Thermal vs. Visible-Light Photoredox-Catalyzed Cascade Radical Cyclization Involving SO2 Fixation to Access 6-Alkylsulfonylmethyl Phenanthridines

22 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Convenient access to 6-alkylsulfonylmethyl phenanthridines has been demonstrated both under thermal and visible-light photoredox-catalyzed conditions. A cascade of radical cyclization is triggered on exposure of biphenyl vinyl azides to the in-situ generated alkyl sulfonyl radicals from 4-substituted Hanztsch esters in the presence of an SO2 surrogate. Transition metal-free, mild reaction conditions, and broad substrate scope constitute some of the highlights of the approach. Also, the synthetic utility of the accessed 6-alkylsulfonylmethyl phenanthridines has been demonstrated.

Keywords

visible-light photoredox catalysis
SO2 fixation
Phenanthridines
Cascade radical cyclization

Supplementary materials

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Supporting Information
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The Supporting Information contains experimental details, detailed mechanistic probing studies information and characterization data of all compounds, copies of 1H, 13C, and 19F NMR spectra of all the synthesized compounds, and X-ray data for 3f (PDF).
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