Research Progress in Preparation of Carboxylic Acids by Electrochemical Mediated Oxidative Carboxylation and Reductive Carboxylation of Carbon Dioxide

doi:10.6023/cjoc202311030

Abstract

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

Cite this article

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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Fig. & Tab. 41

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

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

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

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

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

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

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

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

Scheme 9. Selective electrochemical defluorocarboxylation reaction of trifluoromethyl aromatic hydrocarbons

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

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

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

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

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

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

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

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

Scheme 18. Two electrocarboxylation schemes and reaction mechanisms of epoxides

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

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

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

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

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

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

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

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

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

Scheme 28. Carbon dioxide electrocarboxylation of aldehydes and ketones

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

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

Scheme 31. Selective electrocarboxylation of azaarenes and its reaction mechanism

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

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

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

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

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

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

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

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

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

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

References 81

[1]	Leech M. C.; Lam K. Acc. Chem. Res. 2020, 53, 121. doi: 10.1021/acs.accounts.9b00586
[2]	Haushalter R. W.; Phelan R. M.; Hoh K. M.; Su C.; Wang G.; Baidoo E. E. K.; Keasling J. D. J. Am. Chem. Soc. 2017, 139, 4615. doi: 10.1021/jacs.6b11895 pmid: 28291347
[3]	Kumar A.; Yadav P. K.; Singh S.; Singh A. Env. Pollut. Bioavail. 2023, 35, 2242701. doi: 10.1080/26395940.2023.2242701
