A novel and highly efficient synthesis of gem-difluorocyclopropanes

…, V Kruger, O Bautista, JX Duan, AR Li, WR Dolbier…

Index: Tian, Feng; Kruger, Virginie; Bautista, Olivia; Duan, Jian-Xin; Li, An-Rong; Dolbier Jr., William R.; Chen, Qing-Yun Organic Letters, 2000 , vol. 2, # 4 p. 563 - 564

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Citation Number: 61

Abstract

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.