Journal of East China Normal University(Natural Science) >

2023 , Vol. 2023 >Issue 1: 140 - 148

DOI: https://doi.org/10.3969/j.issn.1000-5641.2023.01.014

CO2 Utilization

Electrocatalytic coupling of CO2 with organic compounds to value-added chemicals

  • Huan WANG ,
  • Jiaxing LU
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  • 1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai　200062, China
    2. Institute of Eco-Chongming, Shanghai　202162, China

Received date: 2022-06-27

  Accepted date: 2022-09-09

  Online published: 2023-01-07

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Abstract

The efficient fixation and utilization of CO2 under mild conditions is one of the key components of green carbon science. The electrocatalytic coupling of CO2 and organic compounds can produce value-added chemicals, which is beneficial to sustainable development. In this review, we summarize the current methods of synthesizing carboxylic acids, organic carbonates, carbamates, and other chemicals via electrocatalytic CO2 coupling with organic compounds. We also present the latest research progress and opportunities in this field, such as asymmetric electrocarboxylation to construct chiral molecules, electrochemical ring-opening carboxylation, electrochemical N-methylation, electrocarboxylation with non-sacrificial anodes, and paired electrosynthesis.

Key words： carbon dioxide; electrocarboxylation; electrocatalysis; electroorganic synthesis

Cite this article

Huan WANG , Jiaxing LU . Electrocatalytic coupling of CO2 with organic compounds to value-added chemicals[J]. Journal of East China Normal University(Natural Science), 2023 , 2023(1) : 140 -148 . DOI: 10.3969/j.issn.1000-5641.2023.01.014

