J.J. Medvedev, X.V. Medvedeva, H. Engelhardt et al.
Electrochimica Acta 387 (2021) 138528
Acknowledgments
[20] G.Q. Yuan, H.F. Jiang, C. Lin, S.J. Liao, Efficient electrochemical synthesis of 2-
This work was supported by the Russian Science Foundation
[Project No. 20-73-10165]. J.J.M., X.V.M. and A.K. acknowledge the
financial support from the University of Waterloo, Waterloo Insti-
tute for Nanotechnology, National Sciences and Engineering Coun-
cil of Canada (DG and RTI Funds), Canada Foundation for innova-
tion, and Ontario Research Fund.
[21] H. Senboku, H. Komatsu, Y. Fujimura, M. Tokuda, Efficient electrochemical di-
carboxylation of phenyl-substituted alkenes: synthesis of 1-phenylalkane-1,2-
[22] D.A. Tyssee, M.M. Baizer, Electrocarboxylation. I. Mono- and dicarboxylation of
[23] C. Li, G. Yuan, H. Jiang, Electrocarboxylation of alkynes with carbon dioxide
in the presence of metal salt catalysts, Chin. J. Chem. 28 (2010) 1685–1689,
[25] Y. Qu, C. Tsuneishi, H. Tateno, Y. Matsumura, M. Atobe, Green synthesis of α-
amino acids by electrochemical carboxylation of imines in a flow microreactor,
Supplementary materials
Supplementary material associated with this article can be
[26] C.H. Li, X.Z. Song, L.M. Tao, Q.G. Li, J.Q. Xie, M.N. Peng, L. Pan, C. Jiang,
Z.Y Peng, M.F. Xu, Electrogenerated-bases promoted electrochemical synthe-
sis of N-bromoamino acids from imines and carbon dioxide, Tetrahedron 70
References
[1] A. Kätelhön, R. Meys, S. Deutz, S. Suh, A. Bardow, Climate change mitigation
potential of carbon capture and utilization in the chemical industry, Proc. Natl.
[2] A.S. Agarwal, E. Rode, N. Sridhar, D. Hill, Conversion of CO2 to value-added
chemicals: opportunities and challenges, in: W.Y. Chen, T. Suzuki, M. Lackner
(Eds.), Handbook of Climate Change Mitigation and Adaptation, Springer, New
[3] A. Irabien, M. Alvarez-Guerra, J. Albo, A. D.R., Chapter 2 - Electrochemical con-
version of CO2 to value-added products, in: C.A. Martínez-Huitle, M.A. Ro-
[27] V.E. Titov, V.N. Bondarenko, V.G. Koshechko, Electrochemical activation and
carboxylation of fluorine-containing aromatic imines, Theor. Exp. Chem. 44
[28] V.G. Koshechko, V.E. Titov, V.N. Bondarenko, V.D. Pokhodenko, Electrochemi-
[29] B.R. Buckley, A.P. Patel, K.G.U. Wijayantha-Kahagala-Gamage, ‘Ring-expansion
addition’ of epoxides using applied potential: an investigation of catalysts for
atmospheric pressure carbon dioxide utilization, RSC Adv.
4 (2014) 58581–
[4] R. Shirmohammadi, A. Aslani, R. Ghasempour, L.M. Romeo, CO2 Utilization
via Integration of an Industrial Post-Combustion Capture Process with a Urea
[30] M.D. Otero, B. Batanero, F. Barba, Facile electrochemical transformation of di-
azonium salts into carboxylic acids, Tetrahedron Lett. 47 (2006) 8215–8216,
Plant: Process Modelling and Sensitivity Analysis, Processes
8 (2020) 1144,
[31] P. Tascedda, E. Duñach, Electrosynthesis of cyclic carbamates from aziridines
[32] C. Saboureau, M. Troupel, J. Perichon, Organic electrosynthesis with a sacri-
ficial anode. Chemical reductive degradation of the solvent N,N-dimethyl for-
[33] A.K. Datta, P.A. Marron, C.J.H. King, J.H. Wagenknecht, Process development for
electrocarboxylationof 2-acetyl-6-methoxynaphthalene, J. Appl. Electrochem.
[5] H. Ritchie, M. Roser, CO2 and Greenhouse Gas Emissions, published online
other-greenhouse-gas-emissions’ [Online Resource], 2017.
[6] R. Matthessen, J. Fransaer, K. Binnemans, D.E. De Vos, Electrocarboxylation: to-
wards sustainable and efficient synthesis of valuable carboxylic acids, Beilstein
[7] A. Otto, T. Grube, S. Schiebahn, D. Stolten, Closing the loop: captured CO2 as
a feedstock in the chemical industry, Energy Environ. Sci. 8 (2015) 3283–3297,
[34] O. Scialdone, A. Galia, C. Belfiore, G. Filardo, G. Silvestri, Influence of the exper-
imental system and optimization of the selectivity for the electrocarboxylation
of chloroacetonitrile to cyanoacetic acid, Ind. Eng. Chem. Res. 43 (2004) 5006–
[9] D. Yimin, N. Lanli, L. Hui, Z. Jiaqi, Y. Linping, F. Qiuju, Cu-Ni alloy catalyzed
electrochemical carboxylation of benzyl bromide with carbon dioxide in ionic
liquid 1-butyl-3- methylimidazolium tetrafluoroborate, Int. J. Electrochem. Sci.
