Crown Ether Nucleophilic Catalysts (CENCs): Agents for Enhanced Silicon Radiofluorination.
New bifunctional phase transfer agents were synthesized and investigated for their abilities to promote rapid fluorination at silicon. These agents, dubbed crown ether nucleophilic catalysts (CENCs), are 18-crown-6 derivatives containing a side-arm and a potentially nucleophilic hydroxyl group. These CENCs proved efficacious in the fluorination of hindered silicon substrates, with fluorination yields dependent on the length of linker connecting the metal chelating unit to the hydroxyl group. The efficacy of these CENCs was also demonstrated for rapid radiofluorination under mild conditions for eventual application in molecular imaging with positron emission tomography (PET). The hydrolysis-resistant aryl silicon fragment is promising as a convenient synthon for labeling potential PET radiotracers.
Department of Chemistry and Biochemistry, Florida Atlantic University , Boca Raton, Florida 33431-0991, United States.
Susovan
S
Jana
Department of Chemistry and Biochemistry, Florida Atlantic University , Boca Raton, Florida 33431-0991, United States.
Mohammed H
MH
Al-Huniti
Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health , Bethesda, Maryland 20892-1003, United States.
Bo Yeun
BY
Yang
Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health , Bethesda, Maryland 20892-1003, United States.
Shuiyu
S
Lu
Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health , Bethesda, Maryland 20892-1003, United States.
Victor W
VW
Pike
Department of Chemistry and Biochemistry, Florida Atlantic University , Boca Raton, Florida 33431-0991, United States.
Salvatore D
0000-0002-8824-6114
SD
Lepore
D002384:Catalysis; D043844:Crown Ethers / Q000737:chemistry*; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D006868:Hydrolysis; D012825:Silicon / Q000737:chemistry*
D043844:Crown Ethers; D005462:Fluorine Radioisotopes; D012825:Silicon