References

1 HE M Y, SUN Y H, HAN B X. Green carbon science: Efficient carbon resource processing, utilization, and recycling towards carbon neutrality. Angewandte Chemie-International Edition, 2022, 61 (15): e202112835.
2 LIANG H Q, BEWERIES T, FRANCKE R, et al. Molecular catalysts for the reductive homocoupling of CO2 towards C2+ compounds . Angewandte Chemie-International Edition, 2022, 61 (19): e202200723.
3 XU S Z, CARTER E A. Theoretical insights into heterogeneous (photo)electrochemical CO2 reduction . Chemical Reviews, 2019, 119, 6631- 6669.
4 LEE S, KIM D, LEE J. Electrocatalytic oroduction of C3-C4 compounds by conversion of CO2 on a chloride-induced Bi-phasic Cu2O-Cucatalyst . Angewandte Chemie-International Edition, 2015, 54 (49): 14701- 14705.
5 ANG N W J, OLIVEIRA J C A, ACKERMANN L. Electroreductive cobalt-catalyzed carboxylation: Cross-electrophile electrocoupling with atmospheric CO2. Angewandte Chemie-International Edition, 2020, 59 (31): 12842- 12847.
6 LAN Y C, WANG H, WU L X, et al. Electroreduction of dibromobenzenes on silver electrode in the presence of CO2. Journal of Electroanalytical Chemistry, 2012, 664, 33- 38.
7 MENA S, SANTIAGO S, GALLARDO I, et al. Sustainable and efficient electrosynthesis of naproxen using carbon dioxide and ionic liquids. Chemosphere, 2020, 245, 125557.
8 YANG H P, WU L X, WANG H, et al. Cathode made of compacted silver nanoparticles for electrocatalytic carboxylation of 1-phenethyl bromide with CO2. Chinese Journal of Catalysis, 2016, 37, 994- 998.
9 YANG D T, ZHU M H, SCHIFFER Z J, et al. Direct electrochemical carboxylation of benzylic C–N bonds with carbon dioxide. ACS Catalysis, 2019, 9 (5): 4699- 4705.
10 SENBOKU H, SAKAI K, FUKUI A, et al. Efficient synthesis of mandel acetates by electrochemical carboxylation of benzal diacetates. ChemElectroChem, 2019, 6 (16): 4158- 4164.
11 ZHONG J S, YANG Z X, DING C L, et al. Desulfonylative electrocarboxylation with carbon dioxide. The Journal of Organic Chemistry, 2021, 86, 16162- 16170.
12 QUAN Y L, YU R H, ZHU J X, et al. Efficient carboxylation of styrene and carbon dioxide by single-atomic copper electrocatalyst. Journal of Colloid and Interface Science, 2021, 601, 378- 384.
13 ALKAYAL A, TABAS V, MONTANARO S, et al. Harnessing applied potential: Delective β-hydrocarboxylation of substituted olefins. Journal of the American Chemical Society, 2020, 142, 1780- 1785.
14 KIM Y, PARK G D, BALAMURUGAN M, et al. Electrochemical β-selective hydrocarboxylation of styrene using CO2 and water . Advanced Science, 2020, 7 (3): 1900137.
15 GHOBADI K, ZARE H R, KHOSHRO H, et al. Electrosynthesis of cinnamic acid by electrocatalytic carboxylation of phenylacetylene in the presence of [NiⅡ(Me4-NO2Bzo[15]tetraeneN4)] complex: An EC′ CCC′ C mechanism. Comptes Rendus Chimie, 2018, 21, 14- 18.
16 LI C H, YUAN G Q, JIANG H F. Electrocarboxylation of alkynes with carbon dioxide in the presence of metal salt catalysts. Chinese Journal of Chemistry, 2010, 28, 1685- 1689.
17 STALCUP M A, NILLES C K, LEE H J, et al. Organic electrosynthesis in CO2-eXpanded electrolytes: Enabling selective acetophenone carboxylation to atrolatic acid . ACS Sustainable Chemistry & Engineering, 2021, 9 (31): 10431- 10436.
18 SENBOKU H, YAMAUCHI Y, FUKUHARA T, et al. Electrochemical carboxylation of aliphatic ketones: Synthesis of beta-keto carboxylic acids. Electrochemistry, 2006, 74, 612- 614.
19 WANG H, ZHU H W, GUO R R, et al. Computational and experimental study on electrocarboxylation of benzalacetone. Asian Journal of Organic Chemistry, 2017, 6 (10): 1380- 1384.
20 QU Y, TSUNEISHI C, TATENO H, et al. Green synthesis of α-amino acids by electrochemical carboxylation of imines in a flow microreactor. Reaction Chemistry & Engineering, 2017, 2 (6): 871- 875.
21 WU L X, YANG H P, GUAN Y B, et al. Electrosynthesis of cyclic carbonates from CO2 and epoxides on compacted silver nanoparticles electrode . International Journal of Electrochemical Science, 2017, 12 (10): 8963- 8972.
22 WANG H, WU L X, ZHAO J Q, et al. Synthesis of cyclic carbonates from CO2 and diols via electrogenerated cyanomethyl anion . Greenhous Gases-Science and Technology, 2012, 2 (1): 59- 65.
23 LEE K M, JANG J H, BALAMURUGAN M, et al. Redox-neutral electrochemical conversion of CO2 to dimethyl carbonate . Nature Energy, 2021, 6, 733- 741.
