Synthesis of evodiamine and its derivatives through a visible- light-driven intramolecular C-N-cross-coupling reaction

Authors：Zhang, Linfeng; Chen, Dong; Zhou, Chao; Yin, Yutong; Wang, Guixia; Zhu, Qiping; Li, Shiqing^*; Kong, Xiangfei^*

Source：2023, 115: 154305.

DOI：10.1016/j.tetlet.2022.154305

• Intramolecular C-N cross coupling
• Evodiamine
• Quinazolinone alkaloids
• Photo-chemistry
• Hydrogen bonding facilitating

A visible-light-initiated C-N-cross-coupling reaction is described, featuring metal-free and photocata-lyst-free, at ambient temperature, with air as the oxidant and pinacolborane as the reducing agent. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position has a negligible influence on yields. Moreover, DFT calculations were conducted and the results matched the free radical reaction mechanism. The reaction provides a straight-forward and environment-friendly approach for the synthesis of evodiamine and its derivatives.

• Institution
  桂林理工大学