Cx. Zhi et Qy. Chen, NOVEL AND PRACTICAL PREPARATION OF ALPHA-FLUORO-FUNCTIONALIZED ESTERSFROM FLUOROIODOACETATES, Journal of the Chemical Society. Perkin transactions. I, (14), 1996, pp. 1741-1747
The addition reaction of fluoroiodoacetates 2 to various electron-rich
alkenes 3 initiated by iron powder in dry THF at 70-80 degrees C gave
1 : 1 adducts 4 in good yields. A variety of functionalities in the a
lkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester coul
d be tolerated under the reaction conditions. Reduction of the adducts
4 with Zn-AcOH in ethanol or Zn-NiCl2 . 6H(2)O in moist THF was readi
ly accomplished, and the overall procedure was amenable to a convenien
t one-flask procedure, Treatment of fluoroiodoacetates 2 with electron
-deficient alkenes 7 in the presence of an Fe-CrCl3 . 6H(2)O-bpy bimet
al redox system in ethanol at 70-80 degrees C resulted in the formatio
n of iodine-free 1 : 1 adducts 8 in moderate to good yields. It is pro
posed that the addition reactions of fluoroiodoacetates 2 to electron-
rich and electron-deficient alkenes proceeded through a single-electro
n-transfer mechanism.