Skip to main content

Advertisement

SpringerLink
Log in

Electrocarboxylation of CO2 with Organic Substrates: Toward Cathodic Reaction

  • Review
  • Published:
Transactions of Tianjin University Aims and scope Submit manuscript

Abstract

Electrocarboxylation of carbon dioxide (CO2) using organic substrates has emerged as a promising method for the sustainable synthesis of value-added carboxylic acids due to its renewable energy source and mild reaction conditions. The reactivity and product selectivity of electrocarboxylation are highly dependent on the cathodic behavior, involving a sequence of electron transfers and chemical reactions. Hence, it is necessary to understand the cathodic reaction mechanisms for optimizing reaction performance and product distribution. In this work, a review of recent advancements in the electrocarboxylation of CO2 with organic substrates based on different cathodic reaction pathways is presented to provide a reference for the development of novel methodologies of CO2 electrocarboxylation. Herein, cathodic reactions are particularly classified into two categories based on the initial electron carriers (i.e., CO2 radical anion and substrate radical anion). Furthermore, three cathodic pathways (ENE(N), ENED, and EDEN) of substrate radical anion-induced electrocarboxylation are discussed, which differ in their electron transfer sequence, substrate dissociation, and nucleophilic reaction, to highlight their implications on reactivity and product selectivity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Reproduced with permission from Ref. [50]. Copyright 2019 Royal Society of Chemistry. b In situ electrogenerated SmII reduced CO2 electrocarboxylation. Reproduced with permission from Ref. [53]. Copyright 2019 American Chemical Society

Fig. 3

Reproduced with permission from Ref. [22]. Copyright 2022 American Chemical Society

Fig. 4

Reproduced with permission from Ref. [59]. Copyright 2019 WILEY VCH

Fig. 5

Reproduced with permission from Ref. [59]. Copyright 2019 WILEY VCH. b Electro-mediated selective mono- and dicarboxylation of alkenes through the ENE pathway. Reproduced with permission from Ref. [60]. Copyright 2020 American Chemical Society

Fig. 6

Reproduced with permission from Ref. [63]. Copyright 2020 American Chemical Society

Fig. 7

Reproduced with permission from Ref. [64]. Copyright 2022 American Chemical Society

Fig. 8

Reproduced with permission from Ref. [65]. Copyright 2017 Royal Society of Chemistry

Fig. 9

Reproduced with permission from Ref. [21]. Copyright 2022 WILEY VCH

Fig. 10

Reproduced with permission from Ref. [68]. Copyright 2021 Asian Publication Corporation

Fig. 11

Reproduced with permission from Ref. [69]. Copyright 2021 American Chemical Society

Fig. 12

Reproduced with permission from Ref. [74]. Copyright 2019 American Chemical Society

Fig. 13

Reproduced with permission from Ref. [75]. Copyright 2021 Elsevier. b Perovskite oxide La0.7Sr0.3FeO3-catalyzed asymmetric electrochemical carboxylation. Reproduced with permission from Ref. [76]. Copyright 2021 Elsevier. c Asymmetric electrocarboxylation of aryl ketones with PrCoO3 as the cathode. Reproduced with permission from Ref. [18]. Copyright 2022 Royal Society of Chemistry

Fig. 14

Reproduced with permission from Ref. [77]. Copyright 2021 Wiley VCH

Fig. 15

Reproduced with permission from Ref. [78]. Copyright 2023 Springer Nature

Fig. 16

Reproduced with permission from Ref. [79]. Copyright 2021 Elsevier

Fig. 17

Reproduced with permission from Ref. [88]. Copyright 2021 Royal Society of Chemistry. b Electrocarboxylation of organic halides with Ag materials as the anode. Reproduced with permission from Ref. [84]. Copyright 2019 Royal Society of Chemistry

Fig. 18

Reproduced with permission from Ref. [89]. Copyright 2019 American Chemical Society. b Electro-induced carboxylation of organic bromides with CO2 through the EDEN pathway. Reproduced with permission from Ref. [92]. Copyright 2019 American Chemical Society

