CO₂/NO_x-involved Electrochemical C-N Coupling Reactions

Abstract

With the excessive use of fossil fuels leading to significant CO₂ emissions, and the continuous increase of NO_x in water bodies and soils, the use of electrochemical methods for the conversion of CO₂ and NO_x has garnered widespread attention as a green chemical approach due to its advantages of being environmentally friendly, low-carbon, and straightforward. C—N bonds are widely present in many value-added chemicals, such as urea, amides, and oximes. However, traditional methods for constructing C—N bonds typically involve thermochemical processes. Therefore, using electrochemical methods to catalyze the reduction of CO₂ and NO_x for C—N bond formation has emerged as a green and sustainable alternative. This paper summarizes the research progress of electrochemical C—N bond construction involving CO₂ and NO_x from the perspectives of reaction mechanisms and catalytic system construction, reviews the electrochemical synthesis of urea, amines, amides, and oximes through electrochemical C—N bond construction, and finally analyzes the current problems and challenges in the field, providing prospects for its future development.

Keywords

CO₂ reduction / NO_x reduction / C-N coupling / Electrocatalysis

References

[1] Daw R, Finkelstein J, Helmer M. Nature. 2012, 488: 293

[2] Ross M B, de Luna P, Li Y F, Dinh C T, Kim D, Yang P D, Sargent E H. Nat. Catal.. 2019, 2: 648

[3] Chu S, Majumdar A. Nature. 2012, 48: 294

[4] Bogdanov D, Ram M, Aghahosseini A, Gulagi A, Oyewo A S, Child M, Caldera U, Sadovskaia K, Farfan J, de Souza Noel Simas Barbosa L, Fasihi M, Khalili S, Traber T, Breyer C. Energy. 2021, 227: 120467

[5] Tao Z X, Wu Z S, Wu Y S, Wang H L. ACS Catal.. 2020, 10: 9271

[6] Xie M S, Xia B Y, Li Y, Yan Y, Yang Y, Sun Q, Chan S H, Fisher A, Wang X. Energy Environ. Sci.. 2016, 9: 1687

[7] Sun X F, Chen C J, Liu S J, Hong S, Zhu Q G, Qian Q L, Han B X, Zhang J, Zheng L R. Angew. Chem. Int. Ed.. 2019, 58: 4669

[8] Zhang L B, Feng J Q, Liu S J, Tan X X, Wu L M, Jia S H, Xu L, Ma X D, Song X N, Ma J, Sun X F, Han B X. Adv. Mater.. 2023, 35: 2209590

[9] Wu Y S, Yuan X S, Tao Z S, Wang H S. Chem. Commun.. 2019, 55: 8864

[10] Li F W, Li Y C, Wang Z Y, Li J, Nam D H, Lum Y W, Luo M C, Wang X, Ozden A, Hung S F, Chen B, Wang Y H, Wicks J, Xu Y, Li Y L, Gabardo C M, Dinh C T, Wang Y, Zhuang T T, Sinton D, Sargent E H. Nat. Catal.. 2020, 3: 75

[11] Guo W W, Liu S J, Tan X X, Wu R Z, Yan X P, Chen C J, Zhu Q G, Zheng L R, Ma J Y, Zhang J, Huang Y Y, Sun X F, Han B X. Angew. Chem. Int. Ed.. 2021, 60: 21979

[12] Huo S J, Weng Z, Wu Z S, Zhong Y R, Wu Y S, Fang J H, Wang H L. ACS Appl. Mater. Interfaces. 2017, 9: 28519

[13] Feng J Q, Wu L M, Liu S J, Xu L, Song X N, Zhang L B, Zhu Q G, Kang X C, Sun X F, Han B X. J. Am. Chem. Soc.. 2023, 145: 9857

[14] Wu Y S, Jiang Z, Lu X, Liang Y Y, Wang H L. Nature. 2019, 575: 639

[15] Wu Y S, Jiang J B, Weng Z, Wang M Y, Broere D L J, Zhong Y R, Brudvig G W, Feng Z X, Wang H L. ACS Cent. Sci.. 2017, 3: 847

[16] Zhang L B, Feng J Q, Wu L M, Ma X D, Song X N, Jia S H, Tan X X, Jin X Y, Zhu Q G, Kang X C, Ma J, Qian Q L, Zheng L R, Sun X F, Han B X. J. Am. Chem. Soc.. 2023, 145: 21945