[4]	Wang J.-K.; Zhou Q.; Wang J.-P.; Yang S.; Li G. L. Colloids Surf., A 2019, 569, 52. doi: 10.1016/j.colsurfa.2019.02.050
[5]	Moon Y.-S.; Kim H.-M.; Chun H. S.; Lee S.-E. Food Control 2018, 88, 207. doi: 10.1016/j.foodcont.2018.01.017
[6]	Zimmerman J. B.; Anastas P. T.; Erythropel H. C.; Leitner W. Science 2020, 367, 397. doi: 10.1126/science.aay3060 pmid: 31974246
[7]	Lodh J.; Paul S.; Sun H.; Song L. Y.; Schöfberger W.; Roy S. Front. Chem. 2023, 10.
[8]	Yan M.; Kawamata Y.; Baran P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397
[9]	Kingston C.; Palkowitz M. D.; Takahira Y.; Vantourout J. C.; Peters B. K.; Kawamata Y.; Baran P. S. Acc. Chem. Res. 2020, 53, 72. doi: 10.1021/acs.accounts.9b00539
[10]	Leech M. C.; Lam K. Nat. Rev. Chem. 2022, 6, 275. doi: 10.1038/s41570-022-00372-y
[11]	Elgrishi N.; Rountree K. J.; McCarthy B. D.; Rountree E. S.; Eisenhart T. T.; Dempsey J. L. J. Chem. Educ. 2018, 95, 197. doi: 10.1021/acs.jchemed.7b00361
[12]	Heard D. M.; Lennox A. J. J. Angew. Chem., Int. Ed. 2020, 59, 18866. doi: 10.1002/anie.v59.43
[13]	Little R. D. J. Org. Chem. 2020, 85, 13375. doi: 10.1021/acs.joc.0c01408
[14]	Schotten C.; Nicholls T. P.; Bourne R. A.; Kapur N.; Nguyen B. N.; Willans C. E. Green Chem. 2020, 22, 3358. doi: 10.1039/D0GC01247E
[15]	Hatch C. E.; Chain W. J. ChemElectroChem 2023, 10, e202300140.
[16]	Senboku H. Chem. Rec. 2021, 21, 2354. doi: 10.1002/tcr.v21.9
[17]	Wang S. Y.; Feng T.; Wang Y. W.; Qiu Y. A. Chem.-Asian J. 2022, 17, e202200543. doi: 10.1002/asia.v17.17
[18]	Liu X.-F.; Zhang K.; Tao L.; Lu X.-B.; Zhang W.-Z. Green Chem. Eng. 2022, 3, 125. doi: 10.1016/j.gce.2021.12.001
[19]	Jud W.; Salazar C. A.; Imbrogno J.; Verghese J.; Guinness S. M.; Desrosiers J.-N.; Kappe C. O.; Cantillo D. Org. Process Res. Dev. 2022, 26, 1486. doi: 10.1021/acs.oprd.2c00064
[20]	Zhou H.; Li Z.; Xu S.-M.; Lu L.; Xu M.; Ji K.; Ge R.; Yan Y.; Ma L.; Kong X.; Zheng L.; Duan H. Angew. Chem., Int. Ed. 2021, 60, 8976. doi: 10.1002/anie.v60.16
[21]	Liu S.; Dou S.; Meng J.; Liu Y.; Liu Y.; Yu H. Appl. Catal. B 2023, 331, 122709. doi: 10.1016/j.apcatb.2023.122709
[22]	Goloviznina K.; Salanne M. J. Phys. Chem. B 2023, 127, 742. doi: 10.1021/acs.jpcb.2c07238
[23]	Rafiee M.; Konz Z. M.; Graaf M. D.; Koolman H. F.; Stahl S. S. ACS Catal. 2018, 8, 6738. doi: 10.1021/acscatal.8b01640
[24]	Rafiee M.; Alherech M.; Karlen S. D.; Stahl S. S. J. Am. Chem. Soc. 2019, 141, 15266. doi: 10.1021/jacs.9b07243
[25]	Fisher T. J.; Dussault P. H. Tetrahedron 2017, 73, 4233. doi: 10.1016/j.tet.2017.03.039
[26]	Chan A. P. Y.; Sergeev A. G. Coord. Chem. Rev. 2020, 413, 213213. doi: 10.1016/j.ccr.2020.213213
[27]	Bäumer U. S.; Schäfer H. J. Electrochim. Acta 2003, 48, 489. doi: 10.1016/S0013-4686(02)00715-6
[28]	Bäumer U. S.; Schäfer H. J. J. Appl. Electrochem. 2005, 35, 1283. doi: 10.1007/s10800-005-9060-4
[29]	Nikl J.; Hofman K.; Mossazghi S.; Möller I. C.; Mondeshki D.; Weinelt F.; Baumann F.-E.; Waldvogel S. R. Nat. Commun. 2023, 14, 4565. doi: 10.1038/s41467-023-40259-0
[30]	Feng Q.; Wang Y.; Zheng B.; Huang S. Org. Lett. 2023, 25, 293. doi: 10.1021/acs.orglett.2c04204
