Three‐Component Synthesis of β‐Ketosulfonamides via Visible‐Light‐Mediated Generation of Sulfamoyl Radicals

Abstract In this study, we report a photoredox‐catalyzed, visible‐light‐mediated three‐component synthesis of β‐ketosulfonamides from silyl enol ethers, N ‐aminopyridinium salts, and the sulfur dioxide (SO 2 ) surrogate DABSO (1,4‐diazabicyclo[2.2.2]octane·bis (sulfur dioxide) adduct). Eosin Y is used as readily available and cost‐efficient organic photoredox catalyst. This method is based on the photochemical generation of sulfamoyl radicals as key intermediates from N ‐aminopyridinium salts as nitrogen radical precursors and DABSO as an easy‐to‐handle, solid SO 2 source. Trapping of the in situ‐generated sulfamoyl radicals with silyl enol ethers affords pharmaceutically relevant β‐ketosulfonamides in 63%–91% yields.

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Journal
ChemCatChem
Published
2024-12-23
DOI
https://doi.org/10.1002/cctc.202401899
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.25
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article

Three‐Component Synthesis of β‐Ketosulfonamides via Visible‐Light‐Mediated Generation of Sulfamoyl Radicals

Marius Friedrich, Georg Manolikakes, Kamil Hofman
1 citations
ChemCatChem
Sulfur-Based Synthesis Techniques
0.25
article

Three‐Component Synthesis of β‐Ketosulfonamides via Visible‐Light‐Mediated Generation of Sulfamoyl Radicals

Marius Friedrich, Georg Manolikakes, Kamil Hofman
article en
1 citations

Abstract

Abstract In this study, we report a photoredox‐catalyzed, visible‐light‐mediated three‐component synthesis of β‐ketosulfonamides from silyl enol ethers, N ‐aminopyridinium salts, and the sulfur dioxide (SO 2 ) surrogate DABSO (1,4‐diazabicyclo[2.2.2]octane·bis (sulfur dioxide) adduct). Eosin Y is used as readily available and cost‐efficient organic photoredox catalyst. This method is based on the photochemical generation of sulfamoyl radicals as key intermediates from N ‐aminopyridinium salts as nitrogen radical precursors and DABSO as an easy‐to‐handle, solid SO 2 source. Trapping of the in situ‐generated sulfamoyl radicals with silyl enol ethers affords pharmaceutically relevant β‐ketosulfonamides in 63%–91% yields.

ChemCatChemVol. 17(6)
University of Kaiserslautern (DE), Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau (DE)
Clean water and sanitation
Openalex Percentile: Top 45%
Sulfur-Based Synthesis Techniques
0.25
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