[17] Wei X, Yin Z S, Lyu K J, Li Z, Gong J, Wang G W, Xiao L, Lu J, Zhuang L. ACS Catal.. 2020, 10: 4103

[18] Guo W W, Tan X X, Bi J H, Xu L, Yang D X, Chen C J, Zhu Q G, Ma J, Tayal A, Ma J Y, Huang Y Y, Sun X F, Liu S J, Han B X. J. Am. Chem. Soc.. 2021, 143: 6877

[19] Zhou Y, Zhou R, Zhu X R, Han N, Song B, Liu T C, Hu G Z, Li Y F, Lu J, Li Y G. Adv. Mater.. 2020, 32: 2000992

[20] Cai Z, Wu Y S, Wu Z S, Yin L C, Weng Z, Zhong Y R, Xu W W, Sun X M, Wang H L. ACS Energy Lett.. 2018, 3: 2816

[21] Hursán D, Timoshenko J, Ortega E, Jeon H S, Rüscher M, Herzog A, Rettenmaier C, Chee S W, Martini A, Koshy D, Roldán Cuenya B. Adv. Mater.. 2023, 36: 2307809

[22] Xu L, Ma X D, Wu L M, Tan X X, Song X N, Zhu Q G, Chen C J, Qian Q L, Liu Z M, Sun X F, Liu S J, Han B X. Angew. Chem. Int. Ed.. 2022, 61: e202210375

[23] Tao Z X, Rooney C L, Liang Y Y, Wang H L. J. Am. Chem. Soc.. 2021, 143: 19630

[24] Wei X X, Chen C, Fu X Z, Wang S Y. Adv. Energy Mater.. 2023, 14: 2303027

[25] Chen C J, Sun X F, Yan X P, Wu Y H, Liu H Z, Zhu Q G, Bediako B B A, Han B X. Angew. Chem. Int. Ed.. 2020, 59: 11123

[26] Wang X Y, Zhao Z W, Zahra K, Li J J, Zhang Z C. Chem. Res. Chinese Universities. 2023, 39: 580

[27] Zhao X G, Wang Y L. Chem. J. Chinese Universities. 2024, 45: 20230527

[28] Kong Y, Wei W. Acta Phys.-Chim. Sin.. 2023, 40: 2307049

[29] Yao H, Wang M Y, Yue C G, Feng B M, Ji W H, Qian C B, Wang S P, Zhang S, Ma X B. Trans. Tianjin Univ.. 2023, 29: 254

[30] Xu L, Tan X Y, He Z H, Hao L D, Wang W T, Liu Z T, Robertson A W, Sun Z Y. Matter. 2024, 7: 59

[31] Guo W J, Li G F, Bai C B, Liu Q, Chen F X, Chen R. Nat. Commun.. 2024, 15: 1573

[32] Li X, Chen Y X, Zhan X Y, Xu Y W, Hao L D, Xu L, Li X Y, Umer M, Tan X Y, Han B X, Robertson A W, Sun Z Y. The Innov. Mater.. 2023, 1: 100014

[33] van Langevelde P H, Katsounaros I, Koper M T M. Joule. 2021, 5: 290

[34] Gao W S, Xie K F, Xie J, Wang X M, Zhang H, Chen S Q, Wang H, Li Z L, Li C. Adv. Mater.. 2023, 35: 2202952

[35] Wu ZY, Karamad M, Yong X, Huang Q Z, Cullen D A, Zhu P, Xia C, Xiao Q F, Shakouri M, Chen F Y, Kim J Y, Xia Y, Heck K, Hu Y, Wong M S, Li Q, Gates I, Siahrostami S, Wang H T. Nat. Commun.. 2021, 12: 2870

[36] Singh A R, Rohr B A, Schwalbe J A, Cargnello M, Chan K, Jaramillo T F, Chorkendorff I, Nørskov J K. ACS Catal.. 2017, 7: 706

[37] Gao Q, Yao B Q, Pillai H S, Zang W J, Han X, Liu Y Q, Yu S W, Yan Z H, Min B, Zhang S, Zhou H, Ma L, Xin H L, He Q, Zhu H Y. Nat. Synth.. 2023, 2: 624

[38] Li P P, Li R, Liu Y T, Xie M H, Jin Z Y, Yu G H. J. Am. Chem. Soc.. 2023, 145: 6471