[35] D.T. Yang, M. Zhu, Z.J. Schiffer, K. Williams, X. Song, X. Liu, K. Manthiram, Di-
rect electrochemical carboxylation of benzylic C–N bonds with carbon dioxide,
[36] L. Muchez, D.E. De Vos, M.J. Kim, Sacrificial anode-free electrosynthesis
[10] J.J. Medvedev, X.V. Medvedeva, F. Li, T.A. Zienchuk, A. Klinkova, Electrochemical
CO2 fixation to α-methylbenzyl bromide in divided cells with nonsacrificial
anodes and aqueous anolytes, ACS Sustain. Chem. Eng. 7 (2019) 19631–19639,
[11] V. Rajagopal, P. Manivel, N. Nesakumar, M. Kathiresan, D. Velayutham,
V. Suryanarayanan, AgxCuyNiz trimetallic alloy catalysts for the electrocatalytic
reduction of benzyl bromide in the presence of carbon dioxide, ACS Omega 3
[37] H. Senboku, K. Nagakura, T. Fukuhara, S. Hara, Three-component coupling re-
action of benzylic halides, carbon dioxide, and N,N-dimethylformamide by us-
[12] D.F. Niu, L.P. Xiao, A.J. Zhang, G.Rong Zhang, Q.Y. Tan, J.X. Lu, Electrocatalytic
carboxylation of aliphatic halides at silver cathode in acetonitrile, Tetrahedron
[38] S. Wongrakpanich, A. Wongrakpanich, K. Melhado, J. Rangaswami, A compre-
hensive review of non-steroidal anti-inflammatory drug use in the elderly, Ag-
[13] S. Bazzi, G.L. Duc, E. Schulz, C. Gosmini, M. Mellah, CO2 activation by electro-
generated divalent samarium for aryl halide carboxylation, Org. Biomol. Chem.
[40] Y. Zhang, X. Wang, M. Sunkara, Q. Ye, L.V. Ponomereva, Q.B. She, A.J. Morris,
J.S. Thorson, A diastereoselective oxa-Pictet–Spengler-based strategy for (+)-
frenolicin B and epi-(+)-frenolicin B synthesis, Org. Lett. 15 (2013) 5566–5569,
[14] Y.C. Lan, H. Wang, L.X. Wu, S.F. Zhao, Y.Q. Gu, J.X. Lu, Electroreduction of dibro-
mobenzenes on silver electrode in the presence of CO2, J. Electroanal. Chem.
[15] B.L. Chen, Z.Y. Tu, H.W. Zhu, W.W. Sun, H. Wang, J.X. Lu, CO2 as a C1-organic
building block: enantioselective electrocarboxylation of aromatic ketones with
CO2catalyzed by cinchona alkaloids under mild conditions, Electrochim. Acta
[41] K.I. Takao, R. Nanamiya, Y. Fukushima, A. Namba, K. Yoshida, K.I. Tadano, To-
tal synthesis of (+)-clavilactone A and (−)-clavilactone B by ring-opening/ring-
[42] P. Wipf, S.R. Spencer, Asymmetric total syntheses of tuberostemonine, didehy-
drotuberostemonine, and 13-epituberostemonine, J. Am. Chem. Soc. 127 (2005)
[43] Y.F. Huang, D.Y. Wu, A. Wang, B. Ren, S. Rondinini, Z.Q. Tian, C. Amatore, Bridg-
ing the gap between electrochemical and organometallic activation: benzyl
chloride reduction at silver cathodes, J. Am. Chem. Soc. 132 (2010) 17199–
[44] J.J. Medvedev, Y.P. Steksova, X.V. Medvedeva, Y. Pivovarova, E.F. Krivoshapkina,
A. Klinkova, Synthesis of dimeric molecules via Ag-catalyzed electrochemi-
cal homocoupling of organic bromides paired with electrooxidation of urea,
[45] A. Wang, Y. Fan, U.K. Sur, D.Y. Wu, B. Ren, S. Rondinini, C. Amatore, Z.Q. Tian,
In Situ identification of intermediates of benzyl chloride reduction at a silver
electrode by SERS coupled with DFT calculations, J. Am. Chem. Soc. 132 (2010)
[16] S.F. Zhao, H. Wang, Y.C. Lan, X. Liu, J.X. Lu, J. Zhang, Influences of the operative
[17] A.S.C. Chan, T.T. Huang, J.H. Wagenknecht, R.E. Miller, A novel synthesis of 2-
aryllactic acids via electrocarboxylation of methyl aryl ketones, J. Org. Chem.
[18] O. Scialdone, A. Galia, A.A. Isse, A. Gennaro, M.A. Sabatino, R.N Leone, G. Fi-
lardo, Electrocarboxylation of aromatic ketones: Influence of operative param-
eters on the competition between ketyl and ring carboxylation, J. Electroanal.
[19] S.K. Lateef, R.R. Raju, S.K. Mohan, S.J. Reddy, Electrochemical synthesis of α-
hydroxycarboxylic acids from acetophenones, Synth. Commun. 36 (2006) 31–
10