Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination

[Image: see text] Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [(18)F]fluoride to give [(18)F]fluoroarenes in...

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Autores principales: Gendron, Thibault, Sander, Kerstin, Cybulska, Klaudia, Benhamou, Laure, Sin, Pak Kwan Brian, Khan, Aqsa, Wood, Michael, Porter, Michael J., Årstad, Erik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6128620/
https://www.ncbi.nlm.nih.gov/pubmed/30132661
http://dx.doi.org/10.1021/jacs.8b06730
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author Gendron, Thibault
Sander, Kerstin
Cybulska, Klaudia
Benhamou, Laure
Sin, Pak Kwan Brian
Khan, Aqsa
Wood, Michael
Porter, Michael J.
Årstad, Erik
author_facet Gendron, Thibault
Sander, Kerstin
Cybulska, Klaudia
Benhamou, Laure
Sin, Pak Kwan Brian
Khan, Aqsa
Wood, Michael
Porter, Michael J.
Årstad, Erik
author_sort Gendron, Thibault
collection PubMed
description [Image: see text] Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [(18)F]fluoride to give [(18)F]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency for clinically relevant PET tracers.
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spelling pubmed-61286202018-09-10 Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination Gendron, Thibault Sander, Kerstin Cybulska, Klaudia Benhamou, Laure Sin, Pak Kwan Brian Khan, Aqsa Wood, Michael Porter, Michael J. Årstad, Erik J Am Chem Soc [Image: see text] Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [(18)F]fluoride to give [(18)F]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency for clinically relevant PET tracers. American Chemical Society 2018-08-22 2018-09-05 /pmc/articles/PMC6128620/ /pubmed/30132661 http://dx.doi.org/10.1021/jacs.8b06730 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Gendron, Thibault
Sander, Kerstin
Cybulska, Klaudia
Benhamou, Laure
Sin, Pak Kwan Brian
Khan, Aqsa
Wood, Michael
Porter, Michael J.
Årstad, Erik
Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination
title Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination
title_full Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination
title_fullStr Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination
title_full_unstemmed Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination
title_short Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic (18)F-Fluorination
title_sort ring-closing synthesis of dibenzothiophene sulfonium salts and their use as leaving groups for aromatic (18)f-fluorination
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6128620/
https://www.ncbi.nlm.nih.gov/pubmed/30132661
http://dx.doi.org/10.1021/jacs.8b06730
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