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

Fluorinated alkyl groups such as PhCF(2), C6F13, CF3CCl2 and CF(2)CO(2)Et 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 PhCF(2)SiMe(3), C(6)F(13)SiMe(3) and C(6)F(13)SiMe(2)Pr(i) 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 (PrOH)-O-i.