Fig. 19

Reproduced with permission from Ref. [95]. Copyright 2022 Wiley VCH

Fig. 20

Reproduced with permission from Ref. [16]. Copyright 2021 Springer Nature

Fig. 21

Reproduced with permission from Ref. [98]. Copyright 2020 Elsevier. b Electrosynthesis of ibuprofen via electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with CO2. Reproduced with permission from Ref. [80]. Copyright 2019 Royal Society of Chemistry

Fig. 22

Reproduced with permission from Ref. [99]. Copyright 2021 American Chemical Society. b Electrochemical desulfonylation carboxylation of organic sulfones with CO2 via EDEN mechanism. Reproduced with permission from Ref. [100]. Copyright 2021 American Chemical Society

Fig. 23

Reproduced with permission from Ref. [101]. Copyright 2019 WILEY VCH. b Electrocarboxylation of allyl esters with CO2 by cross-electrophile-coupling. Reproduced with permission from Ref. [102]. Copyright 2022 WILEY VCH

Fig. 24

Reproduced with permission from Ref. [104]. Copyright 2020 Royal Society of Chemistry

Fig. 25

Reproduced with permission from Ref. [105]. Copyright 2020 American Chemical Society

Fig. 26

Reproduced with permission from Ref. [106]. Copyright 2023 Royal Society of Chemistry

Fig. 27

Reproduced with permission from Ref. [108]. Copyright 2023 WILEY VCH

Fig. 28

Similar content being viewed by others

References

  1. Yan T, Liu H, Zeng ZX et al (2023) Recent progress of catalysts for synthesis of cyclic carbonates from CO2 and epoxides. J CO2 Util 68:102355

  2. Rehman A, Saleem F, Javed F et al (2021) Recent advances in the synthesis of cyclic carbonates via CO2 cycloaddition to epoxides. J Environ Chem Eng 9(2):105113

    Article  Google Scholar 

  3. Cai SF, Li HR, He LN (2021) Bifunctionalization of unsaturated bonds via carboxylative cyclization with CO2: a sustainable access to heterocyclic compounds. Green Chem 23(23):9334–9347

    Article  Google Scholar 

  4. Qiu CH, Bai S, Cao WJ et al (2020) Tunable syngas synthesis from photocatalytic CO2 reduction under visible-light irradiation by interfacial engineering. Trans Tianjin Univ 26(5):352–361

    Article  Google Scholar 

  5. Yang SY, Zhang L, Wang ZJ (2022) Advances in the preparation of light alkene from carbon dioxide by hydrogenation. Fuel 324:124503

    Article  Google Scholar 

  6. Ling YF, Ma QL, Yu YF et al (2021) Optimization strategies for selective CO2 electroreduction to fuels. Trans Tianjin Univ 27(3):180–200

    Article  Google Scholar 

  7. Biswal T, Shadangi KP, Sarangi PK et al (2022) Conversion of carbon dioxide to methanol: a comprehensive review. Chemosphere 298:134299

    Article  Google Scholar 

  8. Wang MY, Jin X, Wang XF et al (2021) Copper-catalyzed and proton-directed selective hydroxymethylation of alkynes with CO2. Angew Chem Int Ed 60(8):3984–3988

    Article  Google Scholar 

  9. Jin X, Fu HC, Wang MY et al (2021) Chemodivergent synthesis of one-carbon-extended alcohols via copper-catalyzed hydroxymethylation of alkynes with formic acid. Org Lett 23(13):4997–5001

    Article  Google Scholar 

  10. Chen XW, Zhu L, Gui YY et al (2019) Highly selective and catalytic generation of acyclic quaternary carbon stereocenters via functionalization of 1, 3-dienes with CO2. J Am Chem Soc 141(47):18825–18835

    Article  Google Scholar 

  11. Michigami K, Mita T, Sato Y (2017) Cobalt-catalyzed allylic C(sp3)–H carboxylation with CO2. J Am Chem Soc 139(17):6094–6097

