-biphenyls with alkyl halides, providing a variety of 6-substituted phenanthridines and phenanthridine-fused polycyclic compounds in good to excellent yields. The mild reaction conditions allow the catalysis to tolerate various alkyl halides for scaled-up syntheses. Polycyclic compounds with a 6-ethylpropanoate group at the C6 position can be hydrolyzed to provide the 6-ethyl substituted N-heterocycles, which exhibit useful emission properties upon protonation.

Graphical abstract: Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives

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Publication details

The article was received on 17 Aug 2018, accepted on 15 Sep 2018 and first published on 17 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00887F
Citation: Org. Chem. Front., 2018,5, 2997-3002
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    Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives

    X. Liu, C. Wu, J. Zhang, Y. Shi, S. Zhang, Y. Geng, C. Tung and W. Wang, Org. Chem. Front., 2018, 5, 2997
    DOI: 10.1039/C8QO00887F

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