Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents

Phosphorus–fluorine bonds have become increasingly relevant in the pharmaceutical industry. To continue their exploration, more efficient synthetic methods are needed. Here, we report the application of sulfone iminium fluoride (SIF) reagents to the synthesis of P­(V)–F bonds. The SIF reagents promo...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 11; pp. 1834 - 1838
Main Authors Miller, Lucy P., Vogel, James A., Harel, Shiraz, Krussman, Jenna M., Melvin, Patrick R.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.03.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
ONE-POT SYNTHESIS
DEOXYFLUORINATION
SARIN
FLUORINATION
KF
PHOSPHINE OXIDES
PROBE
EFFICIENT REAGENT
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Summary:Phosphorus–fluorine bonds have become increasingly relevant in the pharmaceutical industry. To continue their exploration, more efficient synthetic methods are needed. Here, we report the application of sulfone iminium fluoride (SIF) reagents to the synthesis of P­(V)–F bonds. The SIF reagents promote the deoxyfluorination of phosphinic acids in just 60 s with excellent yields and scope. The same P­(V)–F products can also be synthesized from secondary phosphine oxides using an SIF reagent.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c00274