7766-74-7Relevant academic research and scientific papers
Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates
Zhi, Chengxin,Chen, Qing-Yun
, p. 1741 - 1747 (2007/10/03)
The addition reaction of fluoroiodoacetates 2 to various electron-rich alkenes 3 initiated by iron powder in dry THF at 70-80°C gave 1:1 adducts 4 in good yields. A variety of functionalities in the alkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester could be tolerated under the reaction conditions. Reduction of the adducts 4 with Zn-AcOH in ethanol or Zn-NiCl2·OH2O in moist THF was readily accomplished, and the overall procedure was amenable to a convenient one-flask procedure. Treatment of fluoroiodoacetates 2 with electron-deficient alkenes 7 in the presence of an Fe-CrCl3·OH2O-bpy bimetal redox system in ethanol at 70-80°C resulted in the formation of iodine-free 1:1 adducts 8 in moderate to good yields. It is proposed that the addition reactions of fluoroiodoacetates 2 to electronrich and electron-deficient alkenes proceeded through a single-electron-transfer mechanism.
