电化学介导的氧化羧化及二氧化碳还原羧化制备羧酸的研究进展

doi:10.6023/cjoc202311030

摘要/Abstract

作为常见的一类重要化合物, 羧酸被广泛应用于医药、农药和聚合物等领域, 因此, 探究高效且温和的羧酸合成方法具有重要意义. 电化学合成羧酸因其环境友好、条件温和等优点, 引起人们广泛关注. 根据反应机理不同, 主要从电化学氧化羧化、电化学二氧化碳还原羧化两方面出发, 对电化学合成羧酸这一领域近年来的相关研究做了综述.

关键词: 电化学, 羧酸, 氧化羧化, 还原羧化, 二氧化碳

As a class of common and important compounds, carboxylic acids are widely used in areas of medicine, pesticides and polymers. Therefore, development of facile and efficient methods for the synthesis of carboxylic acids is of great significance. Electrochemical synthesis of carboxylic acids has attracted widespread attentions due to its environmentally friendly and mild conditions. This article mainly reviews the relevant research in electrochemical synthesis of carboxylic acids in recent years from two aspects: electrochemical oxidation for carboxylation and electrochemical reduction of carbon dioxide for carboxylation.

Key words: electrochemistry, carboxylic acids, oxidative carboxylation, reductive carboxylation, carbon dioxide

引用此文

吕帅, 朱钢国, 姚金忠, 周宏伟. 电化学介导的氧化羧化及二氧化碳还原羧化制备羧酸的研究进展[J]. 有机化学, 2024, 44(3): 780-808.

Shuai Lv, Gangguo Zhu, Jinzhong Yao, Hongwei Zhou. Research Progress in Preparation of Carboxylic Acids by Electrochemical Mediated Oxidative Carboxylation and Reductive Carboxylation of Carbon Dioxide[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 780-808.

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图/表 41

图式1. 使用NiOOH作为阳极电化学氧化伯醇制羧酸

Scheme 1. Electrochemical oxidation of primary alcohol to carboxylic acid using NiOOH as anode

图式2. 使用负载了Mn掺杂CoOOH材料的泡沫镍作为阳极的醇、醛与酮的电化学氧化制羧酸

Scheme 2. Electrochemical oxidation of alcohols, aldehydes and ketones to carboxylic acids using nickel foam loaded with Mn-doped CoOOH material as anode

图式3. 使用CuOCoOOH作为阳极的醇、酮的电化学氧化

Scheme 3. Electrooxidation of alcohols and ketones using CuO- CoOOH as the anode

图式4. 使用ACT作为电氧化介质氧化伯醇与醛

Scheme 4. Primary alcohols and aldehydes oxidized using ACT as electrooxidation medium

图式5. 烯烃与环烯烃的电化学氧化裂解合成羧酸及反应机理

Scheme 5. Synthesis of carboxylic acid by electrochemical oxidative cracking of olefin and cycloolefin and reaction mechanism

图式6. 炔烃的电化学氧化裂解合成羧酸及反应机理

Scheme 6. Synthesis of carboxylic acid by electrochemical oxidative cracking of alkynes and its reaction mechanism

图式7. 偕二氟烯烃的二氧化碳电化学羧化及反应机理

Scheme 7. Carbon dioxide electrochemical carboxylation and reaction mechanism of difluoroalkenes

图式8. 偕二氟环丙烷的选择性电化学开环羧化及反应机理

Scheme 8. Selective electrochemical ring opening carboxylation and reaction mechanism of difluorocyclopropane

图式9. 三氟甲基芳烃的选择性电化学脱氟羧化反应

Scheme 9. Selective electrochemical defluorocarboxylation reaction of trifluoromethyl aromatic hydrocarbons

图式10. 苯基苄基砜的二氧化碳电羧化合成芳基乙酸及反应机理

Scheme 10. Carbon dioxide electrocarboxylation of phenyl benzyl sulfone to aryl acetic acid and reaction mechanism

图式11. 以α,β-不饱和砜为底物电化学合成α,β-不饱和羧酸

Scheme 11. α,β-unsaturated carboxylic acid was synthesized by electrochemical method using α,β-unsaturated sulfone as substrate

图式12. α,β-不饱和砜电羧化合成α,β-不饱和羧酸的反应机理

Scheme 12. Reaction mechanism of α,β-unsaturated sulfone electrocarboxylation to α,β-unsaturated carboxylic acid

图式13. 环烷烃的电化学开环二羧化及反应机理

Scheme 13. Electrochemical ring-opening dicarboxylation of cycloalkanes and its reaction mechanism

图式14. 非共轭二烯的电化学二羧化及反应机理

Scheme 14. Electrochemical dicarboxylation of unconjugated diene and its reaction mechanism

图式15. 烯烃的电还原羧化-烃基化反应及反应机理

Scheme 15. Electroreduction carboxylation alkylation reaction of olefins and its reaction mechanism

图式16. 具有低还原电势的芳香化合物的电化学去芳构双羧化及反应机理

Scheme 16. Electrochemical de aromatization and bicarboxylation of aromatic compounds with low reduction potential and reaction mechanism

