二氧化碳自由基阴离子的应用研究进展

doi:10.6023/cjoc202404039

摘要/Abstract

二氧化碳自由基阴离子( $\mathrm{CO}_{2}^{-\cdot}$ )是一种具有强还原性的活泼化学中间体, 其作为羧基来源和单电子还原剂在有机合成反应及污水还原降解中具有广泛的应用. CO₂和甲酸及甲酸盐是常见的 $\mathrm{CO}_{2}^{-\cdot}$ 来源, 能够通过单电子还原或氢原子转移过程转化为 $\mathrm{CO}_{2}^{-\cdot}$ . 本综述总结了 $\mathrm{CO}_{2}^{-\cdot}$ 产生的机理及表征的方法, 介绍了 $\mathrm{CO}_{2}^{-\cdot}$ 在各应用领域的最新研究进展, 并对 $\mathrm{CO}_{2}^{-\cdot}$ 的应用前景提出了展望.

关键词: 二氧化碳自由基阴离子, Giese自由基加成, 脱氟烷基化, 还原降解

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

引用此文

侯静, 黄燕, 李浩, 万远翠, 邵雨, 詹乐武, 王定海, 李斌栋. 二氧化碳自由基阴离子的应用研究进展[J]. 有机化学, 2024, 44(10): 3117-3135.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 32

图式1. 可见光促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的产生的方法

Scheme 1. Visible-light promoted methods to produce

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式1. 可见光促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的产生的方法

Scheme 1. Visible-light promoted methods to produce

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式2. 电化学促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的产生的方法

Scheme 2. Electrochemistry promoted methods to produce of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式2. 电化学促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的产生的方法

Scheme 2. Electrochemistry promoted methods to produce of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式3. 还原性铜络合物作为催化剂产生

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的机制

Scheme 3. Possible mechanism for the production of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ with copper complexes as reduced catalysts

图式3. 还原性铜络合物作为催化剂产生

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的机制

Scheme 3. Possible mechanism for the production of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ with copper complexes as reduced catalysts

图式4. 其它方法: (a)水处理技术中两种常见的

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 产生方法和(b) Fe3+-柠檬酸盐释放出

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的机制

Scheme 4. Other methods: (a) two common methods in sewage treatment field, and (b) possible mechanism of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ release from Fe3+-citrate

图式4. 其它方法: (a)水处理技术中两种常见的

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 产生方法和(b) Fe3+-柠檬酸盐释放出

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的机制

Scheme 4. Other methods: (a) two common methods in sewage treatment field, and (b) possible mechanism of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ release from Fe3+-citrate

图式5.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的产生及检测

Scheme 5. Production and detection of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式5.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 的产生及检测

Scheme 5. Production and detection of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式6. (a)环己烯双羧化反应; (b)胺的羧化反应; (c)烯烃、芳基硫醇与CO2的硫羧化反应

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

图式7.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的烯烃β-羧基化反应

Scheme 7. β-Carboxylation of olefin with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式7.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的烯烃β-羧基化反应

Scheme 7. β-Carboxylation of olefin with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式8. CTC复合物驱动的烯烃或炔烃的羧基化反应

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

图式9. (a)烯烃、二烯烃和(异)芳烃的双羧化反应; (b)未活化烯烃的双羧化和氢羧化反应

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

图式10. 光促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的非活化烯烃芳羧化反应

Scheme 10. Arylcarboxylation of unactivated alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ via visible-light photoredox catalysis

图式10. 光促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的非活化烯烃芳羧化反应

Scheme 10. Arylcarboxylation of unactivated alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ via visible-light photoredox catalysis

图式11.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的烯烃双官能团反应

Scheme 11. Difunctional reaction of alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式11.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的烯烃双官能团反应

Scheme 11. Difunctional reaction of alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式12. 光促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的烯烃氢羧化反应

Scheme 12. Light-promoted hydrocarboxylation reaction of alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式12. 光促进

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的烯烃氢羧化反应

Scheme 12. Light-promoted hydrocarboxylation reaction of alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式13.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的杂环芳烃羧基化反应

