A Novel and Highly Efficient Synthesis of gem-Difluorocyclopropanes

A Novel and Highly Efficient Synthesis of gem-Difluorocyclopropanes

A new and highly versatile source of difluorocarbene is reported. Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) undergoes decomposition in the presence of catalytic fluoride to form difluorocarbene under conditions that allow its addition to relatively electron deficient alkenes in high yield....

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Veröffentlicht in:Organic letters 2000-02, Vol.2 (4), p.563-564
Hauptverfasser: Tian, Feng, Kruger, Virginie, Bautista, Olivia, Duan, Jian-Xin, Li, An-Rong, Dolbier, William R, Chen, Qing-Yun
Format: Artikel
Sprache:eng
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Zusammenfassung:A new and highly versatile source of difluorocarbene is reported. Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) undergoes decomposition in the presence of catalytic fluoride to form difluorocarbene under conditions that allow its addition to relatively electron deficient alkenes in high yield. For example, unprecedented CF2:  addition to n-butyl acrylate proceeded in 73% yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0055622