Liu Lixia, Zhang Qijing, Wang Chengming
College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou, Guangdong511443, China.
Org Lett. 2022 Aug 19;24(32):5913-5917. doi: 10.1021/acs.orglett.2c02118. Epub 2022 Aug 4.
An -heterocyclic carbene-catalyzed oxidant-, metal- and light-free iminyl radical generation pathway stemming from the reaction of vinyl azide and α-bromo ester is uncovered. This newly developed methodology is successfully applied to the redox-neutral construction of a number of diversified phenanthridine derivatives with nice functional group compatibility. Insights from the mechanism study reveal that this NHC-catalyzed transformation potentially proceeds through an alkyl radical addition-initiated HAS process, with the iminyl radical as an active intermediate.
发现了一种由乙烯基叠氮化物和α-溴代酯反应产生的、无需氧化剂、金属和光的N-杂环卡宾催化的亚胺基自由基生成途径。这种新开发的方法已成功应用于多种具有良好官能团兼容性的菲啶衍生物的氧化还原中性构建。机理研究的结果表明，这种NHC催化的转化可能通过烷基自由基加成引发的HAS过程进行，其中亚胺基自由基为活性中间体。