    Article  Google Scholar 

  12. Li WD, Wu Y, Li SJ et al (2022) Boryl radical activation of benzylic C–OH bond: cross-electrophile coupling of free alcohols and CO2 via photoredox catalysis. J Am Chem Soc 144(19):8551–8559

    Article  Google Scholar 

  13. Amrillah T, Supandi AR, Puspasari V et al (2022) MXene-based photocatalysts and electrocatalysts for CO2 conversion to chemicals. Trans Tianjin Univ 28(4):307–322

    Article  Google Scholar 

  14. Li CH, Yuan GQ, Ji XC et al (2011) Highly regioselective electrochemical synthesis of dioic acids from dienes and carbon dioxide. Electrochim Acta 56(3):1529–1534

    Article  Google Scholar 

  15. Yang HP, Zhang HW, Wu Y et al (2018) A core–shell-structured silver nanowire/nitrogen-doped carbon catalyst for enhanced and multifunctional electrofixation of CO2. Chemsuschem 11(22):3905–3910

    Article  Google Scholar 

  16. Sun GQ, Zhang W, Liao LL et al (2021) Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2. Nat Commun 12(1):7086

    Article  Google Scholar 

  17. Chen BL, Tu ZY, Zhu HW et al (2014) CO2 as a C1-organic building block: enantioselective electrocarboxylation of aromatic ketones with CO2 catalyzed by cinchona alkaloids under mild conditions. Electrochim Acta 116:475–483

    Article  Google Scholar 

  18. Zhao YJ, Yang LR, Wang LT et al (2022) Asymmetric electrocarboxylation of 4’-methylacetophenone over PrCoO3 perovskites. Catal Sci Technol 12(9):2887–2893

    Article  Google Scholar 

  19. Seidler J, Roth A, Vieira L et al (2023) Electrochemical CO2 utilization for the synthesis of α-hydroxy acids. ACS Sustain Chem Eng 11(1):390–398

    Article  Google Scholar 

  20. Zhang K, Ren BH, Liu XF et al (2022) Direct and selective electrocarboxylation of styrene oxides with CO2 for accessing β-hydroxy acids. Angew Chem Int Ed 61(38):e202207660

    Article  Google Scholar 

  21. Wang YW, Tang SY, Yang GQ et al (2022) Electrocarboxylation of aryl epoxides with CO2 for the facile and selective synthesis of β-hydroxy acids. Angew Chem Int Ed 61(38):e202207746

    Article  Google Scholar 

  22. You Y, Kanna W, Takano H et al (2022) Electrochemical dearomative dicarboxylation of heterocycles with highly negative reduction potentials. J Am Chem Soc 144(8):3685–3695

    Article  Google Scholar 

  23. Wang SY, Feng T, Wang YW et al (2022) Recent advances in electrocarboxylation with CO2. Chem – Asian J 17(17):e202200543

  24. Murtaza A, Qamar MA, Saleem K et al (2022) Renewable electricity enables green routes to fine chemicals and pharmaceuticals. Chem Rec 22(5):e202100296

    Article  Google Scholar 

  25. Ran CK, Liao LL, Gao TY et al (2021) Recent progress and challenges in carboxylation with CO2. Curr Opin Green Sustain Chem 32:100525

    Article  Google Scholar 

  26. Cao Y, He X, Wang N et al (2018) Photochemical and electrochemical carbon dioxide utilization with organic compounds. Chin J Chem 36(7):644–659

    Article  Google Scholar 

  27. Senboku H, Katayama A (2017) Electrochemical carboxylation with carbon dioxide. Curr Opin Green Sustain Chem 3:50–54

    Article  Google Scholar 

  28. Yu ZQ, Shi M (2022) Recent advances in the electrochemically mediated chemical transformation of carbon dioxide. Chem Commun 58(98):13539–13555

    Article  Google Scholar 

  29. Pradhan S, Das S (2023) Recent advances on the carboxylations of C(sp3)–H bonds using CO2 as the carbon source. Synlett 34:1–16

    Google Scholar 

  30. Yang ZX, Lai LC, Chen JZ et al (2023) Stereoselective electrochemical carboxylation of α, β-unsaturated sulfones. Chin Chem Lett 34(6):107956