[39] Xu Z, Wan L, Liao Y W, Pang M B, Xu Q, Wang P C, Wang B G. Nat. Commun.. 2023, 14: 1619

[40] Wu L M, Feng J Q, Zhang L B, Jia S H, Song X N, Zhu Q G, Kang X C, Xing X Q, Sun X F, Han B X. Angew. Chem. Int. Ed.. 2023, 62: e202307952

[41] Wu L M, Zhang L B, Liu S J, Feng J Q, Xu L, Tan X X, Ma X D, Sun X F. J. Mater. Chem. A. 2023, 11: 5520

[42] Jiang H F, Chen G F, Wang H H. Sci. China Chem.. 2024, 67: 319

[43] Jia S H, Wu L M, Tan X X, Feng J Q, Ma X D, Zhang L B, Song X N, Xu L, Zhu Q G, Kang X C, Sun X F, Han B X. J. Am. Chem. Soc.. 2024, 146: 10934

[44] Zhang B C, Dai Z C, Chen Y X, Cheng M Y, Zhang H K, Feng P Y, Ke B Q, Zhang Y Y, Zhang G Q. Nat. Commun.. 2024, 15: 2816

[45] Wu L. M., Jia S. H., Zhang L. B., Wang R. H., Feng J. Q., Sun X. F., Han B. X., Sci. China Chem., 2024, doi:https://doi.org/10.1007/s11426-024-2040-8.

[46] Liu K, Li H M, Xie M H, Wang P F, Jin Z Y, Liu Y T, Zhou M, Li P P, Yu G H. J. Am. Chem. Soc.. 2024, 146: 7779

[47] Roose P, Eller K, Henkes E, Rossbacher R, Höke H. Ullmann’s Encyclopedia of Industrial Chemistry. 2015, Berlin, John Wiley & Sons, Ltd.

[48] Meessen J H. Ullmann’s Encyclopedia of Industrial Chemistry. 2010, Berlin, John Wiley & Sons, Ltd.

[49] Appl M. Ullmann’s Encyclopedia of Industrial Chemistry. 2011, Berlin, John Wiley & Sons, Ltd.

[50] Zhang H T, Sun Z X, Hu Y H. Renew. Sust. Energ. Rev.. 2021, 149: 111330

[51] Li J, Zhang Y, Liu C, Zheng L R, Petit E, Qi K, Zhang Y, Wu H L, Wang W W, Tiberj A, Wang X C, Chhowalla M, Lajaunie L, Yu R H, Voiry D. Adv. Funct. Mater.. 2022, 32: 2108316

[52] Feng J Q, Zhang L B, Liu S J, Xu L, Ma X D, Tan X X, Wu L M, Qian Q L, Wu T B, Zhang J L, Sun X F, Han B X. Nat. Commun.. 2023, 14: 4615

[53] Li J N, Zhang Y X, Kuruvinashetti K, Kornienko N. Nat. Rev. Chem.. 2022, 6: 303

[54] Peng X Y, Zeng L B, Wang D S, Liu Z B, Li Y, Li Z J, Yang B, Lei L C, Dai L M, Hou Y. Chem. Soc. Rev.. 2023, 52: 2193

[55] Tan X X, Jia S H, Song X N, Ma X D, Feng J Q, Zhang L B, Wu L M, Du J, Chen A B, Zhu Q G, Sun X F, Han B X. Chem. Sci.. 2023, 14: 8214

[56] Liao P S, Kang J W, Xiang R N, Wang S H, Li G Q. Angew. Chem. Int. Ed.. 2023, 63: e202311752

[57] Li S. K., Zou Y. Q., Chen C., Wang S. Y., Liu Z.Q., Chin. Chem. Lett., 2023, 109147.

