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.
Berkowitz
D B
DB
Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588-0304, USA. dbb@unlserve.unl.edu
Bose
M
M
Asher
N G
NG