A general 11C-labeling approach enabled by fluoride-mediated desilylation of organosilanes

Wenchao Qu (), Bao Hu, John W. Babich, Nicole Waterhouse, Marybeth Dooley, Shashikanth Ponnala and Julie Urgiles
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Wenchao Qu: Citigroup Biomedical Imaging Center, Weill Cornell Medicine
Bao Hu: Citigroup Biomedical Imaging Center, Weill Cornell Medicine
John W. Babich: Citigroup Biomedical Imaging Center, Weill Cornell Medicine
Nicole Waterhouse: Citigroup Biomedical Imaging Center, Weill Cornell Medicine
Marybeth Dooley: Citigroup Biomedical Imaging Center, Weill Cornell Medicine
Shashikanth Ponnala: Molecular Imaging Innovations Institute (MI3), Weill Cornell Medicine
Julie Urgiles: Molecular Imaging Innovations Institute (MI3), Weill Cornell Medicine

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Carbon-11 (11C) is one of the most ideal positron emitters for labeling bioactive molecules for molecular imaging studies. The lack of convenient and fast incorporation methods to introduce 11C into organic molecules often hampers the use of this radioisotope. Here, a fluoride-mediated desilylation (FMDS) 11C-labeling approach is reported. This method relies on thermodynamically favored Si-F bond formation to generate a carbanion, therefore enabling the highly efficient and speedy incorporation of [11C]CO2 and [11C]CH3I into molecules with diversified structures. It provides facile and rapid access to 11C-labeled compounds with carbon-11 attached at various hybridized carbons as well as oxygen, sulfur and nitrogen atoms with broad functional group tolerance. The exemplified syntheses of several biologically and clinically important radiotracers illustrates the potentials of this methodology.

Date: 2020
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DOI: 10.1038/s41467-020-15556-7

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