Journal
ORGANIC LETTERS
Volume 19, Issue 14, Pages 3939-3942Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01902
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Funding
- Merck Sharp Dohme
- NIH [R01EB021155]
- DOE [DE-SC0012484]
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This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp(2))-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 [F-18]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 F-18-labeled nimesulide derivative in high (2800 +/- 700 Ci/mmol) specific activity.
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