Deoxyfluorination of Electron-Deficient Phenols

[Image: see text] In this study, we report a facile synthesis of 2-chloro-1,3-bis(2,6-diisopropylphenyl)imidazolium salts in aqueous media under ambient conditions using hypochlorite as a chlorinating agent. In addition, an air-stable and moisture-insensitive deoxyfluorination reagent based on poly[...

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Detalles Bibliográficos
Autores principales: Jelen, Jan, Tavčar, Gašper
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10226106/
https://www.ncbi.nlm.nih.gov/pubmed/37191994
http://dx.doi.org/10.1021/acs.orglett.3c01018
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author Jelen, Jan
Tavčar, Gašper
author_facet Jelen, Jan
Tavčar, Gašper
author_sort Jelen, Jan
collection PubMed
description [Image: see text] In this study, we report a facile synthesis of 2-chloro-1,3-bis(2,6-diisopropylphenyl)imidazolium salts in aqueous media under ambient conditions using hypochlorite as a chlorinating agent. In addition, an air-stable and moisture-insensitive deoxyfluorination reagent based on poly[hydrogen fluoride] salt is presented, which is capable of converting electron-deficient phenols or aryl silyl ethers into the corresponding aryl fluorides in the presence of DBU as a base, with good to excellent yields and high tolerance to functional groups.
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spelling pubmed-102261062023-05-30 Deoxyfluorination of Electron-Deficient Phenols Jelen, Jan Tavčar, Gašper Org Lett [Image: see text] In this study, we report a facile synthesis of 2-chloro-1,3-bis(2,6-diisopropylphenyl)imidazolium salts in aqueous media under ambient conditions using hypochlorite as a chlorinating agent. In addition, an air-stable and moisture-insensitive deoxyfluorination reagent based on poly[hydrogen fluoride] salt is presented, which is capable of converting electron-deficient phenols or aryl silyl ethers into the corresponding aryl fluorides in the presence of DBU as a base, with good to excellent yields and high tolerance to functional groups. American Chemical Society 2023-05-16 /pmc/articles/PMC10226106/ /pubmed/37191994 http://dx.doi.org/10.1021/acs.orglett.3c01018 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 Jelen, Jan
Tavčar, Gašper
Deoxyfluorination of Electron-Deficient Phenols
title Deoxyfluorination of Electron-Deficient Phenols
title_full Deoxyfluorination of Electron-Deficient Phenols
title_fullStr Deoxyfluorination of Electron-Deficient Phenols
title_full_unstemmed Deoxyfluorination of Electron-Deficient Phenols
title_short Deoxyfluorination of Electron-Deficient Phenols
title_sort deoxyfluorination of electron-deficient phenols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10226106/
https://www.ncbi.nlm.nih.gov/pubmed/37191994
http://dx.doi.org/10.1021/acs.orglett.3c01018
work_keys_str_mv AT jelenjan deoxyfluorinationofelectrondeficientphenols
AT tavcargasper deoxyfluorinationofelectrondeficientphenols

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