1. Cu-Mediated C-H 18F-Fluorination of Electron-Rich (Hetero)arenes.
- Author
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McCammant, Matthew S., Thompson, Stephen, Brooks, Allen F., Krska, Shane W., Scott, Peter J. H., and Sanford, Melanie S.
- Subjects
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AROMATIC compounds , *FLUORINATION , *IODONIUM salts , *NIMESULIDE , *ELECTRONS - Abstract
This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp²)-H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in a Cu-mediated radiofluorination with [18F]KF. This approach leverages the stability and availability of electron-rich arene starting materials to enable mild late-stage radiofluorination of toluene, anisole, aniline, pyrrole, and thiophene derivatives. The radiofluorination has been automated to access a 41 mCi dose of an 18F-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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