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

[Image: see text] 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 S...

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Autores principales: Miller, Lucy P., Vogel, James A., Harel, Shiraz, Krussman, Jenna M., Melvin, Patrick R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043933/
https://www.ncbi.nlm.nih.gov/pubmed/36897224
http://dx.doi.org/10.1021/acs.orglett.3c00274
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author Miller, Lucy P.
Vogel, James A.
Harel, Shiraz
Krussman, Jenna M.
Melvin, Patrick R.
author_facet Miller, Lucy P.
Vogel, James A.
Harel, Shiraz
Krussman, Jenna M.
Melvin, Patrick R.
author_sort Miller, Lucy P.
collection PubMed
description [Image: see text] 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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spelling pubmed-100439332023-03-29 Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents Miller, Lucy P. Vogel, James A. Harel, Shiraz Krussman, Jenna M. Melvin, Patrick R. Org Lett [Image: see text] 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. American Chemical Society 2023-03-10 /pmc/articles/PMC10043933/ /pubmed/36897224 http://dx.doi.org/10.1021/acs.orglett.3c00274 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Miller, Lucy P.
Vogel, James A.
Harel, Shiraz
Krussman, Jenna M.
Melvin, Patrick R.
Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents
title Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents
title_full Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents
title_fullStr Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents
title_full_unstemmed Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents
title_short Rapid Generation of P(V)–F Bonds Through the Use of Sulfone Iminium Fluoride Reagents
title_sort rapid generation of p(v)–f bonds through the use of sulfone iminium fluoride reagents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043933/
https://www.ncbi.nlm.nih.gov/pubmed/36897224
http://dx.doi.org/10.1021/acs.orglett.3c00274
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