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

Min Ho Jeon, Young‐Do Kwon, Min Pyeong Kim, Gianluca Bartolini Torres, Jeong Kon Seo, Jeongmin Son, Young Hoon Ryu, Sung You Hong, Joong‐Hyun Chun

2021Organic Letters27 citationsDOIOpen Access PDF

Abstract

Synthesis of sulfamoyl [18F]fluorides has been a challenging topic owing to the inefficient nucleophilic radiofluorination of sulfamoyl derivatives. Herein, we report an 18F/19F isotopic exchange approach to synthesize various sulfamoyl [18F]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 18F incorporation within nitrogen-containing sulfur(VI) frameworks.

Topics & Concepts

ChemistryNucleophileYield (engineering)SulfurMoleculeRadiochemistryMedicinal chemistryCombinatorial chemistryCatalysisOrganic chemistryMetallurgyMaterials scienceFluorine in Organic ChemistrySynthesis and Catalytic ReactionsClick Chemistry and Applications