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

Gendron, Thibault; Sander, Kerstin; Cybulska, Klaudia; Benhamou, Laure; Sin, PakKwanBrian; Khan, Aqsa; Wood, Michael; Porter, MichaelJ.; Årstad, Erik

doi:10.1021/jacs.8b06730

Article (Scientific journals)

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

Gendron, Thibault; Sander, Kerstin; Cybulska, Klaudia et al.

2018 • In Journal of the American Chemical Society, 140 (35), p. 11125–11132

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/296443

DOI
10.1021/jacs.8b06730

PubMed
30132661

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Keywords :

Chemistry; Radiolabeling; Precursors; Aromatic compounds; Cyclization; Nuclear Imaging

Abstract :

[en] 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 [18F]fluoride to give [18F]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency for clinically relevant PET tracers.

Research Center/Unit :

Institute of Nuclear Medicine, University College London
Department of Chemistry, University College London

Disciplines :

Chemistry
Radiology, nuclear medicine & imaging

Author, co-author :

Gendron, Thibault ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique-nucléaire

Sander, Kerstin

Cybulska, Klaudia

Benhamou, Laure

Sin, PakKwanBrian

Khan, Aqsa

Wood, Michael

Porter, MichaelJ.

Årstad, Erik

Language :

English

Title :

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

Publication date :

August 2018

Journal title :

Journal of the American Chemical Society

ISSN :

0002-7863

eISSN :

1520-5126

Publisher :

American Chemical Society (ACS)

Volume :

140

Issue :

Pages :

11125–11132

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://doi.org/10.1021%2Fjacs.8b06730

European Projects :

FP7 - 602102 - EPITARGET - Targets and biomarkers for antiepileptogenesis

Name of the research project :

EPITARGET - Targets and biomarkers for antiepileptogenesis

Funders :

EU - European Union
Leonard Wolfson Experimental Neurology Centre, Mallinckrodt
UCL Business
Wellcome Trust
CRUK - Cancer Research UK
EPSRC - Engineering and Physical Sciences Research Council

Funding number :

602102; C1519/A16463; 102407/Z/13/Z

Available on ORBi :

since 13 November 2022

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