[58] Jia S H, Wu L M, Liu H L, Wang R H, Sun X F, Han B X. Angew. Chem. Int. Ed.. 2024, 136: e202400033

[59] Jiang M H, Wang H Z, Zhu M F, Luo X J, He Y, Wang M J, Wu C J, Zhang L Y, Li X, Liao X M, Jiang Z J, Jin Z. Chem. Soc. Rev.. 2024, 53: 5149

[60] Hu Q, Zhou W L, Qi S, Huo Q H, Li X, Lv M Y, Chen X B, Feng C, Yu J Y, Chai X Y, Yang H P, He C X. Nat. Sustain.. 2024, 7: 442

[61] Meng N N, Huang Y M, Liu Y, Yu Y F, Zhang B. Cell Rep. Phys. Sci.. 2021, 2: 100378

[62] Shibata M, Yoshida K, Furuya N. Denki Kagaku Oyobi Kogyo Butsuri Kagaku. 1998, 66: 584

[63] Shibata M, Yoshida K, Furuya N. J. Electroanal. Chem.. 1998, 442: 67

[64] Shibata M, Furuya N. J. Electroanal. Chem.. 2001, 507: 177

[65] Shibata M, Yoshida K, Furuya N. J. Electrochem. Soc.. 1998, 145: 595

[66] Shibata M, Yoshida K, Furuya N. J. Electroanal. Chem.. 1995, 387: 143

[67] Feng Y G, Yang H, Zhang Y, Huang X Q, Li L G, Cheng T, Shao Q. Nano Lett.. 2020, 20: 8282

[68] Yuan M L, Chen J W, Bai Y L, Liu Z J, Zhang J X, Zhao T K, Wang Q, Li S W, He H Y, Zhang G J. Angew. Chem. Int. Ed.. 2021, 60: 10910

[69] Sun X F, Zhu Q G, Hu J Y, Kang X C, Ma J, Liu H Z, Han B X. Chem. Sci.. 2017, 8: 5669

[70] Rooney C L, Wu Y S, Tao Z X, Wang H L. J. Am. Chem. Soc.. 2021, 143: 19983

[71] Wu Y S, Jiang Z, Lin Z C, Liang Y Y, Wang H L. Nat. Sustain.. 2021, 4: 725

[72] Wang J, Wu D J, Li M H, Wei X B, Yang X M, Shao M H, Gu M. Nano Lett.. 2022, 22: 5600

[73] Du H T, Guo H R, Wang K K, Du X N, Beshiwork B A, Sun S J, Luo Y S, Liu Q, Li T S, Sun X P. Angew. Chem. Int. Ed.. 2023, 62: e202215782

[74] Yao Y C, Zhao L, Dai J, Wang J X, Fang C Y, Zhan G M, Zheng Q, Hou W, Zhang L Z. Angew. Chem. Int. Ed.. 2022, 61: e202208215

[75] He W H, Zhang J, Dieckhöfer S, Varhade S, Brix A C, Lielpetere A, Seisel S, Junqueira J R C, Schuhmann W. Nat. Commun.. 2022, 13: 1129

[76] Lv C D, Zhong L X, Liu H J, Fang Z W, Yan C S, Chen M X, Kong Y, Lee C, Liu D B, Li S Z, Liu J W, Song L, Chen G, Yan Q Y, Yu G H. Nat. Sustain.. 2021, 4: 868

[77] Wu Y D, Chen W, Jiang Y M, Xu Y Z, Zhou B, Xu L T, Xie C, Yang M, Qiu M Y, Wang D D, Liu Q, Liu Q H, Wang S Y, Zou Y Q. Angew. Chem. Int. Ed.. 2023, 62: e202305491

[78] Guo C Y, Zhou W, Lan X E, Wang Y T, Li T L, Han S H, Yu Y F, Zhang B. J. Am. Chem. Soc.. 2022, 144: 16006

[79] Li J N, Kornienko N. Chem. Sci.. 2022, 13: 3957

[80] Zhang X R, Zhu X R, Bo S W, Chen C, Cheng K, Zheng J Y, Li S, Tu X J, Chen W, Xie C, Wei X X, Wang D D, Liu Y Y, Chen P S, Jiang S P, Li Y F, Liu Q H, Li C G, Wang S Y. Angew. Chem. Int. Ed.. 2023, 62: e202305447

[81] Wei X X, Wen X J, Liu Y Y, Chen C, Xie C, Wang D D, Qiu M Y, He N H, Zhou P, Chen W, Cheng J, Lin H Z, Jia J F, Fu X Z, Wang S Y. J. Am. Chem. Soc.. 2022, 144: 11530

[82] Xu M Q, Wu F F, Zhang Y, Yao Y H, Zhu G P, Li X Y, Chen L, Jia G, Wu X H, Huang Y J, Gao P, Ye W. Nat. Commun.. 2023, 14: 6994

