Visible-Light-Promoted Iododifluoromethylation of Alkenes via (Phosphonio)difluoromethyl Radical Cation

A reaction of an iododifluoromethylphosphonium salt with unactivated alkenes mediated by peri-xanthenoxanthene under blue-light irradiation is described. The reaction proceeds via activation of the carbon–iodine bond to generate (phosphonio)­difluoromethyl radical cation, which attacks the double bo...

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Veröffentlicht in:Organic letters 2020-03, Vol.22 (6), p.2409-2413
Hauptverfasser: Trifonov, Alexey L, Panferova, Liubov I, Levin, Vitalij V, Kokorekin, Vladimir A, Dilman, Alexander D
Format: Artikel
Sprache:eng
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Zusammenfassung:A reaction of an iododifluoromethylphosphonium salt with unactivated alkenes mediated by peri-xanthenoxanthene under blue-light irradiation is described. The reaction proceeds via activation of the carbon–iodine bond to generate (phosphonio)­difluoromethyl radical cation, which attacks the double bond with subsequent quenching by the iodine. The intermediate phosphonium salts are easily hydrolyzed, furnishing products of iododifluoromethylation of alkenes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00604