Nucleophilic introduction of fluorinated alkyl groups into aldehydes and ketones using the corresponding alkyl halide with samarium(II) iodide
1997; Issue: 5 Linguagem: Inglês
10.1039/a606048j
ISSN2050-8255
AutoresMasato Yoshida, Daiki Suzuki, Masahiko Iyoda,
Tópico(s)Fluorine in Organic Chemistry
ResumoFluorinated 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.
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