    Article  Google Scholar 

  31. Liu XF, Zhang K, Tao L et al (2022) Recent advances in electrochemical carboxylation reactions using carbon dioxide. Green Chem Eng 3(2):125–137

    Article  Google Scholar 

  32. Yang ZX, Yu Y, Lai LC et al (2021) Carbon dioxide cycle via electrocatalysis: electrochemical carboxylation of CO2 and decarboxylative functionalization of carboxylic acids. Green Synth Catal 2(1):19–26

    Article  Google Scholar 

  33. Senboku H (2021) Electrochemical fixation of carbon dioxide: synthesis of carboxylic acids. Chem Rec 21(9):2354–2374

    Article  Google Scholar 

  34. Medvedeva XV, Medvedev JJ, Klinkova A (2021) Translating tactics from direct CO2 electroreduction to electroorganic coupling reactions with CO2. Adv Energy Sustain Res 2(6):2100001

    Article  Google Scholar 

  35. Wang WH, Himeda Y, Muckerman JT et al (2015) CO2 hydrogenation to formate and methanol as an alternative to photo- and electrochemical CO2 reduction. Chem Rev 115(23):12936–12973

    Article  Google Scholar 

  36. Du J, Zhang P, Liu HZ (2021) Electrochemical reduction of carbon dioxide to ethanol: an approach to transforming greenhouse gas to fuel source. Chem – Asian J 16(6):588–603

  37. Hong JT, Li M, Zhang JN et al (2019) C−H bond carboxylation with carbon dioxide. Chemsuschem 12(1):6–39

    Article  Google Scholar 

  38. Jin S, Hao ZM, Zhang K et al (2021) Advances and challenges for the electrochemical reduction of CO2 to CO: from fundamentals to industrialization. Angew Chem Int Ed 60(38):20627–20648

    Article  Google Scholar 

  39. Zhou W, Cheng K, Kang JC et al (2019) New horizon in C1 chemistry: breaking the selectivity limitation in transformation of syngas and hydrogenation of CO2 into hydrocarbon chemicals and fuels. Chem Soc Rev 48(12):3193–3228

    Article  Google Scholar 

  40. Han JY, Long C, Zhang J et al (2020) A reconstructed porous copper surface promotes selectivity and efficiency toward C2 products by electrocatalytic CO2 reduction. Chem Sci 11(39):10698–10704

    Article  Google Scholar 

  41. Shi YR, Xia CG, Huang Y et al (2021) Electrochemical approaches to carbonylative coupling reactions. Chem – Asian J 16(19):2830–2841

  42. Rawat A, Dhakla S, Lama P et al (2022) Fixation of carbon dioxide to aryl/aromatic carboxylic acids. J CO2 Util 59:101939

  43. Lu YX, Zou YQ, Zhao WX et al (2020) Nanostructured electrocatalysts for electrochemical carboxylation with CO2. Nano Sel 1(2):135–151

    Article  Google Scholar 

  44. Jia SH, Ma XD, Sun XF et al (2022) Electrochemical transformation of CO2 to value-added chemicals and fuels. CCS Chem 4(10):3213–3229

    Article  Google Scholar 

  45. Zhong WF, Huang WH, Ruan SH et al (2023) Frontispiece: electrocatalytic reduction of CO2 coupled with organic conversion to selectively synthesize high-value chemicals. Chem Eur J 29(20):e202382062

    Article  Google Scholar 

  46. Batista GMF, de Castro PP (2023) Advances in the transition metal catalyzed carboxylation of aryl electrophiles: a field full of opportunities for the Brazilian chemical society. Rev Virtual Quim 15(2):334–351

    Article  Google Scholar 

  47. Matthessen R, Fransaer J, Binnemans K et al (2014) Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids. Beilstein J Org Chem 10:2484–2500

    Article  Google Scholar 

  48. Gao DF, Li WJ, Wang HY et al (2022) Heterogeneous catalysis for CO2 conversion into chemicals and fuels. Trans Tianjin Univ 28(4):245–264