Scheme 13. Carboxylation of (hetero) arenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式13.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 参与的杂环芳烃羧基化反应

Scheme 13. Carboxylation of (hetero) arenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式14.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的选择性羧基化反应和羟羧化反应

Scheme 14. Selective carboxylation reaction and carboxylation reactions induced by

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式14.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的选择性羧基化反应和羟羧化反应

Scheme 14. Selective carboxylation reaction and carboxylation reactions induced by

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式15. 草酸作为

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 来源参与的烯烃选择性氢羧化反应

Scheme 15. Selective hydrocarboxylation of alkenes using oxalic acid as source of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式15. 草酸作为

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 来源参与的烯烃选择性氢羧化反应

Scheme 15. Selective hydrocarboxylation of alkenes using oxalic acid as source of

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式16.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 作为强还原剂参与的可见光驱动的芳基卤化物还原反应

Scheme 16. Visible-light promoted reduction reaction of aryl halide with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ as reducing agent

图式16.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 作为强还原剂参与的可见光驱动的芳基卤化物还原反应

Scheme 16. Visible-light promoted reduction reaction of aryl halide with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ as reducing agent

图式17. 可见光促进的

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的烯烃氧芳化和氢芳化反应

Scheme 17. Visible-light-promoted oxyarylation and hydroarylation of alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式17. 可见光促进的

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的烯烃氧芳化和氢芳化反应

Scheme 17. Visible-light-promoted oxyarylation and hydroarylation of alkenes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式18.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的选择性C(sp3)—F键裂解羧基化反应

Scheme 18. Selective carboxylation reaction via

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ induced cleavage of C(sp3)—F bonds

图式18.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的选择性C(sp3)—F键裂解羧基化反应

Scheme 18. Selective carboxylation reaction via

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ induced cleavage of C(sp3)—F bonds

图式19.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的三氟乙酸乙酯脱氟烷基化反应

Scheme 19. Defluorinative alkylation of trifluoroacetates with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式19.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的三氟乙酸乙酯脱氟烷基化反应

Scheme 19. Defluorinative alkylation of trifluoroacetates with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式20.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的三氟甲基衍生物脱氟烷基化反应

Scheme 20. Defluorinative functionalizations of polyfluorinated aliphatic amides and esters with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式20.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的三氟甲基衍生物脱氟烷基化反应

Scheme 20. Defluorinative functionalizations of polyfluorinated aliphatic amides and esters with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式21. (a)三氟乙酰苯胺脱氟烷基化反应; (b)硫醇作为双功能催化剂诱导的三氟甲基衍生物脱氟烷基化反应

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

图式22. 三氟甲基苯并咪唑脱氟烷基化反应

Scheme 22. Defluorinative alkylation of trifluoromethylbenzimidazoles

图式23. 三氟甲基苯衍生物脱氟烷基化反应

Scheme 23. Defluoroalkylation of trifluoromethylarenes with hydrazones

图式24. 无催化剂添加的三氟甲基衍生物脱氟烷基化反应

Scheme 24. Catalyst-free defluorinative alkylation of trifluoromethyls

图式25. 烯烃的选择性β-氢羧化反应

Scheme 25. Selective β-hydrocarboxylation of substituted olefins

图式26.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的芳烃氧杂环选择性电羧化反应

Scheme 26. Selective electrocarboxylation of styrene oxides with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式26.

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的芳烃氧杂环选择性电羧化反应

Scheme 26. Selective electrocarboxylation of styrene oxides with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式27. 电化学还原

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的非活化二烯双羧化反应

Scheme 27. Electroreductive dicarboxylation of unactivated skipped dienes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式27. 电化学还原

