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

Alexey L. Trifonov, Liubov I. Panferova, Vitalij V. Levin, Vladimir A. Kokorekin and Alexander D. Dilman*

*N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Email:

A. L. Trifonov, L. I. Panferova, V. V. Levin, V. A. Kokorekin, A. D. Dilman, Org. Lett., 2020, 22, 2409-2413.

DOI: 10.1021/acs.orglett.0c00604

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Peri-xanthenoxanthene mediates a reaction of an iododifluoromethylphosphonium salt with unactivated alkenes under blue-light irradiation. This iododifluoromethylation proceeds via activation of the carbon-iodine bond to generate a (phosphonio)difluoromethyl radical cation, which attacks the double bond with subsequent quenching by the iodine.

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Key Words

iodination, difluoroalkanes, photochemistry, organocatalysis

ID: J54-Y2020