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

Authors

Lucy P. Miller, Bryn Mawr College
James A. Vogel, Bryn Mawr College
Shiraz Harel, Bryn Mawr College
Jenna M. Krussman, Bryn Mawr College
Patrick R. Melvin, Bryn Mawr CollegeFollow

Document Type

Article

Version

Author's Final Manuscript

Publication Title

Organic Letters

Volume

25

Publication Date

2023

Abstract

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.

Citation

Miller, L. P., Vogel, J. A., Harel, S., Krussman, J. M., and P. R. Melvin. 2023. "Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents." Org. Lett. 25.11: 1834–1838.

DOI

https://doi.org/10.1021/acs.orglett.3c00274