24 FORTE G, CHIAROTTO I, RICHTER F, et al. Towards a sustainable electrochemical activation for recycling CO2: Synthesis of bis-O-alkylcarbamates from aliphatic and benzyl diamines . Reaction Chemistry & Engineering, 2017, 2 (5): 646- 649.
25 TASCEDDA P, DUNACH E. Electrosynthesis of cyclic carbamates from aziridines and carbon dioxide [J]. Chemical Communications, 2000(6): 449-450.
26 ORSINI M, FEROCI M, SOTGIU G, et al. Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives. Organic & Biomolecular Chemistry, 2005, 3 (7): 1202- 1208.
27 FEROCI M, INESI A, ORSINI M, et al. Electrochemical carboxylation of N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one: An efficient route to unsymmetrical methylmalonic ester derivatives. Organic Letters, 2002, 4 (16): 2617- 2620.
28 CHEN B L, TU Z Y, ZHU H W, et al. CO2 as a C1-organic building block: Enantioselective electrocarboxylation of aromatic ketones with CO2 catalyzed by cinchona alkaloids under mild conditions . Electrochimica Acta, 2014, 116, 475- 483.
29 CHEN B L, ZHU H W, XIAO Y, et al. Asymmetric electrocarboxylation of 1-phenylethyl chloride catalyzed by electrogenerated chiral [COI(salen)]- complex. Electrochemistry Communications, 2014, 42, 55- 59.
30 JIAO K J, LI Z M, XU X T, et al. Palladium-catalyzed reductive electrocarboxylation of allyl esters with carbon dioxide. Organic Chemistry Frontiers, 2018, 5 (14): 2244- 2248.
31 YANG H P, YUE Y N, SUN Q L, et al. Entrapment of a chiral cobalt complex within silver: A novel heterogeneous catalyst for asymmetric carboxylation of benzyl bromides with CO2. Chemical Communications, 2015, 51, 12216- 12219.
32 YANG H P, CHI D H, SUN Q L, et al. Entrapment of alkaloids within silver: From enantioselective hydrogenation to chiral recognition. Chemical Communications, 2014, 50, 8868- 8870.
33 YANG H P, FEN Q, WANG H, et al. Copper encapsulated alkaloids composite: An effective heterogeneous catalyst for electrocatalytic asymmetric hydrogenation. Electrochemistry Communications, 2016, 71, 38- 42.
34 YANG L R, ZHANG J J, ZHAO Y J, et al. La1?xSrxFeO3perovskite electrocatalysts for asymmetric electrocarboxylation of acetophenone with CO2. Electrochimica Acta, 2021, 398, 139308.
35 YANG L R, ZHAO Y J, JIANG C J, et al. Perovskite La0.7Sr0.3Fe0.8B0.2O3 (B = Ti, Mn, Co, Ni, and Cu) as heterogeneous electrocatalysts for asymmetric electrocarboxylation of aromatic ketones . Jouranl Catalysis, 2021, 401, 224- 233.
36 ZHAO Y J, YANG L R, WANG L T, et al. Asymmetric electrocarboxylation of 4′ -methylacetophenone over PrCoO3 perovskites . Catalysis Science & Technology, 2022, 12 (9): 2887- 2893.
37 LIAO L L, WANG Z H, CAO K G, et al. Electrochemical ring-opening dicarboxylation of strained carbon–carbon single bonds with CO2: Facile synthesis of diacids and derivatization into polyesters . Journal of the American Chemical Society, 2022, 144, 2062- 2068.
38 SUN X F, ZHU Q G, HU J Y, et al. N,N-Dimethylation of nitrobenzenes with CO2 and water by electrocatalysis . Chemical Science, 2017, 8 (8): 5669- 5674.
39 ROONEY C L, WU Y S, TAO Z X, et al. Electrochemical eeductive N-methylation with CO2 enabled by a molecular catalyst . Journal of the American Chemical Society, 2021, 143, 19983- 19991.
40 SENBOKU H, NAGAKURA K, FUKUHARA T, et al. 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, 2015, 71, 3850- 3856.
41 GRINBERG V A, KOCH T A, MAZIN V M, et al. Electrocarboxylation of 1,4-dibromobut-2-ene in a CO2-DMF liquid mixture . Russian Chemical Bulletin, 1997, 46, 1560- 1564.
42 CORBIN N, YANG D T, LAZOUSKI N, et al. Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes. Chemical Science, 2021, (12): 12365- 12376.
43 MEDVEDEV J J, MEDVEDEVA X V, LI F, et al. Electrochemical CO2 fixation to α-methylbenzyl bromide in divided cells with nonsacrificial anodes and aqueous anolytes . ACS Sustainable Chemistry & Engineering, 2019, 7 (24): 19631- 19639.
44 SHETA A M, MASHALY M A, SAID S B, et al. Selective α,δ-hydrocarboxylation of conjugated dienes utilizing CO2 and electrosynthesis . Chemical Science, 2020, 11 (34): 9109- 9114.
45 MATTHESSEN R, FRANSAER J, BINNEMANS K, et al. Paired electrosynthesis of diacid and diol precursors using dienes and CO2 as the carbon source . ChemElectroChem, 2015, 2 (1): 73- 76.
46 MUCHEZ L, DE VOS D E, KIM M J. Sacrificial anode-free electrosynthesis of α-hydroxy acids via electrocatalytic coupling of carbon dioxide to aromatic alcohols. ACS Sustainable Chemistry & Engineering, 2019, 7 (19): 15860- 15864.
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