Department of Chemistry and Chemical Biology, Indiana University─Purdue University Indianapolis, Indianapolis, Indiana 46202, United States.
Org Lett. 2022 Jan 28;24(3):916-920. doi: 10.1021/acs.orglett.1c04267. Epub 2022 Jan 13.
Polyfluoroarene moieties are of interest in medicinal chemistry, agrochemicals, and material sciences. Herein, we present the first polyfluoroarylation of unactivated alkyl halides via a halogen atom transfer process. This method converts primary, secondary, and tertiary alkyl halides into the respective polyfluoroaryl compounds in good yields in the presence of amide, carbamate, ester, aromatic, and sulfonamide moieties, including derivatives of complex bioactive molecules. Mechanistic work revealed that this transformation proceeds through an alkyl radical generated after the halogen atom transfer.
多氟芳烃部分在药物化学、农用化学品和材料科学中很有研究价值。在此，我们首次通过卤原子转移过程实现了对未活化的烷基卤化物的多氟芳基化。该方法在酰胺、碳酸酯、酯、芳基和磺酰胺等基团存在下，包括复杂生物活性分子的衍生物，可将伯、仲和叔烷基卤化物转化为相应的多氟芳基化合物，产率良好。机理研究表明，该转化是通过卤原子转移后生成的烷基自由基进行的。