    Article  Google Scholar 

  49. Senboku H, Fujimura Y, Kamekawa H et al (2000) Divergent electrochemical carboxylation of vinyl triflates: new electrochemical synthesis of phenyl-substituted α, β-unsaturated carboxylic acids and aliphatic β-keto carboxylic acids. Electrochim Acta 45(18):2995–3003

    Article  Google Scholar 

  50. Bazzi S, Le Duc G, Schulz E et al (2019) CO2 activation by electrogenerated divalent samarium for aryl halide carboxylation. Org Biomol Chem 17(37):8546–8550

    Article  Google Scholar 

  51. Concellón JM, Rodríguez-Solla H (2004) β-Elimination reactions by using samarium diiodide. Chem Soc Rev 33(9):599–609

    Article  Google Scholar 

  52. Brandukova NE, Vygodskii YS, Vinogradova SV (1994) The use of samarium diiodide in organic and polymer synthesis. Russ Chem Rev 63(4):345–355

    Article  Google Scholar 

  53. Bazzi S, Schulz E, Mellah M (2019) Electrogenerated Sm(II)-catalyzed CO2 activation for carboxylation of benzyl halides. Org Lett 21(24):10033–10037

    Article  Google Scholar 

  54. Tortajada A, Ninokata R, Martin R (2018) Ni-catalyzed site-selective dicarboxylation of 1, 3-dienes with CO2. J Am Chem Soc 140(6):2050–2053

    Article  Google Scholar 

  55. Filardo G, Gambino S, Silvestri G et al (1984) Electrocarboxylation of styrene through homogeneous redox catalysis. J Electroanal Chem Interfacial Electrochem 177(1–2):303–309

    Article  Google Scholar 

  56. Yuan GQ, Jiang HF, Lin C et al (2008) Efficient electrochemical synthesis of 2-arylsuccinic acids from CO2 and aryl-substituted alkenes with nickel as the cathode. Electrochim Acta 53(5):2170–2176

    Article  Google Scholar 

  57. Tyssee DA, Baizer MM (1974) Electrocarboxylation. I. mono- and dicarboxylation of activated olefins. J Org Chem 39(19):2819–2823

  58. Wang H, Lin MY, Fang HJ et al (2007) Electrochemical dicarboxylation of styrene: synthesis of 2-phenylsuccinic acid. Chin J Chem 25(7):913–916

    Article  Google Scholar 

  59. Kim Y, Do Park G, Balamurugan M et al (2020) Electrochemical β-selective hydrocarboxylation of styrene using CO2 and water. Adv Sci 7(3):1900137

    Article  Google Scholar 

  60. Alkayal A, Tabas V, Montanaro S et al (2020) Harnessing applied potential: selective β-hydrocarboxylation of substituted olefins. J Am Chem Soc 142(4):1780–1785

    Article  Google Scholar 

  61. Sheta AM, Mashaly MA, Said SB et al (2020) Selective α, δ-hydrocarboxylation of conjugated dienes utilizing CO2 and electrosynthesis. Chem Sci 11(34):9109–9114

    Article  Google Scholar 

  62. Sheta AM, Alkayal A, Mashaly MA et al (2021) Selective electrosynthetic hydrocarboxylation of α, β-unsaturated esters with carbon dioxide. Angew Chem Int Ed 60(40):21832–21837

    Article  Google Scholar 

  63. Zhang W, Lin S (2020) Electroreductive carbofunctionalization of alkenes with alkyl bromides via a radical-polar crossover mechanism. J Am Chem Soc 142(49):20661–20670

    Article  Google Scholar 

  64. Zhang K, Liu XF, Zhang WZ et al (2022) Electrocarboxylation of N-acylimines with carbon dioxide: access to substituted α-amino acids. Org Lett 24(19):3565–3569

    Article  Google Scholar 

  65. Qu Y, Tsuneishi C, Tateno H et al (2017) Green synthesis of α-amino acids by electrochemical carboxylation of imines in a flow microreactor. React Chem Eng 2(6):871–875

