Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 2, Pages 720-725Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b13071
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Funding
- European Union [721902]
- Dutch Science Foundation (NWO) (VIDI, SensPhotoFlow) [14150]
- Marie Curie Actions (MSCA) [721902] Funding Source: Marie Curie Actions (MSCA)
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Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.
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