Nucleophilic introduction of fluorinated alkyl groups into aldehydes and ketones using the corresponding alkyl halide with samarium(II) iodide

Abstract

Fluorinated alkyl groups such as PhCF₂, C₆F₁₃, CF₃CCl₂ and CF₂CO₂Et are nucleophilically introduced into an aldehyde or ketone using fluorinated alkyl halides with SmI₂; the reaction proceeds effectively at room temperature to give the corresponding alcohol. Furthermore, the synthesis of PhCF₂SiMe₃, C₆F₁₃SiMe₃ and C₆F₁₃SiMe₂Prⁱ is achieved by reaction of the halide with SmI₂ in the presence of the silyl chloride; the resultant fluoroalkylated silyl compounds are used as reagents for nucleophilic fluoroalkylation. 2-Chloro-3,3,3-trifluoropropene derivatives are also prepared selectively by the reaction of CF₃CCl₃ with an excess of SmI₂ in the presence of an aldehyde and PrⁱOH.