    Article  Google Scholar 

  66. Naito Y, Nakamura Y, Shida N et al (2021) Integrated flow synthesis of α-amino acids by in situ generation of aldimines and subsequent electrochemical carboxylation. J Org Chem 86(22):15953–15960

    Article  Google Scholar 

  67. Liao LL, Wang ZH, Cao KG et al (2022) Electrochemical ring-opening dicarboxylation of strained carbon–carbon single bonds with CO2: facile synthesis of diacids and derivatization into polyesters. J Am Chem Soc 144(5):2062–2068

    Article  Google Scholar 

  68. Singh K, Sohal HS, Singh B (2021) Synthesis of α-hydroxycarboxylic acids from various aldehydes and ketones by direct electrocarboxylation: a facile, efficient and atom economy protocol. Asian J Chem 33(4):839–845

    Article  Google Scholar 

  69. Stalcup MA, Nilles CK, Lee HJ et al (2021) Organic electrosynthesis in CO2-expanded electrolytes: enabling selective acetophenone carboxylation to atrolatic acid. ACS Sustainable Chem Eng 9(31):10431–10436

    Article  Google Scholar 

  70. Zhao SF, Wu LX, Wang H et al (2011) A unique proton coupled electron transfer pathway for electrochemical reduction of acetophenone in the ionic liquid [BMIM][BF4] under a carbon dioxide atmosphere. Green Chem 13(12):3461–3468

    Article  Google Scholar 

  71. Doherty AP, Marley E, Barhdadi R et al (2018) Mechanism and kinetics of electrocarboxylation of aromatic ketones in ionic liquid. J Electroanal Chem 819:469–473

    Article  Google Scholar 

  72. Endres F (2010) Physical chemistry of ionic liquids. Phys Chem Chem Phys 12(8):1648

    Article  Google Scholar 

  73. Zhao SF, Horne M, Bond AM et al (2014) Electrocarboxylation of acetophenone in ionic liquids: the influence of proton availability on product distribution. Green Chem 16(4):2242–2251

    Article  Google Scholar 

  74. Muchez L, De Vos DE, Kim M (2019) Sacrificial anode-free electrosynthesis of α-hydroxy acids via electrocatalytic coupling of carbon dioxide to aromatic alcohols. ACS Sustain Chem Eng 7(19):15860–15864

    Article  Google Scholar 

  75. Yang LR, Zhao YJ, Jiang CJ et al (2021) Perovskite La0.7Sr0.3Fe0.8B0.2O3 (B=Ti, Mn Co, Ni, and Cu) as heterogeneous electrocatalysts for asymmetric electrocarboxylation of aromatic ketones. J Catal 401:224–233

    Article  Google Scholar 

  76. Yang LR, Zhang JJ, Zhao YJ et al (2021) La1−xSrxFeO3 perovskite electrocatalysts for asymmetric electrocarboxylation of acetophenone with CO2. Electrochim Acta 398:139308

    Article  Google Scholar 

  77. Mena S, Louault C, Mesa V et al (2021) Electrochemical reduction of 4-nitrobenzyl phenyl thioether for activation and capture of CO2. ChemElectroChem 8(14):2649–2661

    Article  Google Scholar 

  78. Sun GQ, Yu P, Zhang W et al (2023) Electrochemical reactor dictates site selectivity in N-heteroarene carboxylations. Nature 615(7950):67–72

    Article  Google Scholar 

  79. Medvedev JJ, Medvedeva XV, Engelhardt H et al (2021) Relative activity of metal cathodes towards electroorganic coupling of CO2 with benzylic halides. Electrochim Acta 387:138528

    Article  Google Scholar 

  80. Mena S, Sanchez J, Guirado G (2019) Electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with a silver cathode in ionic liquids: an environmentally benign and efficient way to synthesize Ibuprofen. RSC Adv 9(26):15115–15123

    Article  Google Scholar 

  81. Mubarak MS, Peters DG (2017) Using silver cathodes for organic electrosynthesis and mechanistic studies. Curr Opin Electrochem 2(1):60–66

