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Issue 17, 2018
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Synthesis of 6-(sulfonylmethyl)phenanthridines through a reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, and vinyl azides

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Abstract

Synthesis of 6-(sulfonylmethyl)phenanthridines through a three-component reaction of aryldiazonium tetrafluoroborates, a sulfur dioxide surrogate of DABCO·(SO2)2, and vinyl azides under metal- and additive-free conditions is achieved. The arylsulfonyl radicals generated in situ would initiate the sulfonylation of vinyl azides. Subsequent intramolecular cyclization and deprotonation would provide 6-(sulfonylmethyl)phenanthridines in good yields. High efficiency under extremely mild conditions with the insertion of sulfur dioxide through a radical process is observed.

Graphical abstract: Synthesis of 6-(sulfonylmethyl)phenanthridines through a reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, and vinyl azides

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Publication details

The article was received on 06 Jul 2018, accepted on 26 Jul 2018 and first published on 27 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00679B
Citation: Org. Chem. Front., 2018,5, 2555-2559
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    Synthesis of 6-(sulfonylmethyl)phenanthridines through a reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, and vinyl azides

    X. Wang, Y. Li, G. Qiu and J. Wu, Org. Chem. Front., 2018, 5, 2555
    DOI: 10.1039/C8QO00679B

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