A universal procedure for the [¹⁸F]trifluoromethylation of aryl iodides and aryl boronic acids with highly improved specific activity.

Abstract

Herein, we describe a valuable method for the introduction of the [(18)F]CF3 group into arenes with highly improved specific activity by the reaction of [(18)F]trifluoromethane with aryl iodides or aryl boronic acids. This [(18)F]trifluoromethylation reaction is the first to be described in which the [(18)F]CF3 products are generated in actual trace amounts and can therefore effectively be used as PET tracers. The method shows broad scope with respect to possible aryl iodide and aryl boronic acid substrates, as well as good to excellent conversion. In particular, the [(18)F]trifluoromethylation of boronic acids was found to outperform [(18)F]trifluoromethylation reactions of halogenated aryl precursors with regard to conversion, reaction conditions, and kinetics.

• Authors: Dion van der Born, Claudia Sewing, J Koos D M Herscheid, Albert D Windhorst, Romano V A Orru, Danielle J Vugts
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 53 Issue 41 Pg. 11046-50 (Oct 06 2014) ISSN: 1521-3773 [Electronic] Germany
• PMID: 25155042 (Publication Type: Journal Article)
• Copyright: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Boronic Acids
• Chlorofluorocarbons, Methane
• Fluorine Radioisotopes
• Iodides
• Radiopharmaceuticals
• fluoroform

Topics

• Boronic Acids (chemistry)
• Chlorofluorocarbons, Methane (chemistry)
• Fluorine Radioisotopes (chemistry)
• Humans
• Iodides (chemistry)
• Isotope Labeling
• Neoplasms (diagnosis)
• Positron-Emission Tomography
• Radiopharmaceuticals (chemistry)