    Article  Google Scholar 

  82. Yang HP, Wu LX, Wang H et al (2016) Cathode made of compacted silver nanoparticles for electrocatalytic carboxylation of 1-phenethyl bromide with CO2. Chin J Catal 37(7):994–998

    Article  Google Scholar 

  83. Isse AA, Falciola L, Mussini PR et al (2006) Relevance of electron transfer mechanism in electrocatalysis: the reduction of organic halides at silver electrodes. Chem Commun 3:344–346

    Article  Google Scholar 

  84. Wu LX, Zhao YG, Guan YB et al (2019) Silver encapsulated copper salen complex: efficient catalyst for electrocarboxylation of cinnamyl chloride with CO2. RSC Adv 9(56):32628–32633

    Article  Google Scholar 

  85. Reche I, Mena S, Gallardo I et al (2019) Electrocarboxylation of halobenzonitriles: an environmentally friendly synthesis of phthalate derivatives. Electrochim Acta 320:134576

    Article  Google Scholar 

  86. Wang HM, Sui GJ, Wu D et al (2016) Selective electrocarboxylation of bromostyrene at silver cathode in DMF. Tetrahedron 72(7):968–972

    Article  Google Scholar 

  87. Isse AA, Gottardello S, Maccato C, et al (2006) Silver nanoparticles deposited on glassy carbon. Electrocatalytic activity for reduction of benzyl chloride. Electrochem Commun 8(11):1707–1712

  88. Shan SL, Jiang CJ, Liu YT et al (2021) Electrocatalytic carboxylation of halogenated compounds with mesoporous silver electrode materials. RSC Adv 11(36):21986–21990

    Article  Google Scholar 

  89. Medvedev JJ, Medvedeva XV, Li F et al (2019) Electrochemical CO2 fixation to α-methylbenzyl bromide in divided cells with nonsacrificial anodes and aqueous anolytes. ACS Sustain Chem Eng 7(24):19631–19639

    Article  Google Scholar 

  90. Senboku H, Nagakura K, Fukuhara T et al (2015) Three-component coupling reaction of benzylic halides, carbon dioxide, and N,N-dimethylformamide by using paired electrolysis: sacrificial anode-free efficient electrochemical carboxylation of benzylic halides. Tetrahedron 71(23):3850–3856

    Article  Google Scholar 

  91. Santiago S, Richart C, Mena S et al (2022) Electrocarboxylation of spiropyran switches through carbon-bromide bond cleavage reaction. ChemElectroChem 9(8):e202101559

    Article  Google Scholar 

  92. Yang DT, Zhu MH, Schiffer ZJ et al (2019) Direct electrochemical carboxylation of benzylic C–N bonds with carbon dioxide. ACS Catal 9(5):4699–4705

    Article  Google Scholar 

  93. Katayama A, Senboku H (2016) Sequential vinyl radical cyclization/fixation of carbon dioxide through electrochemical reduction of vinyl bromide in the presence of an electron-transfer mediator. ChemElectroChem 3(12):2052–2057

    Article  Google Scholar 

  94. Katayama A, Senboku H, Hara S (2016) Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in the presence of carbon dioxide. Tetrahedron 72(31):4626–4636

    Article  Google Scholar 

  95. Wang YW, Zhao ZW, Pan D et al (2022) Metal-free electrochemical carboxylation of organic halides in the presence of catalytic amounts of an organomediator. Angew Chem 134(41):e202210201

    Article  Google Scholar 

  96. Feng QJ, Huang KL, Liu SQ et al (2010) Electrocatalytic carboxylation of 2-amino-5-bromopyridine with CO2 in ionic liquid 1-butyl-3-methyllimidazoliumtetrafluoborate to 6-aminonicotinic acid. Electrochim Acta 55(20):5741–5745

    Article  Google Scholar 

  97. Tateno H, Nakabayashi K, Kashiwagi T et al (2015) Electrochemical fixation of CO2 to organohalides in room-temperature ionic liquids under supercritical CO2. Electrochim Acta 161:212–218

