有机电化学合成的研究进展

doi:10.6023/A22060260

化学学报 ›› 2022, Vol. 80 ›› Issue (8): 1115-1134.DOI: 10.6023/A22060260 上一篇下一篇

综述

有机电化学合成的研究进展

王振华^a, 马聪^a, 方萍^a, 徐海超^b^,^*(), 梅天胜^a^,^*()

a 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
b 厦门大学化学化工学院厦门 361005

投稿日期:2022-06-14 发布日期:2022-09-01
通讯作者: 徐海超, 梅天胜

作者简介:

王振华, 上海有机化学研究所博士后, 2013本科毕业于延安大学, 2016年在陕西师范大学获得硕士学位, 2019年在日本Okayama University取得博士学位. 目前在有机所梅天胜课题组从事有机电化学合成方法学的研究.

马聪, 中国科学院上海有机化学研究所助理研究员, 2010本科毕业于曲阜师范大学, 2015年在南开大学获得博士学位, 2016年在梅天胜课题组进行博士后研究, 主要从事有机电化学合成方法学的研究, 2020年进入梅天胜课题组继续从事有机电化学相关研究.

方萍, 中国科学院上海有机化学研究所副研究员, 2004本科毕业于兰州大学. 2010年在中国科学院上海有机化学研究所获得博士学位. 2010年3月~2011年2月在美国Indiana University-Purdue University Indianapolis从事博士后研究; 2010年2月~2012年5月在美国Indiana University (Bloomington)从事博士后研究. 2012年8月加入中科院上海有机化学研究所担任副研究员, 目前在梅天胜课题组从事过渡金属催化的有机化学反应研究.

徐海超, 教授, 博士生导师, 闽江学者特聘教授, 2006本科毕业于厦门大学, 同年赴美国Washington University师从Kevin D. Moeller教授, 并于2010年获得博士学位. 2011年在美国Yale University Jonathan A. Ellman课题组开展博士后研究工作, 2013年回到厦门大学开始独立研究工作. 他的研究兴趣是有机合成电化学和自由基化学.

梅天胜, 中国科学院上海有机化学研究所研究员、博士生导师. 2001年本科毕业于兰州大学, 2007年获得Brandeis硕士学位, 2012年获得Scripps研究所博士学位, 师从余金权教授. 同年在Utah大学Matthew Sigman课题组进行博士后研究工作. 于2014年回到上海有机化学研究所金属有机化学国家重点实验室开始独立研究工作, 从事金属有机电化学合成方面的研究.

基金资助:
中国科技部重点研发计划(2021YFA1500100); 国家自然科学基金(91956112); 国家自然科学基金(21572245); 及上海市科委基础研究项目(17JC1401200); 及上海市科委基础研究项目(18JC1415600)

Advances in Organic Electrochemical Synthesis

Zhenhua Wang^a, Cong Ma^a, Ping Fang^a, Haichao Xu^b(), Tiansheng Mei^a()

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

Received:2022-06-14 Published:2022-09-01
Contact: Haichao Xu, Tiansheng Mei
Supported by:
National Key Research & Development Program of China(2021YFA1500100); National Natural Science Foundation of China(91956112); National Natural Science Foundation of China(21572245); Program of Shanghai Science and Technology Committee(17JC1401200); Program of Shanghai Science and Technology Committee(18JC1415600)

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摘要/Abstract

有机电化学合成已成为一种实用、环境友好的合成方法, 广泛应用于氧化、还原以及氧化还原中性反应. 通过精准调控电流或者电位可在温和反应条件下实现一些具有挑战性的化学转化. 然而, 有机电化学反应也存在电极钝化、反应类型受限以及反应活性和选择性不易调控等难题. 日益紧张的能源和环境问题使得电化学合成近年来备受关注. 该综述的主要对象为有机溶液体系中的电化学合成, 从直接电解和间接电解两方面阐述近年来为解决这些难题所取得的进展. 在直接电解方面主要是通过合理的有机电化学反应设计、改变电解模式及设备或者将电化学技术与其它的化学合成技术相融合, 解决电极钝化、反应类型受限等问题. 在间接电解方面主要是利用有机分子或者过渡金属作为分子电催化剂去调控电极和底物之间的电子转移以及反应选择性, 实现一些选择性可控的化学转化.

