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

doi:10.6023/cjoc202004008

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

Special Issue: 有机光催化虚拟合辑；创刊四十周年专辑

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^a,b, 沈许^b, 于芳^a, 何宇鹏^a, 俞寿云^b

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 E-mail:yushouyun@nju.edu.cn;yupeng.he@lnpu.edu.cn
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.

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

Song Changhua^a,b, Shen Xu^b, Yu Fang^a, He Yupeng^a, Yu Shouyun^b

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

Cite this article

Song Changhua, Shen Xu, Yu Fang, He Yupeng, Yu Shouyun. Generation and Application of Iminyl Radicals from Oxime Derivatives Enabled by Visible Light Photoredox Catalysis[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3748-3759.

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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

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

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