Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3748-3759.DOI: 10.6023/cjoc202004008 Previous Articles     Next Articles


宋常华a,b, 沈许b, 于芳a, 何宇鹏a, 俞寿云b   

  1. a 辽宁石油化工大学化学化工与环境学部 辽宁抚顺 113001;
    b 南京大学化学化工学院 生命分析化学国家重点实验室 南京 210023
  • 收稿日期:2020-04-06 修回日期:2020-04-29 发布日期:2020-05-08
  • 通讯作者: 何宇鹏, 俞寿云;
  • 基金资助:

Generation and Application of Iminyl Radicals from Oxime Derivatives Enabled by Visible Light Photoredox Catalysis

Song Changhuaa,b, Shen Xub, Yu Fanga, He Yupenga, Yu Shouyunb   

  1. a College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun, Liaoning 113001;
    b State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023
  • Received:2020-04-06 Revised:2020-04-29 Published:2020-05-08
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21732003, 21978124) and the Innovative Talent Project of Educational Department of Liaoning Province (No. LR2018019).

The advent of visible light photoredox catalysis has transformed the way of single-electron transfer (SET) processes and accessing radical species. As a result, the chemistry of nitrogen-centered radicals has witnessed a remarkable gain in interest. Specifically, under visible light photoredox catalysis, iminyl radicals can be generated from oxime derivatives, such as O-acyl oximes, O-aryl oximes and α-imino-oxy acids. Meanwhile, the reactivity of iminyl radcials is investigated systematically. Iminyl radicals can undergo four major classes of reactions, namely addition to arenes, intramolecular hydrogen atom transfer and subsequent reactions, addition to alkenes, Norrish type-I fragmentation (cleavage of α-carbon-carbon bonds) and subsequent reactions. In this review, the most significant progresses in the use of oximes and their derivatives as iminyl precursors are discussed and their engagement in photoredox-mediated transformations is outlined.

Key words: nitrogen-centered radical, iminyl radical, photoredox catalysis, visible light