C–N Coupling via Antiaromatic Endocyclic Nitrenium Ions

Herein, we report a C–N coupling reaction via antiaromatic endocyclic nitrenium ions. The nitrenium ion intermediate was generated by a combination of iodine­(III) reagent PhI­(OCOCF3)2 and the N–H center of benzimidazole units at ambient laboratory conditions. Metal-free synthesis of benzimidazole-fused phenanthridine derivatives was achieved in good to excellent yields.

本文报道了一种基于反芳香性环内氮鎓离子（nitrenium ion）的C-N偶联反应。该氮鎓离子中间体可通过三价碘试剂PhI(OCOCF3)2与苯并咪唑单元的N-H中心在常温实验室条件下协同生成。本研究成功实现了苯并咪唑稠合菲啶衍生物的无金属合成，产物收率可达良好至优异水平。