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Electrocarboxylation of CO2 with Organic Substrates: Toward Cathodic Reaction

Transactions of Tianjin University volume 29, pages 254–274 (2023)Cite this article

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.

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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

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Acknowledgements

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

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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

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  3. Chengguang Yue
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  4. Bangman Feng
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  9. Xinbin Ma
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Correspondence to Mei-Yan Wang or Xinbin Ma.

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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.

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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

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