Yang Bin, Chansaenpak Kantapat, Wu Hongmiao, Zhu Lin, Wang Mengzhe, Li Zibo, Lu Hongjian
Institute of Chemistry & BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Chem Commun (Camb). 2017 Mar 25;53(24):3497-3500. doi: 10.1039/c7cc01393k. Epub 2017 Mar 10.
The intramolecular fluorocyclization of unsaturated carbamates is described here using a hypervalent iodine reagent in the presence of a silver catalyst. Both (hetero)aryl-substituted olefins and acrylamides can be utilized as effective substrates. Preliminary mechanistic investigations suggest that the reaction proceeds via a cyclization/1,2-(hetero)aryl migration/fluorination cascade involving an unusual radical process. Furthermore, starting from no-carrier-added [F]TBAF, a simple one-pot, two-step cascade method was developed for the generation of F-labeled heterocycles with high radiochemical purity.
本文描述了在银催化剂存在下，使用高价碘试剂进行不饱和氨基甲酸酯的分子内氟环化反应。（杂）芳基取代的烯烃和丙烯酰胺均可作为有效的底物。初步机理研究表明，该反应通过环化/1,2-（杂）芳基迁移/氟化级联反应进行，涉及一个不寻常的自由基过程。此外，从无载体添加的[F]TBAF出发，开发了一种简单的一锅两步级联方法，用于生成具有高放射化学纯度的F标记杂环。
