Huang Cheng, Wang Jing-Hao, Qiao Jia, Fan Xiu-Wei, Chen Bin, Tung Chen-Ho, Wu Li-Zhu
Key Laboratory of Photochemical Conversion and Optoelectronic Materials , Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, the Chinese Academy of Sciences , Beijing 100190 , P.R. China.
School of Future Technology , University of Chinese Academy of Science , Beijing 100049 , P.R. China.
J Org Chem. 2019 Oct 18;84(20):12904-12912. doi: 10.1021/acs.joc.9b01603. Epub 2019 Jul 25.
The functionalization of aliphatic C-H bonds is both a major challenge and a desirable goal in organic synthesis. Here, we describe the successful arylation of unactivated alkanes with heteroarenes by using iridium polypyridyl complexes as the photocatalyst and persulfate as the HAT catalyst precursor under visible-light irradiation. This reaction features good functional group tolerance and broad scope with regard to both alkane and heteroarene substrates (37 examples), which allows direct access to alkyl-substituted -heteroarenes, a key structural motif in natural products and bioactive molecules.
脂肪族碳氢键的官能团化在有机合成中既是一项重大挑战，也是一个理想目标。在此，我们描述了在可见光照射下，使用铱多吡啶配合物作为光催化剂、过硫酸盐作为氢原子转移（HAT）催化剂前体，成功实现未活化烷烃与杂芳烃的芳基化反应。该反应具有良好的官能团耐受性，对于烷烃和杂芳烃底物范围广泛（37个实例），能够直接得到烷基取代的杂芳烃，这是天然产物和生物活性分子中的关键结构单元。