关键词: 有机电化学合成, 氧化还原反应, 选择性转化, 直接电解, 间接电解

Organic electrochemical synthesis has become a useful and environmentally friendly alternative to traditional organic synthesis and has been applied to oxidation, reduction, or redox neutral transformation. By dialing in the electric current or electrode potential, it is possible to achieve some challenging transformations under mild reaction conditions. With the increasing awareness of energy efficiency and environmental protection, organic electrochemical synthesis has attracted much attention in recent years. However, electrochemical synthesis faces several challenges including electrode passivation, limited reaction types, the difficulty of controlling reactivity and selectivity, and so on. This review focuses on electrochemical synthesis in organic solution system, and it summarizes recent efforts in addressing these challenges through direct electrolysis and indirect electrolysis. In direct electrolysis, the strategies include the rational design of electrochemical electrolysis reactions, change of electrochemical electrolysis modes and equipment, or merging of electrochemical technology with other novel synthetic technologies. In terms of indirect electrolysis, organic compounds or transition metals are mainly used as molecular electrocatalysts to shuttle the electrons between electrodes and substrates and control the reaction reactivity and selectivity, affording some challenging chemical transformations.

Key words: organic electrochemical synthesis, redox reaction, selective transformation, direct electrolysis, indirect electrolysis

引用此文

王振华, 马聪, 方萍, 徐海超, 梅天胜. 有机电化学合成的研究进展[J]. 化学学报, 2022, 80(8): 1115-1134.

Zhenhua Wang, Cong Ma, Ping Fang, Haichao Xu, Tiansheng Mei. Advances in Organic Electrochemical Synthesis[J]. Acta Chimica Sinica, 2022, 80(8): 1115-1134.

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图/表 19

图1. 有机电化学合成的代表性工作

Figure 1. Representative examples of organic electrochemical synthesis

图2. 电化学反应设备和基本参数

Figure 2. Devices and basic parameters of electrochemical reactions

图3. 化学氧化还原和电氧化还原

Figure 3. Chemical redox and electrochemical redox

图4. 电化学的电解模式

Figure 4. Electrolytic mode of electrochemistry

图5. 上海有机化学研究所早期在电化学合成方面的代表性工作

Figure 5. Early representative work on electrochemical synthesis from SIOC

图6. 直接电解的代表性工作

Figure 6. Representative work on direct electrolysis in China

图7. 不同类型的成对电解反应

Figure 7. Different types toward paired electrolysis

图8. 流体电化学

Figure 8. Continuous-flow electrochemistry

图9. 光电催化的芳基碳氢键官能化反应

Figure 9. Photoelectrocatalytic C—H functionalizations of arenes

图10. 上海有机所早期在金属有机电化学合成的代表性工作

Figure 10. Early representative work on organometallic electrochemical synthesis from SIOC

图11. 卤素介导的电解过程

Figure 11. Halogen mediated electrolysis process

图12. 三芳基胺催化的电解过程

Figure 12. Triarylamine-catalyzed electrolysis process

图13. 二茂铁催化的电解过程

Figure 13. Ferrocene-catalyzed electrolysis process

图14. TEMPO催化的电化学C—H官能化反应

Figure 14. TEMPO-catalyzed electrochemical C—H functionalizations

图15. 过渡金属催化的电化学C(sp3)—H官能化反应

Figure 15. Transition metal-catalyzed electrochemical C(sp3)—H functionalizations

图16. 过渡金属催化的电化学C(sp2)—H官能化反应

Figure 16. Transition metal-catalyzed electrochemical C(sp2)—H functionalizations

图17. 过渡金属催化的区域选择性转化

Figure 17. Transition metal-catalyzed regioselective transformations

图18. 过渡金属催化的立体选择性转化

Figure 18. Transition metal-catalyzed enantioselective transformations

图19. 电化学促进的过渡金属催化的硫化和胺化反应

Figure 19. Transition metal-catalyzed electrochemical thiolation and amination

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有机电化学合成的研究进展

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