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$ 诱导的非活化二烯双羧化反应

Scheme 27. Electroreductive dicarboxylation of unactivated skipped dienes with

{C O}_{2}^{- \cdot}

$\mathrm{CO}_{2}^{-\cdot}$

图式28. 多取代乙烷中的C(sp3)—C(sp3)键与CO2的电还原羧化反应

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

图式29. 可见光诱导的4-硝基苯胺还原反应

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

图式30. Cr(VI)还原降解的可能机制

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

图式31. UV/

C_{2} O_{4}^{2}

${{\text{C}}_{2}}\text{O}_{4}^{2}$ /Fe3+体系中

{NO}_{3}^{-}

$\text{NO}_{3}^{-}$ 还原过程及产物形成途径

Scheme 31. Proposed pathways for reduction of

{NO}_{3}^{-}

$\text{NO}_{3}^{-}$ and their product formation in the UV/

C_{2} O_{4}^{2}

${{\text{C}}_{2}}\text{O}_{4}^{2}$ /Fe3+ process

图式31. UV/

C_{2} O_{4}^{2}

${{\text{C}}_{2}}\text{O}_{4}^{2}$ /Fe3+体系中

{NO}_{3}^{-}

$\text{NO}_{3}^{-}$ 还原过程及产物形成途径

Scheme 31. Proposed pathways for reduction of

{NO}_{3}^{-}

$\text{NO}_{3}^{-}$ and their product formation in the UV/

C_{2} O_{4}^{2}

${{\text{C}}_{2}}\text{O}_{4}^{2}$ /Fe3+ process

图式32. 热活化过硫酸盐体系中DDT还原脱氯氧化降解的可能机制

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

参考文献 102

[1]	Koppenol, W. H.; Rush, J. D. J. Phys. Chem. 1987, 91, 4429.
[2]	Majhi, J.; Molander, G. A. Angew. Chem., Int. Ed. 2023, 63, e202311853.
[3]	Xiao, W.; Zhang, J.; Wu, J. ACS Catal. 2023, 13, 15991.
[4]	Gui, Y. Y.; Yan, S. S.; Yu, D. G. Sci. Bull. 2023, 68, 3124.
[5]	Rooso, J. A.; Bertolotti, S. G.; Braun, A. M. J. Phys. Org. Chem. 2001, 14, 300.
[6]	Arias-Rotondo, D. M.; Mccusker, J. K. Chem. Soc. Rev. 2016, 45, 5803. pmid: 27711624
[7]	Ghosh, S.; Majumder, S.; Ghosh, D.; Hajra, A. Chem. Commun. 2023, 59, 7004.
[8]	Chalotra, N.; Kumar, J.; Naqvi, T.; Shah, B. A. Chem. Commun. 2021, 57, 11285.
[9]	Bao, X.; Yu, W.; Wang, G. Adv. Synth. Catal. 2023, 365, 2299.
[10]	Sivanandan, S. T.; Jesline, M. J.; Nair, D. K.; Kumar, T. Asian J. Org. Chem. 2023, 12, e202200555.
[11]	Matsumoto, A. J. Synth. Org. Chem., Jpn. 2022, 80, 868.
[12]	Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470.
[13]	Seo, H.; Katcher, M. H.; Jamison, T. F. Nat. Chem. 2017, 9, 453.
[14]	Seo, H.; Liu, A.; Jamison, T. F. J. Am. Chem. Soc. 2017, 139, 13969.
[15]	Ye, J. H.; Miao, M.; Huang, H.; Yan, S. S.; Yin, Z. B.; Zhou, W. J.; Yu, D. G. Angew. Chem., Int. Ed. 2017, 56, 15416.