图式17. 乙酸丙炔酯与二氧化碳的电羧化反应及反应机理

Scheme 17. Electrocarboxylation reaction and reaction mechanism of propargyl acetate with carbon dioxide

图式18. 两种环氧化物电羧化方案及反应机理

Scheme 18. Two electrocarboxylation schemes and reaction mechanisms of epoxides

图式19. 氮杂环丙烷衍生物的电化学开环羧化反应

Scheme 19. Electrochemical ring opening carboxylation reaction of nitrogen heterocyclic propane derivatives

图式20. 环酮肟酯的电化学开环羧化反应及反应机理

Scheme 20. Electrochemical ring-opening carboxylation of cycloketoxime esters and its mechanism

图式21. 对甲基苯醌电化学羧化合成4-羟基苯乙酸衍生物及反应机理

Scheme 21. Electrochemical carboxylation of p-methylbenzoquinone to 4-hydroxyphenylacetic acid derivatives and reaction mechanism

图式22. 不使用牺牲阳极的烯烃电化学羧化及反应机理

Scheme 22. Electrochemical carboxylation of olefin without sacrificial anodes and its reaction mechanism

图式23. 不使用牺牲阳极的共轭二烯烃的选择性电化学羧化及反应机理

Scheme 23. Selective electrochemical carboxylation and reaction mechanism of conjugated diolefins without sacrificial anodes

图式24. α,β-不饱和酸酯的电化学羧化

Scheme 24. Electrochemical carboxylation of α,β-unsaturated acid esters

图式25. 由苄卤制备的季铵盐的脱三甲胺电化学羧化及反应机理

Scheme 25. Electrochemical carboxylation and reaction mechanism of trimethylamine removal of quaternary ammonium salt prepared by benzyl halide

图式26. 使用溴化镁作为阳极牺牲剂的卤代烃的电化学羧化反应

Scheme 26. Electrochemical carboxylation of halogenated hydrocarbons using magnesium bromide as anode sacrificial agent

图式27. α-三氟甲基烯烃的选择性脱氟电羧化及反应机理

Scheme 27. Selective defluorinated electrocarboxylation of α-trifluoromethylolefin and reaction mechanism

图式28. 醛、酮的二氧化碳电羧化反应

Scheme 28. Carbon dioxide electrocarboxylation of aldehydes and ketones

图式29. N-酰基亚胺通过两种电羧化方案制备α-氨基酸衍生物及反应机理

Scheme 29. α-Amino acid derivatives prepared by N-acylimide through two kinds of electrocarboxylation schemes and the reaction mechanism

图式30. 不使用牺牲阳极的芳香化合物的选择性电羧化及反应机理

Scheme 30. Selective electrocarboxylation and reaction mechanism of aromatic compounds without sacrificial anodes

图式31. 氮杂芳烃的选择性电羧化及反应机理

Scheme 31. Selective electrocarboxylation of azaarenes and its reaction mechanism

图式32. 包括不饱和烃的电羧化、醇和胺的电氧化的成对电合成方案及反应机理

Scheme 32. Paired electrosynthesis schemes and reaction mechanisms including electrocarboxylation of unsaturated organic compounds, electro oxidation of alcohols and amines

图式33. 牺牲阳极的二价钐催化的芳基卤的电化学羧化及反应机理

Scheme 33. Electrochemical carboxylation and reaction mechanism of aryl halide catalyzed by samarium divalent with sacrificial anode

图式34. 二价钐催化的苄基卤的电化学羧化及反应机理

Scheme 34. Electrochemical carboxylation and reaction mechanism of benzyl halide catalyzed by samarium divalent

图式35. 二价钐催化的苯乙烯衍生物的电羧化及反应机理

Scheme 35. Electrocarboxylation and reaction mechanism of styrene derivatives catalyzed by samarium divalent

图式36. 钯配合物催化的羧酸烯丙酯的电羧化及反应机理

Scheme 36. Electrocarboxylation of allyl carboxylate catalyzed by palladium complexes and its reaction mechanism

图式37. 三苯基膦为配体的钴配合物催化烯丙基卤的脱卤电羧化及反应机理

Scheme 37. Dehalogenated electrocarboxylation of allyl halides catalyzed by cobalt complexes with triphenylphosphine as ligand and its reaction mechanism

图式38. dppm为配体的镍配合物催化的烯丙基卤的脱卤电羧化及反应机理

Scheme 38. Dehalogenated electrocarboxylation of allyl halides catalyzed by nickel complexes with dppm as ligands and its reaction mechanism

图式39. 镍配合物催化的芳基卤的电羧化及反应机理

Scheme 39. Electrocarboxylation and reaction mechanism of aryl halide catalyzed by nickel complexes

图式40. 萘介导的芳基卤电羧化合成芳基甲酸及反应机理

Scheme 40. Synthesis of aryl halide into aryl formic acid by naphthalene mediated carboxylation and reaction mechanism

图式41. 对三联苯介导的含吸电子取代基的萘衍生物电化学羧化及反应机理

Scheme 41. Electrochemical carboxylation of naphthalene derivatives with electron-absorbing substituents mediated by p-terphenyl and its reaction mechanism

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