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Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)

Electrochemical fluorination of methyl(phenylthio)acetate was achieved using tetrabutylammonium fluoride (TBAF). Electrochemical fluorination was performed under potentiostatic anodic oxidation using an undivided cell in acetonitrile containing TBAF and triflic acid. The influence of several paramet...

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Autores principales: Balandeh, Mehrdad, Waldmann, Christopher, Shirazi, Daniela, Gomez, Adrian, Rios, Alejandra, Allison, Nathanael, Khan, Asad, Sadeghi, Saman
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5589193/
https://www.ncbi.nlm.nih.gov/pubmed/28890550
http://dx.doi.org/10.1149/2.0941709jes
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author Balandeh, Mehrdad
Waldmann, Christopher
Shirazi, Daniela
Gomez, Adrian
Rios, Alejandra
Allison, Nathanael
Khan, Asad
Sadeghi, Saman
author_facet Balandeh, Mehrdad
Waldmann, Christopher
Shirazi, Daniela
Gomez, Adrian
Rios, Alejandra
Allison, Nathanael
Khan, Asad
Sadeghi, Saman
author_sort Balandeh, Mehrdad
collection PubMed
description Electrochemical fluorination of methyl(phenylthio)acetate was achieved using tetrabutylammonium fluoride (TBAF). Electrochemical fluorination was performed under potentiostatic anodic oxidation using an undivided cell in acetonitrile containing TBAF and triflic acid. The influence of several parameters including: oxidation potential, time, temperature, sonication, TBAF concentration and triflic acid concentration on fluorination efficiency were studied. It was found that the triflic acid to TBAF concentration ratio plays a key role in the fluorination efficiency. Electrochemical fluorination resulted in formation of mono-fluorinated methyl 2-fluoro-2-(phenylthio)acetate verified by gas chromatography–mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) Spectroscopy. Under optimum conditions 44 ± 3% mono fluorination yield was obtained after a 30 min electrolysis. Electrochemical radiofluorination for the synthesis of methyl 2-[(18)F]fluoro-2-(phenothio) acetate was also achieved with the same optimized electrochemical cell parameters where TBAF was first passed through an anion exchange resin containing fluorine-18. A radiochemical fluorination efficiency of 7 ± 1% was achieved after 30 min of electrolysis.
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spelling pubmed-55891932017-09-07 Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF) Balandeh, Mehrdad Waldmann, Christopher Shirazi, Daniela Gomez, Adrian Rios, Alejandra Allison, Nathanael Khan, Asad Sadeghi, Saman J Electrochem Soc Article Electrochemical fluorination of methyl(phenylthio)acetate was achieved using tetrabutylammonium fluoride (TBAF). Electrochemical fluorination was performed under potentiostatic anodic oxidation using an undivided cell in acetonitrile containing TBAF and triflic acid. The influence of several parameters including: oxidation potential, time, temperature, sonication, TBAF concentration and triflic acid concentration on fluorination efficiency were studied. It was found that the triflic acid to TBAF concentration ratio plays a key role in the fluorination efficiency. Electrochemical fluorination resulted in formation of mono-fluorinated methyl 2-fluoro-2-(phenylthio)acetate verified by gas chromatography–mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) Spectroscopy. Under optimum conditions 44 ± 3% mono fluorination yield was obtained after a 30 min electrolysis. Electrochemical radiofluorination for the synthesis of methyl 2-[(18)F]fluoro-2-(phenothio) acetate was also achieved with the same optimized electrochemical cell parameters where TBAF was first passed through an anion exchange resin containing fluorine-18. A radiochemical fluorination efficiency of 7 ± 1% was achieved after 30 min of electrolysis. 2017-07-14 2017 /pmc/articles/PMC5589193/ /pubmed/28890550 http://dx.doi.org/10.1149/2.0941709jes Text en This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 License (CC BY, http://creativecommons.org/licenses/by/4.0/), which permits unrestricted reuse of the work in any medium, provided the original work is properly cited.
spellingShingle Article
Balandeh, Mehrdad
Waldmann, Christopher
Shirazi, Daniela
Gomez, Adrian
Rios, Alejandra
Allison, Nathanael
Khan, Asad
Sadeghi, Saman
Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)
title Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)
title_full Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)
title_fullStr Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)
title_full_unstemmed Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)
title_short Electrochemical Fluorination and Radiofluorination of Methyl(phenylthio)acetate Using Tetrabutylammonium Fluoride (TBAF)
title_sort electrochemical fluorination and radiofluorination of methyl(phenylthio)acetate using tetrabutylammonium fluoride (tbaf)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5589193/
https://www.ncbi.nlm.nih.gov/pubmed/28890550
http://dx.doi.org/10.1149/2.0941709jes
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