Issue 17, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
06 Jul 2018
Accepted
26 Jul 2018
First published
27 Jul 2018

Org. Chem. Front., 2018,5, 2555-2559

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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