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A convergent triflate displacement approach to (alpha-monofluoroalkyl)phosphonates.

[reaction: see text] Treatment of primary alkyl triflates or iodides with the potassium salt of diethyl (alpha-fluoro-alpha-phenylsulfonylmethyl)phosphonate yields (alpha-fluoro-alpha-phenylsulfonylalkyl)phosphonates. These can be cleanly desulfonated, in a matter of minutes, with Na(Hg) in MeOH/THF/NaH(2)PO(4). This two-step procedure complements previously reported triflate displacement approaches to alpha-nonfluorinated and alpha,alpha-difluorinated phosphonates.[1]

References

  1. A convergent triflate displacement approach to (alpha-monofluoroalkyl)phosphonates. Berkowitz, D.B., Bose, M., Asher, N.G. Org. Lett. (2001) [Pubmed]
 
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