Cu-Mediated C–H 18F-Fluorination of Electron-Rich (Hetero)arenes

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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.
Funding Information
  • Merck Sharp and Dohme United Kingdom
  • National Institute of Biomedical Imaging and Bioengineering (R01EB021155)
  • Office of Science (DE-SC0012484)

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