Recent Advances in the Application of Carbon Dioxide Radical Anion

doi:10.6023/cjoc202404039

Abstract

Carbon dioxide radical anion ($\mathrm{CO}_{2}^{-\cdot}$) is an active chemical intermediate with strong reduction ability, which is used widely as C1-building block and single electron reducing reagent in organic synthesis. CO₂ and formic acid or formate salts are common source of $\mathrm{CO}_{2}^{-\cdot}$. $\mathrm{CO}_{2}^{-\cdot}$ can be generated by either direct reduction of CO₂ or hydrogen atom transfer (HAT) of formate salts. The production, characterization methods and application of $\mathrm{CO}_{2}^{-\cdot}$ are summarized, and the insights are provided into the prospects in this field.

Key words: carbon dioxide radical anion, Giese radical addition, defluorinative alkylation, reductive degradation

Cite this article

Jing Hou, Yan Huang, Hao Li, Yuancui Wan, Yu Shao, Lewu Zhan, Dinghai Wang, Bindong Li. Recent Advances in the Application of Carbon Dioxide Radical Anion[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3117-3135.

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Fig. & Tab. 32

Scheme 1. Visible-light promoted methods to produce $\mathrm{CO}_{2}^{-\cdot}$

Scheme 2. Electrochemistry promoted methods to produce of $\mathrm{CO}_{2}^{-\cdot}$

Scheme 3. Possible mechanism for the production of $\mathrm{CO}_{2}^{-\cdot}$ with copper complexes as reduced catalysts

Scheme 4. Other methods: (a) two common methods in sewage treatment field, and (b) possible mechanism of $\mathrm{CO}_{2}^{-\cdot}$ release from Fe3+-citrate

Scheme 5. Production and detection of $\mathrm{CO}_{2}^{-\cdot}$

Scheme 6. (a) Dicarboxylation of cyclohexene; (b) α-carboxylation of amines; (c) thiocarboxylation of styrenes and acrylates with CO2

Scheme 7. β-Carboxylation of olefin with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 8. CTC-complex driven carboxylation reaction of alkenes or alkyne

Scheme 9. (a) Dicarboxylation of alkenes, allenes and (hetero) arenes; (b) Di- and hydrocarboxylation of unactivated alkenes

Scheme 10. Arylcarboxylation of unactivated alkenes with $\mathrm{CO}_{2}^{-\cdot}$ via visible-light photoredox catalysis

Scheme 11. Difunctional reaction of alkenes with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 12. Light-promoted hydrocarboxylation reaction of alkenes with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 13. Carboxylation of (hetero) arenes with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 14. Selective carboxylation reaction and carboxylation reactions induced by $\mathrm{CO}_{2}^{-\cdot}$

Scheme 15. Selective hydrocarboxylation of alkenes using oxalic acid as source of $\mathrm{CO}_{2}^{-\cdot}$

Scheme 16. Visible-light promoted reduction reaction of aryl halide with $\mathrm{CO}_{2}^{-\cdot}$ as reducing agent

Scheme 17. Visible-light-promoted oxyarylation and hydroarylation of alkenes with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 18. Selective carboxylation reaction via $\mathrm{CO}_{2}^{-\cdot}$ induced cleavage of C(sp3)—F bonds

Scheme 19. Defluorinative alkylation of trifluoroacetates with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 20. Defluorinative functionalizations of polyfluorinated aliphatic amides and esters with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 21. (a) Defluoroalkylation and hydrodefluorination of trifluoromethyls; (b) arenethiolate as a dual function catalyst for photocatalytic defluoroalkylation of trifluoromethyls

Scheme 22. Defluorinative alkylation of trifluoromethylbenzimidazoles

Scheme 23. Defluoroalkylation of trifluoromethylarenes with hydrazones

Scheme 24. Catalyst-free defluorinative alkylation of trifluoromethyls

Scheme 25. Selective β-hydrocarboxylation of substituted olefins

Scheme 26. Selective electrocarboxylation of styrene oxides with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 27. Electroreductive dicarboxylation of unactivated skipped dienes with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 28. Electroreductive carboxylation of C(sp3)—C(sp3) bonds in multi-substituted ethane with CO2

Scheme 29. Visible-light-induced reduction of 4-nitroaniline

Scheme 30. Possible mechanism for the Cr(VI) reduction

Scheme 31. Proposed pathways for reduction of $\text{NO}_{3}^{-}$ and their product formation in the UV/${{\text{C}}_{2}}\text{O}_{4}^{2}$/Fe3+ process

Scheme 32. Proposed reductive dechlorination followed by oxidative degradation mechanisms for DDT decomposition in the heat/PS/OA system

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