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Cu-Mediated C-H 18 F-Fluorination of Electron-Rich (Hetero)arenes.
- Source :
-
Organic letters [Org Lett] 2017 Jul 21; Vol. 19 (14), pp. 3939-3942. Date of Electronic Publication: 2017 Jun 30. - Publication Year :
- 2017
-
Abstract
- This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp <superscript>2</superscript> )-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 [ <superscript>18</superscript> F]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 <superscript>18</superscript> F-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity.
- Subjects :
- Copper
Fluorine Radioisotopes
Halogenation
Molecular Structure
Electrons
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 19
- Issue :
- 14
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 28665619
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b01902