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Synthesis of 18F-Difluoromethylarenes from Aryl (Pseudo) Halides

MPG-Autoren
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Ritter,  Tobias
Department of Chemistry and Chemical Biology, Harvard University;
Division of Nuclear Medicine and Molecular Imaging & Gordon Center for Medical Imaging, Massachusetts General Hospital;
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zitation

Shi, H., Braun, A., Wang, L., Liang, S. H., Vasdev, N., & Ritter, T. (2016). Synthesis of 18F-Difluoromethylarenes from Aryl (Pseudo) Halides. Angewandte Chemie International Edition in English, (55), 10786-10790. doi:10.1002/anie.201604106.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-002B-7476-E
Zusammenfassung
A general method for the synthesis of [18F]difluoromethylarenes from [18F]fluoride for radiopharmaceutical discovery is reported. The method is practical, operationally simple, tolerates a wide scope of functional groups, and enables the labeling of a variety of arenes and heteroarenes with radiochemical yields (RCYs, not decaycorrected) from 10 to 60%. The 18F-fluorination precursors are readily prepared from aryl chlorides, bromides, iodides, and triflates. Seven 18F-difluoromethylarene drug analogues and radiopharmaceuticals including Claritin, fluoxetine (Prozac), and [18F]DAA1106 were synthesized to show the potential of the method for applications in PET radiopharmaceutical design.