[31]	Mena S.; Peral J.; Guirado G. Curr. Opin. Electrochem. 2023, 42, 101392.
[32]	Yu Z.; Shi M. Chem. Commun. 2022, 58, 13539. doi: 10.1039/D2CC05242C
[33]	Zhao Y.; Guo X.; Li S.; Fan Y.; Ji G.-C.; Jiang M.; Yang Y.; Jiang Y.-Y. Angew. Chem., Int. Ed. 2022, 61, e202213636. doi: 10.1002/anie.v61.48
[34]	Yao H.; Wang M.-Y.; Yue C.; Feng B.; Ji W.; Qian C.; Wang S.; Zhang S.; Ma X. Trans. Tianjin Univ. 2023, 29, 254. doi: 10.1007/s12209-023-00361-2
[35]	Senboku H. Chem. Rec. 2021, 21, 2354. doi: 10.1002/tcr.v21.9
[36]	Ran C.-K.; Liao L.-L.; Gao T.-Y.; Gui Y.-Y.; Yu D.-G. Curr. Opin. Green Sust. Chem. 2021, 32, 100525.
[37]	Chantarojsiri T.; Soisuwan T.; Kongkiatkrai P. Chin. J. Catal. 2022, 43, 3046. doi: 10.1016/S1872-2067(22)64180-9
[38]	Senboku H.; Katayama A. Curr. Opin. Green Sust. Chem. 2017, 3, 50.
[39]	Mao B.; Wei J.-S.; Shi M. Chem. Commun. 2022, 58, 9312. doi: 10.1039/D2CC03380A
[40]	Huang W.; Lin J.; Deng F.; Zhong H. Asian J. Org. Chem. 2022, 11, e202200220. doi: 10.1002/ajoc.v11.7
[41]	Zhang Z.; Ye J.-H.; Ju T.; Liao L.-L.; Huang H.; Gui Y.-Y.; Zhou W.-J.; Yu D.-G. ACS Catal. 2020, 10, 10871. doi: 10.1021/acscatal.0c03127
[42]	Fan Z.; Zhang Z.; Xi C. ChemSusChem 2020, 13, 6201. doi: 10.1002/cssc.v13.23
[43]	Saini S.; Prajapati P. K.; Jain S. L. Catal. Rev. 2022, 64, 631. doi: 10.1080/01614940.2020.1831757
[44]	Wang S.; Du G.; Xi C. Org. Biomol. Chem. 2016, 14, 3666. doi: 10.1039/C6OB00199H
[45]	Zhang L.; Hou Z. Curr. Opin. Green Sust. Chem. 2017, 3, 17.
[46]	Tortajada A.; Juliá-Hernández F.; Börjesson M.; Moragas T.; Martin R. Angew. Chem., Int. Ed. 2018, 57, 15948. doi: 10.1002/anie.v57.49
[47]	Xie S.-L.; Gao X.-T.; Wu H.-H.; Zhou F.; Zhou J. Org. Lett. 2020, 22, 8424. doi: 10.1021/acs.orglett.0c03051
[48]	Zhao B.; Pan Z.; Pan J.; Deng H.; Bu X.; Ma M.; Xue F. Green Chem. 2023, 25, 3095. doi: 10.1039/D2GC04636A
[49]	Mondal S.; Sarkar S.; Wang J. W.; Meanwell M. W. Green Chem. 2023, 25, 9075. doi: 10.1039/D3GC03387B
[50]	Zhong J.-S.; Yang Z.-X.; Ding C.-L.; Huang Y.-F.; Zhao Y.; Yan H.; Ye K.-Y. J. Org. Chem. 2021, 86, 16162. doi: 10.1021/acs.joc.1c01261
[51]	Yang Z.-X.; Lai L.; Chen J.; Yan H.; Ye K.-Y.; Chen F.-E. Chin. Chem. Lett. 2023, 34, 107956. doi: 10.1016/j.cclet.2022.107956
[52]	Liao L.-L.; Wang Z.-H.; Cao K.-G.; Sun G.-Q.; Zhang W.; Ran C.-K.; Li Y.; Chen L.; Cao G.-M.; Yu D.-G. J. Am. Chem. Soc. 2022, 144, 2062. doi: 10.1021/jacs.1c12071
[53]	Zhang W.; Liao L.-L.; Li L.; Liu Y.; Dai L.-F.; Sun G.-Q.; Ran C.-K.; Ye J.-H.; Lan Y.; Yu D.-G. Angew. Chem., Int. Ed. 2023, 62, e202301892. doi: 10.1002/anie.v62.23
[54]	Zhang W.; Lin S. J. Am. Chem. Soc. 2020, 142, 20661. doi: 10.1021/jacs.0c08532 pmid: 33231074
[55]	You Y.; Kanna W.; Takano H.; Hayashi H.; Maeda S.; Mita T. J. Am. Chem. Soc. 2022, 144, 3685. doi: 10.1021/jacs.1c13032
[56]	Qin J.-H.; Xiong Z.-Q.; Cheng C.; Hu M.; Li J.-H. Org. Lett. 2023, 25, 9176. doi: 10.1021/acs.orglett.3c03735
[57]	Zhang K.; Ren B.-H.; Liu X.-F.; Wang L.-L.; Zhang M.; Ren W.-M.; Lu X.-B.; Zhang W.-Z. Angew. Chem., Int. Ed. 2022, 61, e202207660. doi: 10.1002/anie.v61.38
[58]	Wang Y.; Tang S.; Yang G.; Wang S.; Ma D.; Qiu Y. Angew. Chem., Int. Ed. 2022, 61, e202207746. doi: 10.1002/anie.v61.38
