Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4014-4020.DOI: 10.6023/cjoc202105046 Previous Articles     Next Articles

ARTICLES

芳基碘介导的缺电子烯烃电化学氮杂环丙烷化反应

刘峰, 戴洁*(), 程旭*   

  1. 南京大学化学化工学院 化学与生物医学科学研究所 江苏省先进有机材料重点实验室国家级化学实验教学示范中心 南京 210023
  • 收稿日期:2021-05-27 修回日期:2021-07-06 发布日期:2021-07-19
  • 通讯作者: 戴洁, 程旭
  • 基金资助:
    国家自然科学基金(22071105); 国家自然科学基金(22031008)

Aryl-Iodide-Mediated Electrochemical Aziridination of Electron-Deficient Alkenes

Feng Liu, Jie Dai(), Xu Cheng   

  1. National Demonstration Center for Experimental Chemistry Education, Jiangsu Key Laboratory of Advanced Organic Materials, Institute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023
  • Received:2021-05-27 Revised:2021-07-06 Published:2021-07-19
  • Contact: Jie Dai, Xu Cheng
  • Supported by:
    National Natural Science Foundation of China(22071105); National Natural Science Foundation of China(22031008)

A protocol of electrochemical aziridination of electron-deficient alkenes was reported using phthalhydrazide as nitrogen source. The reaction could be conducted in undivided cell, and the ArI is essential to achieve the transformation. Hypervalent-iodine-stablized nitrene and acetyl hydroxyhydrazine were suggested as the in-situ generated nitrogen source for the stepwise aziridination. This protocol can be applied to the azirdination of α,β-unsaturated esters, amides, nitrile and ketones to give a series N-containing molecules.

Key words: electrochemistry, aziridination, hypervalent iodine, electron-deficient alkene