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2020 , Vol. 40 >Issue 11: 3748 - 3759

DOI: https://doi.org/10.6023/cjoc202004008

综述与进展

光氧化还原催化下以肟的衍生物作为前体亚胺自由基的产生及其反应

  • 宋常华 ,
  • 沈许 ,
  • 于芳 ,
  • 何宇鹏 ,
  • 俞寿云
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  • 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

  网络出版日期: 2020-05-08

基金资助

国家自然科学基金（Nos.21732003，21978124）和辽宁省教育厅高等学校创新人才（No.LR2018019）资助项目.

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

  • Song Changhua ,
  • Shen Xu ,
  • Yu Fang ,
  • He Yupeng ,
  • Yu Shouyun
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  • 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 date: 2020-04-06

  Revised date: 2020-04-29

  Online 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).

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摘要

在可见光氧化还原催化的条件下，从肟的衍生物（O-酰基肟、O-芳基肟和α-亚胺氧杂酸等）出发，高效清洁地产生了亚胺自由基.这方法促进了亚胺自由基反应活性的系统研究.亚胺自由基主要有以下4种反应模式：（1）对芳烃的加成反应，（2）分子内的氢迁移，（3）对烯烃的加成反应，（4）Norrish-I型断裂（α-位的碳-碳键断裂）反应.综述了近几年来在光氧化还原催化的条件下，以肟的衍生物作为前体，亚胺自由基的产生及其参与的典型反应.

关键词： 氮自由基; 亚胺自由基; 光氧化还原催化; 可见光

本文引用格式

宋常华 , 沈许 , 于芳 , 何宇鹏 , 俞寿云 . 光氧化还原催化下以肟的衍生物作为前体亚胺自由基的产生及其反应[J]. 有机化学, 2020 , 40(11) : 3748 -3759 . DOI: 10.6023/cjoc202004008

Abstract

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

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