[83] Luo Y T, Xie K, Ou P F, Lavallais C, Peng T, Chen Z, Zhang Z Y, Wang N, Li X Y, Grigioni I, Liu B L, Sinton D, Dunn J B, Sargent E H. Nat. Catal.. 2023, 6: 939

[84] Lan J, Wei Z X, Lu Y R, Chen D C, Zhao S L, Chan T S, Tan Y W. Nat. Commun.. 2023, 14: 2870

[85] Nam D H, De Luna P, Rosas-Hernández A, Thevenon A, Li F W, Agapie T, Peters J C, Shekhah O, Eddaoudi M, Sargent E H. Nat. Mater.. 2020, 19: 266

[86] Kim C, Bui J C, Luo X Y, Cooper J K, Kusoglu A, Weber A Z, Bell A T. Nat. Energy. 2021, 6: 1026

[87] König M, Vaes J, Klemm E, Pant D. iScience. 2019, 19: 135

[88] Wang H, Wu Y Y. Acta Phys.-Chim. Sin.. 2020, 37: 2010022

[89] Tan X X, Sun X F, Han B X. Natl. Sci. Rev.. 2022, 9: nwab022

[90] Gao D F, Wei P F, Li H F, Lin L, Wang G X, Bao X H. Acta Phys.-Chim. Sin.. 2021, 37: 2009021

[91] Pătru A, Binninger T, Pribyl B, Schmidt T J. J. Electrochem. Soc.. 2019, 166: F34

[92] Li Y C, Zhou D K, Yan Z F, Gonçalves R H, Salvatore D A, Berlinguette C P, Mallouk T E. ACS Energy Lett.. 2016, 1: 1149

[93] Wu T W, Zhu X J, Xing Z, Mou S Y, Li C B, Qiao Y X, Liu Q, Luo Y L, Shi X F, Zhang Y N, Sun X P. Angew. Chem.. 2019, 131: 18620

[94] Li Q L, Fang C, Yang Z H, Yu B, Takabatake M, Motokura K, Sun X Y, Yang Y. Small. 2022, 18: 2201343

[95] Chen C, Zhu X R, Wen X J, Zhou Y Y, Zhou L, Li H, Tao L, Li Q L, Du S Q, Liu T T, Yan D F, Xie C, Zou Y Q, Wang Y Y, Chen R, Huo J, Li Y F, Cheng J, Su H, Zhao X, Cheng W R, Liu Q H, Lin H Z, Luo J, Chen J, Dong M D, Cheng K, Li C G, Wang S Y. Nat. Chem.. 2020, 12: 717

[96] Yuan M L, Chen J W, Bai Y L, Liu Z J, Zhang J X, Zhao T K, Shi Q N, Li S W, Wang X, Zhang G J. Chem. Sci.. 2021, 12: 6048

[97] Yuan M L, Chen J W, Zhang H H, Li Q G, Zhou L, Yang C, Liu R J, Liu Z J, Zhang S J, Zhang G J. Energy Environ. Sci.. 2022, 15: 2084

[98] Li S M, Shi Y, Zhang J J, Wang Y, Wang H, Lu J X. ChemSusChem. 2021, 14: 2050

[99] Paul S, Sarkar S, Adalder A, Banerjee A, Ghorai U K. J. Mater. Chem. A. 2023, 11: 13249

[100] Zhao Y L, Ding Y X, Li W L, Liu C, Li Y Z, Zhao Z Q, Shan Y, Li F, Sun L C, Li F S. Nat. Commun.. 2023, 14: 4491

[101] Xiong T K, Zhou X Q, Zhang M, Tang H T, Pan Y M, Liang Y. Green Chem.. 2021, 23: 4328

[102] Wu Y M, Zhao J H, Wang C H, Li T L, Zhao B H, Song Z Y, Liu C B, Zhang B. Nat. Commun.. 2023, 14: 3057

[103] Tao Z X, Wu Y S, Wu Z S, Shang B, Rooney C, Wang H L. J. Energy Chem.. 2021, 65: 367

[104] He M, Wu Y M, Li R, Wang Y T, Liu C B, Zhang B. Nat. Commun.. 2023, 14: 5088

[105] Jouny M, Lv J J, Cheng T, Ko B H, Zhu J J, Goddard W A, Jiao F. Nat. Chem.. 2019, 11: 846