[16]	Huang, H.; Ye, J. H.; Zhu, L.; Ran, C. K.; Miao, M.; Wang, W.; Chen, H. J.; Zhou, W. J.; Lan, Y.; Yu, B.; Yu, D. G. CCS Chem. 2020, 2, 1746.
[17]	Miao, M.; Zhu, L.; Zhao, H.; Song, L.; Yan, S. S.; Liao, L. L.; Ye, J. H.; Lan, Y.; Yu, D. G. Sci. China Chem. 2023, 66, 1457.
[18]	Zhang, W.; Chen, Z.; Jiang, Y. X.; Liao, L. L.; Wang, W.; Ye, J. H.; Yu, D. G. Nat. Commun. 2023, 14, 3529. doi: 10.1038/s41467-023-39240-8 pmid: 37316537
[19]	Liao, L. L.; Wang, Z. H.; Cao, K. G.; Sun, G. Q.; Zhang, W.; Ran, C. K.; Li, Y. W.; Chen, L.; Cao, G. M.; Yu, D. G. J. Am. Chem. Soc. 2022, 144, 2062.
[20]	Zhang, W.; Liao, L. L.; Li, L.; Liu, Y.; Dai, L. F.; Sun, G. Q.; Ran, C. K.; Ye, J. H.; Lan, Y.; Yu, D. G. Angew. Chem., Int. Ed. 2023, 62, e202301892.
[21]	Yan, S. S.; Liu, S. H.; Chen, L.; Bo, Z. Y.; Jing, K.; Gao, T. Y.; Yu, B.; Lan, Y.; Luo, S. P.; Yu, D. G. Chem 2021, 7, 3099.
[22]	Sun, G. Q.; Yu, P.; Zhang, W.; Wang, Y.; Liao, L. L.; Zhang, Z.; Lu, Z. P.; Lin, S.; Yu, D. G. Nature 2023, 615, 67.
[23]	Wang, H.; Gao, Y. Z.; Zhou, C. L.; Li, G. J. Am. Chem. Soc. 2020, 142, 8122. doi: 10.1021/jacs.0c03144 pmid: 32309942
[24]	Wang, H.; Jui, N. T. J. Am. Chem. Soc. 2018, 140, 163.
[25]	Vogt, D. B.; Seath, C. P.; Wang, H. B.; Jui, N. T. J. Am. Chem. Soc. 2019, 141, 13203.
[26]	Hendy, C. M.; Smith, G. C.; Xu, Z. H.; Lian, T. Q.; Jui, N. T. J. Am. Chem. Soc. 2021, 143, 8987.
[27]	Maust, C. M.; Hendy, C. M.; Jui, N. T.; Blakey, S. B. J. Am. Chem. Soc. 2022, 144, 3776. doi: 10.1021/jacs.2c00192 pmid: 35200024
[28]	Alektiar, S. N.; Wickens, Z. K. J. Am. Chem. Soc. 2021, 143, 13022. doi: 10.1021/jacs.1c07562 pmid: 34380308
[29]	Alektiar, S. N.; Han, J.; Dang, Y.; Rubel, C. Z.; Wickens, Z. K. J. Am. Chem. Soc. 2023, 145, 10991. doi: 10.1021/jacs.3c03671 pmid: 37186951
[30]	Mikhael, M.; Alektiar, S. N.; Wickens, Z. K. Angew. Chem., Int. Ed. 2023, 62, e202303264.
[31]	Huang, Y.; Hou, J.; Zhan, L. W.; Zhang, Q.; Tang, W. Y.; Li, B. D. ACS Catal. 2021, 11, 15004.
[32]	Huang, Y.; Zhang, Q.; Zhan, L. W.; Hou, J.; Li, B. D. Chin. J. Org. Chem. 2022, 42, 2568. (in Chinese)
	(黄燕, 张谦, 詹乐武, 侯静, 李斌栋, 有机化学, 2022, 42, 2568.) doi: 10.6023/cjoc202202008
[33]	Huang, Y.; Zhang, Q.; Hua, L. L.; Zhan, L. W.; Hou, J.; Li, B. D. Cell Rep. Phys. Sci. 2022, 3, 100994.
[34]	Hou, J.; Hua, L. L.; Huang, Y.; Zhan, L. W.; Li, B. D. Chem. Asian J. 2022, e202201092.
