The introduction of P–F bonds using aqueous fluoride ion and a water soluble carbodiimide: a convenient alternative synthesis of phosphorofluoridates and phosphonofluoridates

[Display omitted] •Ease of synthesis of P–F bonds from phosphates.•Ease of synthesis of P–F bonds from phosphonates.•Detailed NMR studies of the products containing P, F, and a chiral center in one case.•Reaction mechanism and kinetic analysis. The chemistry of ribonucleotides and other phosphates i...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 56; no. 38; pp. 5272 - 5274
Main Authors:	Aldersley, Michael F., Joshi, Prakash C., Ott, Elizabeth L., McCallum, Scott A., Kirby, Anthony J.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 16-09-2015
Subjects:	Carbodiimide NMR studies Phosphonofluoridate Phosphorofluoridate Potassium fluoride Phosphonofluoridate Potassium fluoride Carbodiimide Phosphorofluoridate NMR studies
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Summary:	[Display omitted] •Ease of synthesis of P–F bonds from phosphates.•Ease of synthesis of P–F bonds from phosphonates.•Detailed NMR studies of the products containing P, F, and a chiral center in one case.•Reaction mechanism and kinetic analysis. The chemistry of ribonucleotides and other phosphates is extended to include their reactions with potassium fluoride in aqueous solution in the presence of a water soluble carbodiimide. High yields (>98%) of phosphorofluoridates are formed. A combination of HPLC, mass spectrometry, and NMR confirms the identities of the products. The methodology is applied, with equally satisfactory outcomes, to the physiologically active phosphonates Adefovir® and Tenofovir®, providing new compounds. Detailed NMR studies of the new phosphonofluoridates are reported.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2015.07.036