Key Laboratory of Functional Molecular Solids (Ministry of Education), Anhui Key Laboratory of Molecular Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.
Chem Commun (Camb). 2020 Mar 3;56(18):2775-2778. doi: 10.1039/d0cc00300j.
The expeditious construction of phenanthridine scaffolds via a Pd/MnO2-mediated C-H arylation/oxidative annulation cascade involving aldehydes, aryl iodides and amino acids is disclosed. This reaction proceeds smoothly involving the formation of multiple chemical bonds with the tolerance of a wide range of functional groups. The control experiments suggest a radical mechanism for C-N bond formation via MnO2-promoted oxidative annulation of imine compounds. The synthetic utility of this transformation has been demonstrated via the straightforward access to bioactive natural alkaloid trisphaeridine and its analogue.
本文报道了一种通过 Pd/MnO2 介导的 C-H 芳基化/氧化环化级联反应快速构建菲啶骨架的方法，该反应涉及醛、芳基碘化物和氨基酸。该反应能顺利进行，涉及到多种化学键的形成，对多种官能团具有很好的耐受性。控制实验表明，通过 MnO2 促进亚胺化合物的氧化环化，可以通过自由基机制形成 C-N 键。该转化的合成实用性已通过直接获得生物活性天然生物碱三尖杉宁碱及其类似物得到了证明。
