Treatment of perfluoroalkyl chlorides (R(F)Cl) with alkenes, alkynes, or aromatics in the presence of 0.1 equiv of nickel dichloride, 1.5 equiv of zinc powder, and 0.4 equiv of triphenylphosphine in DMF at 95-100 degrees C for 6-8 h give the corresponding perfluoroalkylated products in good yields. A single electron-transfer mechanism is suggested.

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Ethyl alpha-fluoro silyl enol ether is stereoselectively synthesized in high yield from inexpensive chlorofluoroacetate and Mg (or Zn) in DMF (or HMPA). Lewis acid promoted aldol reaction of this enol ether with aldehydes and ketones gives alpha-fluoro-beta-hydroxy esters in good to excellent yields.