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Review
. 2023 Jan 10:10:956502.
doi: 10.3389/fchem.2022.956502. eCollection 2022.

Electrochemical organic reactions: A tutorial review

Affiliations
Review

Electrochemical organic reactions: A tutorial review

Joyeeta Lodh et al. Front Chem. .

Abstract

Although the core of electrochemistry involves simple oxidation and reduction reactions, it can be complicated in real electrochemical organic reactions. The principles used in electrochemical reactions have been derived using physical organic chemistry, which drives other organic/inorganic reactions. This review mainly comprises two themes: the first discusses the factors that help optimize an electrochemical reaction, including electrodes, supporting electrolytes, and electrochemical cell design, and the second outlines studies conducted in the field over a period of 10 years. Electrochemical reactions can be used as a versatile tool for synthetically important reactions by modifying the constant electrolysis current.

Keywords: CO2 reduction; electrocatalysis; electrochemical techniques and methods; kinetics; organic reaction.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
Schematic for an undivided electrochemical cell.
FIGURE 2
FIGURE 2
The undivided and divided cell configuration of electrochemical cell used in electroorganic synthesis.
FIGURE 3
FIGURE 3
Schematic for a divided electrochemical cell.
FIGURE 4
FIGURE 4
Different reaction pathways under coupled chemical process.
FIGURE 5
FIGURE 5
Strategies for different electrochemical cross-coupling, oxidative amination, C-N bond formation, and C-H imidation.
FIGURE 6
FIGURE 6
The challenge of electrochemical C-H activation.
FIGURE 7
FIGURE 7
Schematic comparing electrochemical Ullmann thiolation with conventional Ullmann coupling.
FIGURE 8
FIGURE 8
Electrochemical approaches for the generation of Trifluoromethyl radical.
FIGURE 9
FIGURE 9
(A) Proposed single site mechanism of CO2 reduction using Co corrole. (B) (a) EAS of Mn corrole in acetonitrile under argon (black solid line), the chemically reduced form in the presence of KC8 (red dotted line), after the addition of water (blue, dashed line), and subsequent dosage of CO2 (green solid line). (b–d) Potential dependent SEC-UV/Vis of 0.7 mm Mn corrole in acetonitrile with 2% water and 0.2 M TBAPF6 as electrolyte after 2 min CPE (b) under argon, (c) under CO2, and (d) comparison of UV/Vis spectra observed at −1.3 V vs. NHE under argon (black) and CO2 dosage (red). SEC-UV/V measurements were recorded with a light transparent platinum mini-grid as working, as counter, and an Ag-microwire as a pseudo-reference electrode.
FIGURE 10
FIGURE 10
A representative diagram for electro-catalyzed C-H annulations.

References

    1. Adams R. N. (1969). Anodic oxidation pathways of aromatic hydrocarbons and amines. Acc. Chem. Res. 2, 175–180. 10.1021/ar50018a003 - DOI
    1. Adeli Y., Huang K., Liang Y., Jiang Y., Liu J., Song S., et al. (2019). Electrochemically oxidative C–C bond cleavage of alkylarenes for anilines synthesis. ACS Catal. 9, 2063–2067. 10.1021/acscatal.8b04351 - DOI
    1. Agarwal J., Shaw T. W., Schaefer H. F., Iii, Bocarsly A. B. (2015). Design of a catalytic active site for electrochemical CO2 reduction with Mn (I)-tricarbonyl species. Inorg. Chem. 54, 5285–5294. 10.1021/acs.inorgchem.5b00233 - DOI - PubMed
    1. Aljabour A., Apaydin D. H., Coskun H., Ozel F., Ersoz M., Stadler P., et al. (2016). Improvement of catalytic activity by nanofibrous CuInS2 for electrochemical CO2 reduction. ACS Appl. Mat. Interfaces 8, 31695–31701. 10.1021/acsami.6b11151 - DOI - PubMed
    1. Allen B. D., Hareram M. D., Seastram A. C., Mcbride T., Wirth T., Browne D. L., et al. (2019). Manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols via alkoxy radicals. Org. Lett. 21, 9241–9246. 10.1021/acs.orglett.9b03652 - DOI - PMC - PubMed

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