{"title":"Three-Component Synthesis of β-Ketosulfonamides via Visible-Light-Mediated Generation of Sulfamoyl Radicals","authors":"Kamil Hofman, Marius Friedrich, Georg Manolikakes","doi":"10.1002/cctc.202401899","DOIUrl":null,"url":null,"abstract":"<p>In this study, we report a photoredox-catalyzed, visible-light-mediated three-component synthesis of β-ketosulfonamides from silyl enol ethers, <i>N</i>-aminopyridinium salts, and the sulfur dioxide (SO<sub>2</sub>) 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 <i>N</i>-aminopyridinium salts as nitrogen radical precursors and DABSO as an easy-to-handle, solid SO<sub>2</sub> source. Trapping of the in situ-generated sulfamoyl radicals with silyl enol ethers affords pharmaceutically relevant β-ketosulfonamides in 63%–91% yields.</p>","PeriodicalId":141,"journal":{"name":"ChemCatChem","volume":"17 6","pages":""},"PeriodicalIF":3.9000,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cctc.202401899","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemCatChem","FirstCategoryId":"92","ListUrlMain":"https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.202401899","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
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 (SO2) 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 SO2 source. Trapping of the in situ-generated sulfamoyl radicals with silyl enol ethers affords pharmaceutically relevant β-ketosulfonamides in 63%–91% yields.
期刊介绍：
With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.
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