[35]	Zhang, L. H.; Zhu, D.; Nathanson, G. M.; Hamers, R. J. Angew. Chem., Int. Ed. 2014, 53, 9746.
[36]	Khoshro, H.; Zare, H. R.; Vafazadeh, R. J. CO₂ Util. 2015, 12, 77.
[37]	Ma, F.; Miao, T.; Zhou, Z. J.; Xu, H. L. RSC Adv. 2016, 6, 851.
[38]	Xu, J. Y.; Kan, Y. H.; Huang, R.; Zhang, B. S.; Wang, B.; Wu, K. H.; Lin, Y. M.; Sun, X. Y.; Li, Q. F.; Centi, G.; Su, D. S. ChemSus- Chem 2016, 9, 1085.
[39]	Lei, F. C.; Liu, W.; Sun, Y. F.; Xu, J. Q.; Liu, K.; Liang, L.; Yao, T.; Pan, B.; Wei, S.; Xie, Y. Nat. Commun. 2016, 7, 12697.
[40]	Mora, V. C.; Rosso, J. A.; Mártire, D. O.; Gonzalez, M. C.; Roux, G. C. L. Chemosphere 2009, 75, 1405.
[41]	Gu, X.; Lu, S.; Fu, X.; Qiu, Z. F.; Sui, Q.; Guo, X. H. Sep. Purif. 2017, 172, 211.
[42]	Gao, L.; Gu, X. G.; Lu, Z. H. China Environ. Sci. 2016, 36, 2645.
[43]	Tachikawa, T.; Tojo, S.; Fujitsuka, M.; Majima, T. Langmuir 2004, 20, 9441. pmid: 15491173
[44]	Villamena, F. A.; Locigno, E. J.; Rockenbauer, A.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2006, 110, 13253.
[45]	Berkovic, A. M.; Gonzalez, M. C.; Russo, N.; Michelini, M. C.; Diez, R. P.; Mártire, D. O. J. Phys. Chem. A 2010, 114, 12845. doi: 10.1021/jp106035m pmid: 21086971
[46]	Subelzu, N.; Schöneich, C. Mol. Pharm. 2020, 17, 4163.
[47]	Zhang, Y. L.; Richards, D. S.; Grotemeyer, E. N.; Jackson, T. A.; Schöneich, C. Mol. Pharm. 2022, 19, 4026.
[48]	Amatore, C.; Savéant, J. M. J. Am. Chem. Soc. 1981, 103, 5021.
[49]	Matsuoka, S.; Kohzuki, T.; Yanagida, S.; Pac, C.; Ishida, A.; Takamuku, S.; Kusaba, M.; Nakashima, N.; Yanagida, S. J. Phys. Chem. B 1992, 96, 4437.
[50]	Meerholz, K.; Heinze, J. J. Am. Chem. Soc. 1989, 111, 2326.
[51]	Isse, A. A.; Gennaro, A. Chem. Commun. 2002, 2798.
[52]	Kai, T.; Zhou, M.; Duan, Z. Y.; Henkelman, G. A.; Bard, A. J. J. Am. Chem. Soc. 2017, 139, 18552.
[53]	Lamy, E.; Nadjo, L.; Saveant, J. M. J. Electroanal. Chem. 1977, 78, 403.
[54]	Hammouche, M.; Lexa, D.; Momenteau, M.; Savéant, J. M. J. Am. Chem. Soc. 1991, 113, 8455.
[55]	Ito, T.; Hata, H.; Nishimoto, S. Int. J. Radiat. 2000, 76, 683.
[56]	Eugenio, S. M.; Clifford, P. K. Organometallics 2005, 24, 96.
[57]	Li, J.; Inagi, S.; Fuchigami, T.; Hosono, H.; Ito, S. Electrochem. Commun. 2014, 44, 45.
[58]	Liu, X. W.; Zhong, J.; Fang, L.; Wang, L. L.; Ye, M.; Shao, Y.; Li, J.; Zhang, T. Chem. Eng. J. 2016, 303, 56.
