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.
Org Lett. 2017 Jul 21;19(14):3939-3942. doi: 10.1021/acs.orglett.7b01902. Epub 2017 Jun 30.
This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp)-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]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-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity.
本通讯描述了一种富电子芳环亲核放射性氟化的方法。该反应涉及先用 MesI(OH)OTs 对富电子芳环进行初始的 C(sp)-H 官能化，形成 (mesityl)(aryl)碘鎓盐。然后，该盐在原位与 [F]KF 进行 Cu 介导的放射性氟化。这种方法利用富电子芳环起始原料的稳定性和易得性，实现了温和的甲苯、苯甲醚、苯胺、吡咯和噻吩衍生物的晚期放射性氟化。该放射性氟化已被自动化，以高（2800 ± 700 Ci/mmol）比活度获得了 41 mCi 剂量的 F 标记尼美舒利衍生物。
Zotero 插件
