Three-component synthesis of beta-ketosulfonamides via visible-light mediated generation of sulfamoyl radicals

17 November 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we report photoredox-catalyzed, visible-light mediated 3-component synthesis of beta-ketosulfonamides from silyl enol ethers, N-aminopyridinium salts and the sulfur dioxide (SO2) surrogate DABSO (1,4-diazabicyclo[2.2.2]octane·bis (sulfur dioxide) adduct). This reaction is based on the photochemical generation of sulfamoyl radicals from N-aminopyridinium salts as nitrogen radical precursors and DABSO as easy-to-handle SO2 source. Trapping of the in situ generated sulfamoyl radicals with silyl enol ethers affords beta-ketosulfonamides in 63-97% yield in the presence of Eosin Y as organic photoredox catalyst.

Keywords

sulfonamide
sulfur dioxide
multicomponent reaction
photoredox-catalysis
sulfamoyl radical

Supplementary materials

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Description
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Supporting Information File 1
Description
Experimental details, spectral data, and copies of NMR spectra for all compounds prepared in this study
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