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

Thibault Gendron | Zendy; Kerstin Sander | Zendy; Klaudia Cybulska | Zendy; Laure Benhamou | Zendy; Pak Kwan Brian Sin | Zendy; Aqsa Khan | Zendy; Michael L. Wood | Zendy; Michael J. Porter | Zendy; Erik Årstad | Zendy

Open Access

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

Author(s) -

Thibault Gendron,

Kerstin Sander,

Klaudia Cybulska,

Laure Benhamou,

Pak Kwan Brian Sin,

Aqsa Khan,

Michael L. Wood,

Michael J. Porter,

Erik Årstad

Publication year - 2018

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.8b06730

Subject(s) - chemistry , sulfonium , dibenzothiophene , intramolecular force , ring (chemistry) , fluoride , organic chemistry , combinatorial chemistry , sulfur , salt (chemistry) , inorganic chemistry

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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