A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates

David B Berkowitz, Mohua Bose, Nathan G. Asher

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

(Formula Presented) Treatment of primary alkyl triflates or iodides with the potassium salt of diethyl (α-fluoro-α-phenylsulfonylmethyl)phosphonate yields (α-fluoro-α-phenylsulfonylalkyl)phosphonates. These can be cleanly desulfonated, in a matter of minutes, with Na(Hg) in MeOH/THF/NaH2PO4. This two-step procedure complements previously reported triflate displacement approaches to α-nonfluorinated and α,α-difluorinated phosphonates.

Original languageEnglish (US)
Pages (from-to)2009-2012
Number of pages4
JournalOrganic Letters
Volume3
Issue number13
DOIs
StatePublished - Jun 28 2001

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Organophosphonates
complement
iodides
potassium
salts
Potassium Iodide
Iodides
Potassium
Salts

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates. / Berkowitz, David B; Bose, Mohua; Asher, Nathan G.

In: Organic Letters, Vol. 3, No. 13, 28.06.2001, p. 2009-2012.

Research output: Contribution to journalArticle

Berkowitz, David B ; Bose, Mohua ; Asher, Nathan G. / A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates. In: Organic Letters. 2001 ; Vol. 3, No. 13. pp. 2009-2012.
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