Aconvenientanddirectper(poly)fluoroalkylmethyl-mtroducingcyclopropanationreactionwasdescribed.InthepresenceofCrCl3/Fe,per(poly)fluoroalkyliodidesreactedwithdiethylallylmalonateanditsanalogstogiveper(poly)fluoroalkylmethyl-substitutedelectrophiliccyclopropanederivativesinhighyields.Thisreactionwasconsideredtoproceedbytwosteps:radicaladditionfollowedbycyclopropanation.