[59]	Qin, B. Y.; Tang, H.; Xu, J. P. China Environ. Sci. 2018, 38, 2505.
[60]	Li, B. Z. Shanghai Environ. Sci. 2019, 38, 47.
[61]	Grills, D. C.; Lymar, S. V. Phys. Chem. Chem. Phys. 2018, 20, 10011. doi: 10.1039/c8cp00977e pmid: 29620127
[62]	Ju, T.; Zhou, Y. Q.; Cao, K. G.; Fu, Q.; Ye, J. H.; Sun, G. S.; Liu, X. F., Chen, L.; Liao, L. L.; Yu, D. G. Nat. Catal. 2021, 4, 304.
[63]	Song, L.; Wang, W.; Yue, J. P.; Jiang, Y. X.; Wei, M. K.; Zhang, H. P.; Yan, S. S.; Liao, L. L.; Yu, D. G. Nat. Catal. 2022, 5, 832.
[64]	Zhou, C. L.; Wang, X. C.; Yang, L.; Fu, L.; Li, G. Green Chem. 2022, 24, 6100.
[65]	Fu, M. C.; Wang, J. X.; Ge, W.; Du, F. M.; Fu, Y. Org. Chem. Front. 2023, 10, 35.
[66]	Xu, P.; Wang, S.; Liu, Y. Q.; Li, R. B.; Liu, W. W.; Wang, X. P.; Zou, M. L.; Zhou, Y.; Guo, D.; Zhu, X. ACS Catal. 2023, 13, 2149.
[67]	Zhang, F. L.; Wu, X. Y.; Gao, P. P.; Zhang, H.; Li, Z.; Ai, S.; Li, G. Chem. Sci. 2024, 15, 6178.
[68]	Mangaonkar, S. R.; Hayashi, H.; Takano, H.; Kanna, W.; Maeda, S.; Mita, T. ACS Catal. 2023, 13, 2482.
[69]	Wu, Z. G.; Wu, M. Y.; Zhu, K.; Wu, J.; Lu, Y. X. Chem 2023, 9, 978.
[70]	Alyah, F. C.; Oliver, P. W.; Chernowsky, C. P.; Yeung, C. S.; Wickens, Z. K. J. Am. Chem. Soc. 2021, 143, 10882.
[71]	Campbell, M. W.; Polites, V. C.; Patel, S.; Lipson, J. E.; Majhi, J.; Molander, G. A. J. Am. Chem. Soc. 2021, 143, 19648. doi: 10.1021/jacs.1c11059 pmid: 34793157
[72]	Ye, J. H.; Bellotti, P.; Heusel, C.; Glorius, F. Angew. Chem., Int. Ed. 2022, 61, e202115456.
[73]	Liu, C.; Shen, N.; Shang, R. Nat. Commun. 2022, 13, 354.
[74]	Liu, C.; Li, K.; Shang, R. ACS Catal. 2022, 12, 4103.
[75]	Xu, P.; Wang, X. Y.; Wang, Z. J.; Zhao, J. J.; Cao, X. D.; Xiong, X. C.; Yuan, Y. C.; Zhu, S.; Guo, D.; Zhu, X. Org. Lett. 2022, 24, 4075.
[76]	Hendy, C. M.; Pratt, C. J.; Jui, N. T.; Blakey, S. B. Org. Lett. 2023, 25, 1397.
[77]	Saini, V.; Stokes, B. J.; Sigman, M. S. Angew. Chem., Int. Ed. 2013, 52, 11206.
[78]	Juliá, F.; Yan, J.; Paulus, F.; Ritter, T. J. Am. Chem. Soc. 2021, 143, 12992.
[79]	Yu, J. J.; Zhang, X.; Wu, X.; Zhang, Z. Q.; Wu, J.; Zhu, C. Chem 2023, 9, 472.
[80]	Huang, Y.; Wan, Y. C.; Shao, Y.; Zhan, L. W.; Hou, J.; Li, B. D. Green Chem. 2023, 25, 8280.
[81]	Herburger, A.; Oncak, M.; Barwa, E.; Linde, C.V.; Beyer, M. K. Int. J. Mass Spectrom. 2019, 435, 101. doi: 10.1016/j.ijms.2018.10.019 pmid: 33209089
