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

ABSTRACT: 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.

SUBMITTER: Gendron T

PROVIDER: S-EPMC6128620 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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

Gendron Thibault T Sander Kerstin K Cybulska Klaudia K Benhamou Laure L Sin Pak Kwan Brian PKB Khan Aqsa A Wood Michael M Porter Michael J MJ Årstad Erik E

Journal of the American Chemical Society 20180822 35

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. ...[more]

PMID: 30132661

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