    Article  Google Scholar 

  98. Mena S, Santiago S, Gallardo I et al (2020) Sustainable and efficient electrosynthesis of naproxen using carbon dioxide and ionic liquids. Chemosphere 245:125557

    Article  Google Scholar 

  99. Senboku H, Minemura Y, Suzuki Y et al (2021) Synthesis of N-boc-α-amino acids from carbon dioxide by electrochemical carboxylation of N-boc-α-aminosulfones. J Org Chem 86(22):16077–16083

    Article  Google Scholar 

  100. Zhong JS, Yang ZX, Ding CL et al (2021) Desulfonylative electrocarboxylation with carbon dioxide. J Org Chem 86(22):16162–16170

    Article  Google Scholar 

  101. Senboku H, Sakai K, Fukui A et al (2019) Efficient synthesis of Mandel acetates by electrochemical carboxylation of benzal diacetates. ChemElectroChem 6(16):4158–4164

    Article  Google Scholar 

  102. Zhao R, Lin ZP, Maksso I et al (2022) Electrochemical cross-electrophile-coupling for transition-metal-free allylic carboxylation with ambient CO2. ChemElectroChem 9(21):e202200989

    Article  Google Scholar 

  103. Yan SS, Wu DS, Ye JH et al (2019) Copper-catalyzed carboxylation of C-F bonds with CO2. ACS Catal 9(8):6987–6992

    Article  Google Scholar 

  104. Gao XT, Zhang Z, Wang X et al (2020) Direct electrochemical defluorinative carboxylation of α-CF3 alkenes with carbon dioxide. Chem Sci 11(38):10414–10420

    Article  Google Scholar 

  105. Xie SL, Gao XT, Wu HH et al (2020) Direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with carbon dioxide. Org Lett 22(21):8424–8429

    Article  Google Scholar 

  106. Zhao B, Pan ZC, Pan JY et al (2023) Regiodivergent electroreductive defluorinative carboxylation of gem-difluorocyclopropanes. Green Chem 25(8):3095–3102

    Article  Google Scholar 

  107. Yuan GQ, Li LG, Jiang HF et al (2010) Electrocarboxylation of carbon dioxide with polycyclic aromatic hydrocarbons using Ni as the cathode. Chin J Chem 28(10):1983–1988

    Article  Google Scholar 

  108. Zhao ZW, Liu Y, Wang SY et al (2023) Site-selective electrochemical C−H carboxylation of arenes with CO2. Angew Chem Int Ed 62(3):e202214710

    Article  Google Scholar 

Download references

Acknowledgements

Financial support was received from the National Natural Science Foundation of China (No. 22278305) and National Key R&D Program of China (2022YFB4101900).

Author information

Authors and Affiliations

  1. School of Chemical Engineering and Technology, Key Laboratory for Green Chemical Technology of Ministry of Education, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin, 300072, China

    He Yao, Mei-Yan Wang, Chengguang Yue, Bangman Feng, Wenhao Ji, Chunbo Qian, Shengping Wang, Sheng Zhang & Xinbin Ma

  2. Ningbo Key Laboratory of Green Petrochemical Carbon Emission Reduction Technology and Equipment, Zhejiang Institute of Tianjin University, Ningbo, 315200, China

    Mei-Yan Wang & Sheng Zhang

Authors
  1. He Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mei-Yan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chengguang Yue
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Bangman Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wenhao Ji
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Chunbo Qian
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Shengping Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Sheng Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Xinbin Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mei-Yan Wang or Xinbin Ma.

Ethics declarations

Conflict of interest

Xinbin Ma is an editorial board member for Transactions of Tianjin University and was not involved in the editorial review or the decision to publish this article. All authors declare that there are no competing interests.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yao, H., Wang, MY., Yue, C. et al. Electrocarboxylation of CO2 with Organic Substrates: Toward Cathodic Reaction. Trans. Tianjin Univ. 29, 254–274 (2023). https://doi.org/10.1007/s12209-023-00361-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12209-023-00361-2

Keywords

Search

Navigation