[82]	Cencer, M. M.; Li, C. Y.; Agarwal, G.; Neto, R. J.; Amanchukwu, C.V.; Assary, R. S. ACS Omega 2022, 7, 18131.
[83]	Alkayal, A.; Tabas, V.; Montanaro, S.; Wright, L. A.; Malkov, A. V.; Buckley, B. R. J. Am. Chem. Soc. 2020, 142, 1780. doi: 10.1021/jacs.9b13305 pmid: 31960672
[84]	You, Y.; Kanna, W.; Mita, T. J. Am. Chem. Soc. 2022, 144, 3685.
[85]	Zhao, L.; Xie, W. J.; Li, H. R.; He, L. N. Org. Lett. 2024, 26, 3241. doi: 10.1021/acs.orglett.4c00860 pmid: 38578088
[86]	Zhang, K.; Ren, B. H.; Liu, X. F.; Wang, L. L.; Zhang, M.; Ren, W. M.; Lu, X. B.; Zhang, W. Z. Angew. Chem., Int. Ed. 2022, 61, e202207660.
[87]	Wang, Y. W.; Tang, S. Y.; Qiu, Y. A. Angew. Chem., Int. Ed. 2022, 61, e202207746.
[88]	Ran, C.-K.; Qu, Q.; Tao, Y.-Y.; Chen, Y.-F.; Liao, L.-L.; Ye, J.-H.; Yu, D.-G. Sci. China Chem. 2024, 67, 3366.
[89]	Rosso, J. A.; Bertolotti, S. G.; Braun, A. M.; Mártire, D. O.; Gonzalez, M. C. J. Phys. Org. Chem. 2001, 14, 300.
[90]	Tachikawa, T.; Tojo, F. M.; Fujitsuka, M.; Majima, T. Langmuir 2004, 20, 9441. pmid: 15491173
[91]	Schutz, O.; Meyerstein, D. Tetrahedron Lett. 2006, 47, 1093.
[92]	Mora, V. C.; Ross, J. A.; Carrillo, L. R.; Mártire, D. O.; Gonzalez, M. C. Chemosphere 2009, 75, 1405.
[93]	Liu, X. W.; Fang, L.; Wang, L. L.; Ye, M. M.; Shao, Y.; Li, J.; Zhang, T. Q. Chem. Eng. J. 2016, 303, 56.
[94]	Wu, W. M.; Liu, G. D.; Liang, S. J.; Chen, Y.; Shen, L. J.; Zhen, H. R.; Yuan, R. S.; Hou, Y. D.; Wu, L. J. Catal. 2012, 290, 13.
[95]	Liu, Y. X.; Wang, L.; Wu, F.; Deng, N. S. Desalin. Water Treat. 2013, 51, 7194.
[96]	Liu, X. W.; Zhong, J. E.; Fang, L.; Wang, L. L.; Ye, M. M.; Shao, Y.; Li, J.; Zhang, T. Q. Chem. Eng. J. 2016, 303, 56.
[97]	Ren, H. J.; Hou, Z. M.; Hou, Z. M.; Ren, H. J.; Hou, Z. M.; Han, X.; Zhou, R. Chem. Eng. J. 2017, 309, 638.
[98]	Amina; Si, X. Y.; Wu, K.; Si, Y. B.; Yousaf, B. Chem. Eng. J. 2020, 384, 123360.
[99]	AlSalka, Y.; Al-Madanat, O.; Curti, M.; Hakki, A.; Bahnemann, D. W. ACS Appl. Energy Mater. 2020, 3, 6678.
[100]	Prajapati, I.; Subelzu, N.; Zhang, Y. L.; Wu, Y. Q.; Schöneich, C. J. Pharm. Sci. 2022, 111, 991.
[101]	Shi, Z. Y.; Wang, F. L.; Xiao, Q.; Yu, S. L.; Ji, X. L. Catalysts 2022, 12, 348.
[102]	Qu, J. H.; Tian, X.; Zhang, X. B.; Yao, J. Y.; Xue, J. Q.; Li, K. G.; Zhang, B.; Zhang, Y. Appl. Catal., B 2022, 310, 121359.