Late-Stage F-18/F-19 Isotopic Exchange for the Synthesis of F-18-Labeled Sulfamoyl Fluorides

Synthesis of sulfamoyl [F-18]fluorides has been a challenging topic owing to the inefficient nucleophilic radiofluorination of sulfamoyl derivatives. Herein, we report an F-18/F-19 isotopic exchange approach to synthesize various sulfamoyl [F-18]fluorides, otherwise inaccessible via direct synthesis...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 7; pp. 2766 - 2771
Main Authors Jeon, Min Ho, Kwon, Young-Do, Kim, Min Pyeong, Torres, Gianluca Bartolini, Seo, Jeong Kon, Son, Jeongmin, Ryu, Young Hoon, Hong, Sung You, Chun, Joong-Hyun
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 02.04.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
POSITRON-EMISSION-TOMOGRAPHY
SUFEX CLICK CHEMISTRY
RADIOSYNTHESIS
DRUG DISCOVERY
F-18
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Summary:Synthesis of sulfamoyl [F-18]fluorides has been a challenging topic owing to the inefficient nucleophilic radiofluorination of sulfamoyl derivatives. Herein, we report an F-18/F-19 isotopic exchange approach to synthesize various sulfamoyl [F-18]fluorides, otherwise inaccessible via direct synthesis from amines, with high radiochemical yields up to 97% (30 examples). This late-stage labeling protocol offers an efficient route to yield functionalized molecules by diversifying the chemical library possessing sulfamoyl functionalities through nucleophilic F-18 incorporation within nitrogen-containing sulfur(VI) frameworks.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00671