Cu-Mediated C$$-$$H 18F-Fluorination of Electron-Rich (Hetero)arenes
Journal Article
·
· Organic Letters
- Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States
- Department of Radiology, University of Michigan, 1301 Catherine, Ann Arbor, Michigan 48109, United States
- Chemistry Capabilities and Screening, Merck Sharp &, Dohme, Kenilworth, New Jersey 07033, United States
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. Finally, 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.
- Research Organization:
- Univ. of Michigan, Ann Arbor, MI (United States)
- Sponsoring Organization:
- USDOE
- Grant/Contract Number:
- SC0012484
- OSTI ID:
- 1367716
- Alternate ID(s):
- OSTI ID: 1372897
- Journal Information:
- Organic Letters, Journal Name: Organic Letters; ISSN 1523-7060
- Publisher:
- American Chemical SocietyCopyright Statement
- Country of Publication:
- United States
- Language:
- English
Cited by: 64 works
Citation information provided by
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