电化学固定CO2构建羧酸衍生物的研究进展

doi:10.6023/cjoc202208004

有机化学 ›› 2023, Vol. 43 ›› Issue (4): 1416-1434.DOI: 10.6023/cjoc202208004 上一篇下一篇

综述与进展

电化学固定CO₂构建羧酸衍生物的研究进展

潘永周^a^,^b, 蒙秀金^b, 王迎春^c, 何慕雪^a^,^*()

a 桂林医学院公共卫生学院广西环境暴露组学与全生命周期健康重点实验室广西桂林 541199
b 广西师范大学化学与药学学院省部共建药用资源化学与药物分子工程国家重点实验室广西桂林 541004
c 吉首大学化学化工学院湖南吉首 416000

收稿日期:2022-08-03 修回日期:2022-10-11 发布日期:2022-11-15
通讯作者: 何慕雪
基金资助:
广西自然科学基金(2022GXNSFBA035489); 广西自然科学基金(2021GXNSFBA196041); 中央引导地方科技发展资金项目(桂科ZY21195014); “武陵山地区民族药解析与创制湖南省工程实验室”开放课题(hgxy2101)

Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives

Yongzhou Pan^a^,^b, Xiujin Meng^b, Yingchun Wang^c, Muxue He^a()

a Guangxi Key Laboratory of Environmental Exposomics and Entire Lifecycle Health, School of Public Health, Guilin Medical University, Guilin, Guangxi 541199
b State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004
c College of Chemistry and Chemical Engineering, Jishou University, Jishou, Hunan 416000

Received:2022-08-03 Revised:2022-10-11 Published:2022-11-15
Contact: Muxue He
Supported by:
Natural Science Foundation of Guangxi Province(2022GXNSFBA035489); Natural Science Foundation of Guangxi Province(2021GXNSFBA196041); Central Government Guides Local Science and Technology Development Fund Projects(guike ZY21195014); Opening Project of Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wuling Mountain(hgxy2101)

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摘要/Abstract

CO₂由于其含量丰富、无毒和低成本等特性可作为有机合成中的重要C1源, 因此, 使用CO₂作为C1源合成高附加值的化合物具有重要的意义. 本综述重点介绍了在电化学条件下使用CO₂作为亲电试剂参与有机化合物羧化反应的最新进展. 主要介绍了非活化有机卤化物、不饱和烯烃化合物和一些特殊化合物的电化学羧化, 并就使用和不使用牺牲阳极进行了详细分类, 讨论了这些反应的反应机制, 为今后此类反应在有机合成中的应用提供参考.

关键词: 二氧化碳, 羧化, 羧酸衍生物, 电化学合成

CO₂ is an important C1 source in organic synthesis due to its abundant, non-toxic and low-cost properties. There- fore, it is of great significance to use CO₂ as a C1 source to synthesize compounds with high added value. This review focuses on the recent progress in the carboxylation of organic compounds using CO₂ as an electrophile under electrochemical conditions. The electrochemical carboxylation of non-activated organic halides, unsaturated alkene compounds and some special compounds are mainly introduced. And the use of sacrificial anodes and non-sacrificial anodes is classified in detail. The reaction mechanisms of these reactions are also discussed. This review provides a reference for the application of such reactions in organic synthesis in the future.

Key words: carbon dioxide, carboxylation, carboxylic acid derivatives, electrochemical synthesis

引用此文

潘永周, 蒙秀金, 王迎春, 何慕雪. 电化学固定CO₂构建羧酸衍生物的研究进展[J]. 有机化学, 2023, 43(4): 1416-1434.

Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.

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图/表 32

Figure 1. Some representative drug molecules containing carboxylic acids

Scheme 1. Efficient electrochemical carboxylation of benzyl halides by using sacrificial-free anode

Scheme 2. CO2 immobilization on phenyl halides using a microreactor without sacrificial anode

Scheme 3. Direct electrochemical carboxylation of benzylic C—N bonds with CO2 by using sacrificial-free anode

Scheme 4. Mechanism of electrochemical carboxylation of phenyl and phenethylammonium salts

Scheme 5. Electroreductive carboxylation of organic halides by organic mediators

Scheme 6. CO2 activation by electrogenerated divalent samarium for aryl halide carboxylation

Scheme 7. Electrogenerated Sm(II)-catalyzed CO2 activation for carboxylation of benzyl halides

Scheme 8. Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2

Scheme 9. Selective α,δ-hydrocarboxylation of conjugated dienes utilizing CO2 and electrosynthesis. Regioselectivity 40/40' given in parentheses, only major products are shown

Scheme 10. Selective β-hydrocarboxylation of substituted alkenes

Scheme 11. Direct electrochemical defluorinative carboxylation of α-CF3 alkenes with CO2

Scheme 12. Reaction mechanism of direct electrochemical defluorocarboxylation dioxide of α-CF3 alkene with CO2

Scheme 13. Electrosynthesis all-carbon α-quaternary centered carboxylic acids from α,β-unsaturated esters

Scheme 14. Electroreductive carbofunctionalization of alkenes with alkyl bromides via a radical-polar crossover mechanism

Scheme 15. Direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with CO2

Scheme 16. Palladium-catalyzed reductive electrocarboxylation of allyl esters with carbon dioxide (regioselectivity 73/73' given in parentheses, only major products are shown)

Scheme 17. Electrochemically mediated enantioselective carboxylation of allyl acetate with CO2

Scheme 18. Reaction mechanism of palladium-catalyzed reductive electrocarboxylation of allyl esters with CO2

Scheme 19. Electroallylation of CO2 with chlorides at [Cu]@Ag cathode (regioselectivity 80/80' given in parentheses, only major products are shown)

Scheme 20. Electroreductive cobalt-catalyzed carboxylation of CO2 and allylic chlorides (regioselectivity 84/84' given in parentheses, only major products are shown)

Scheme 21. Nickel-catalyzed electrocarboxylation of allylic halides with CO2 (regioselectivity 91/91' given in parentheses, only major products are shown)

Scheme 22. Desulfonylative electrocarboxylation with CO2

Scheme 23. Synthesis of N-Boc-α-amino acids via electrochemical carboxylation of N-Boc-α-aminosulfones and CO2

Scheme 24. Synthesis of diacids via electrochemical ring-opening

Scheme 25. Derivatization and polymerization of 101g

Scheme 26. Synthesis of α-amino acids via electrochemical carboxylation of N-acylimines and CO2

Scheme 27. Synthesis of diacids via electrochemical carboxylation of heterocycles with highly negative reduction potentials

Scheme 28. Application of an electrochemical method for the carboxylation of heteroaromatics

Scheme 29. Synthesis of β-hydroxy acid via electrochemical carboxylation of aryl epoxides and CO2

Scheme 30. Reaction mechanism of electrocarboxylation of aryl epoxides and CO2

Scheme 31. Synthesis of β-hydroxy acid via electrochemical carboxylation of epoxides and CO2

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电化学固定CO₂构建羧酸衍生物的研究进展

Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives

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