Nucleophilic Difluoromethylation Using (Bromodifluoromethyl)trimethylsilane

Nucleophilic Difluoromethylation Using (Bromodifluoromethyl)trimethylsilane

A combination of (bromodifluoromethyl)trimethylsilane (Me3SiCF2Br), triphenylphosphine, and DMPU serves as a source of difluorinated phosphorus ylide Ph3P═CF2 under mild conditions. The system was used to effect nucleophilic difluoromethylation of ketones and nitro alkenes. The reaction efficiency i...

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Veröffentlicht in:Organic letters 2016-07, Vol.18 (14), p.3458-3461
Hauptverfasser: Trifonov, Alexey L, Zemtsov, Artem A, Levin, Vitalij V, Struchkova, Marina I, Dilman, Alexander D
Format: Artikel
Sprache:eng
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Zusammenfassung:A combination of (bromodifluoromethyl)trimethylsilane (Me3SiCF2Br), triphenylphosphine, and DMPU serves as a source of difluorinated phosphorus ylide Ph3P═CF2 under mild conditions. The system was used to effect nucleophilic difluoromethylation of ketones and nitro alkenes. The reaction efficiency is believed to be associated with Lewis acidic activation of the substrates by a silylium species formed upon generation of the phosphorus ylide.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01641