[59]	Yang G.; Wang Y.; Qiu Y. Chem. Eur. J. 2023, 29, e202300959. doi: 10.1002/chem.v29.36
[60]	Liu X.-F.; Zhang K.; Wang L.-L.; Wang H.; Huang J.; Zhang X.-T.; Lu X.-B.; Zhang W.-Z. J. Org. Chem. 2023, 88, 5212. doi: 10.1021/acs.joc.2c01816
[61]	Yan Y.; Li H.; Xie F.; Lu W.; Zhang Z.; Jing L.; Han P. Adv. Synth. Catal. 2023, 365, 3830. doi: 10.1002/adsc.v365.22
[62]	Alkayal A.; Tabas V.; Montanaro S.; Wright I. A.; Malkov A. V.; Buckley B. R. J. Am. Chem. Soc. 2020, 142, 1780. doi: 10.1021/jacs.9b13305 pmid: 31960672
[63]	Sheta A. M.; Mashaly M. A.; Said S. B.; Elmorsy S. S.; Malkov A. V.; Buckley B. R. Chem. Sci. 2020, 11, 9109. doi: 10.1039/D0SC03148H
[64]	Sheta A. M.; Alkayal A.; Mashaly M. A.; Said S. B.; Elmorsy S. S.; Malkov A. V.; Buckley B. R. Angew. Chem., Int. Ed. 2021, 60, 21832. doi: 10.1002/anie.v60.40
[65]	Yang D.-T.; Zhu M.; Schiffer Z. J.; Williams K.; Song X.; Liu X.; Manthiram K. ACS Catal. 2019, 9, 4699. doi: 10.1021/acscatal.9b00818
[66]	Corbin N.; Yang D.-T.; Lazouski N.; Steinberg K.; Manthiram K. Chem. Sci. 2021, 12, 12365. doi: 10.1039/D1SC02413B
[67]	Gao X.-T.; Zhang Z.; Wang X.; Tian J.-S.; Xie S.-L.; Zhou F.; Zhou J. Chem. Sci. 2020, 11, 10414. doi: 10.1039/D0SC04091F
[68]	Seidler J.; Roth A.; Vieira L.; Waldvogel S. R. ACS Sustain. Chem. Eng. 2023, 11, 390. doi: 10.1021/acssuschemeng.2c06046
[69]	Zhang K.; Liu X.-F.; Zhang W.-Z.; Ren W.-M.; Lu X.-B. Org. Lett. 2022, 24, 3565. doi: 10.1021/acs.orglett.2c01267 pmid: 35532347
[70]	Zhao Z.; Liu Y.; Wang S.; Tang S.; Ma D.; Zhu Z.; Guo C.; Qiu Y. Angew. Chem., Int. Ed. 2023, 62, e202214710. doi: 10.1002/anie.v62.3
[71]	Sun G.-Q.; Yu P.; Zhang W.; Zhang W.; Wang Y.; Liao L.-L.; Zhang Z.; Li L.; Lu Z.; Yu D.-G.; Lin S. Nature 2023, 615, 67. doi: 10.1038/s41586-022-05667-0
[72]	Zhang X.; Li Z. H.; Chen H. S.; Shen C. R.; Wu H. H.; Dong K. W. ChemSusChem 2023, 16, e202300807. doi: 10.1002/cssc.v16.19
[73]	Bazzi S.; Le Duc G.; Schulz E.; Gosmini C.; Mellah M. Org. Biomol. Chem. 2019, 17, 8546. doi: 10.1039/C9OB01752F
[74]	Bazzi S.; Schulz E.; Mellah M. Org. Lett. 2019, 21, 10033. doi: 10.1021/acs.orglett.9b03927
[75]	Bazzi S.; Hu L.; Schulz E.; Mellah M. Organometallics 2023, 42, 1425-1431. doi: 10.1021/acs.organomet.3c00076
[76]	Jiao K.-J.; Li Z.-M.; Xu X.-T.; Zhang L.-P.; Li Y.-Q.; Zhang K.; Mei T.-S. Org. Chem. Front. 2018, 5, 2244. doi: 10.1039/C8QO00507A
[77]	Ang N. W. J.; Oliveira J. C. A.; Ackermann L. Angew. Chem., Int. Ed. 2020, 59, 12842. doi: 10.1002/anie.v59.31
[78]	Wu L.-X.; Deng F.-J.; Wu L.; Wang H.; Chen T.-J.; Guan Y.-B.; Lu J.-X. New J. Chem. 2021, 45, 13137. doi: 10.1039/D1NJ02006D
[79]	Sun G.-Q.; Zhang W.; Liao L.-L.; Li L.; Nie Z.-H.; Wu J.-G.; Zhang Z.; Yu D.-G. Nat. Commun. 2021, 12, 7086. doi: 10.1038/s41467-021-27437-8
[80]	Wang Y. W.; Zhao Z. W.; Pan D.; Wang S. Y.; Jia K. P.; Ma D. K.; Yang G. Q.; Xue X. S.; Qiu Y. A. Angew. Chem., Int. Ed. 2022, 61, e202210201. doi: 10.1002/anie.v61.41
[81]	Rawat V. K.; Hayashi H.; Katsuyama H.; Mangaonkar S. R.; Mita T. Org. Lett. 2023, 25, 4231 doi: 10.1021/acs.orglett.3c01033

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