Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles

A method for the radical functionalization of 1,2,4‐oxadiazoles using alkyl halides as precursors of radicals is described. The reaction efficiency is determined by potassium tetrafluoropyridinyl thiolate additive, which plays dual role. First, the thiolate converts alkyl halides into more reactive...

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Veröffentlicht in:Advanced synthesis & catalysis 2024-08, Vol.366 (16), p.3505-3510
Hauptverfasser: Frumkin, Alexander E., Levin, Vitalij V., Dilman, Alexander D.
Format: Artikel
Sprache:eng
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Zusammenfassung:A method for the radical functionalization of 1,2,4‐oxadiazoles using alkyl halides as precursors of radicals is described. The reaction efficiency is determined by potassium tetrafluoropyridinyl thiolate additive, which plays dual role. First, the thiolate converts alkyl halides into more reactive fluorinated aryl sulfides, which undergo photoredox activation of the C−S bond. Second, the thiolate decreases the unproductive loss of alkyl radicals by converting them back to the sulfides.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400075