Recent Advances in Photocatalytic Carboxylation Based on Free Radical Process

doi:10.6023/cjoc202405041

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (10): 2961-2996.DOI: 10.6023/cjoc202405041 Previous Articles Next Articles

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基于自由基机理光催化羧基化反应研究进展

李文珂^a,†, 孙北奇^b,†, 张雷^a^,^*(), 莫凡洋^a^,^c^,^*()

a 北京大学工学院北京 100091
b 中国华能集团清洁能源技术研究院有限公司北京 102209
c 北京大学材料科学与工程学院北京 100091

收稿日期:2024-09-05 修回日期:2024-09-21 发布日期:2024-10-11
作者简介:^†共同第一作者
基金资助:
国家自然科学基金(22071004); 国家自然科学基金(21933001); 国家自然科学基金(22150013); 华能集团清洁能源技术研究院基金(CERI/TY-24-CERI02)

Recent Advances in Photocatalytic Carboxylation Based on Free Radical Process

Wenke Li^a,†, Beiqi Sun^b,†, Lei Zhang^a^,^*(), Fanyang Mo^a^,^c^,^*()

a College of Engineering, Peking University, Beijing 100091
b Huaneng Clean Energy Research Institute, Beijing 102209
c School of Material Science and Engineering, Peking University, Beijing 100091

Received:2024-09-05 Revised:2024-09-21 Published:2024-10-11
Contact: *E-mail: lei_zhang@pku.edu.cn;fmo@pku.edu.cn
About author:^†These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22071004); National Natural Science Foundation of China(21933001); National Natural Science Foundation of China(22150013); Foundation of Huaneng Clean Energy Research Institute(CERI/TY-24-CERI02)

Carbon dioxide (CO₂) exerts a significant influence on climate change as a potent greenhouse gas. From a chemical standpoint, CO₂ serves as an abundant and cost-effective “carbon one (C1)” resource with non-toxicity, renewability, and easy obtainability. The utilization of CO₂ for synthesizing high-value-added chemicals represents an important avenue for addressing national strategic requirements and aligning with China’s objectives of peaking carbon emissions by 2030 and achieving carbon neutrality by 2060. Organic photocatalysis can harness light energy to induce electron transfer in organic chemical reactions, facilitating bond cleavage and recombination processes. This approach offers advantages such as mild reaction conditions, environmental friendliness and exceptional selectivity. By integrating CO₂ resource utilization with organic photocatalysis, novel opportunities arise for enriching carboxylation reactions. Two distinct types of photocatalytic carboxylation reactions, those involving carbon anions as pivotal intermediates and those featuring CO₂ radical anions as key intermediates, are systematically elucidated.

Key words: photocatalysis, carbon dioxide (CO₂), carboxylation, carbanion, carbon dioxide radical anion

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Wenke Li, Beiqi Sun, Lei Zhang, Fanyang Mo. Recent Advances in Photocatalytic Carboxylation Based on Free Radical Process[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 2961-2996.

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Fig. & Tab. 59

Scheme 1. Photocatalytic difunctionalization of aryl alkenes

Scheme 2. Visible-light photocatalytic silocarboxylation and carboxylation of alkenes

Scheme 3. Visible-light photocatalytic phosphonocarboxylation of activated alkenes involving CO2

Scheme 4. Visible-light photocatalytic carboxylation of styrene with CO2 and aryl halides

Scheme 5. Photocatalytic difunctionalization of activated alkenes with CO2 and amine

Scheme 6. Bifunctional modification of alkenes by amino acids

Scheme 7. Visible-light catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2

Scheme 8. Visible-light-driven alkene carboxylation using CO2 without photocatalysts

Scheme 9. Visible-light-driven arylcarboxylation of enamides with CO2 and aryl iodides

Scheme 10. Visible-light-driven carboxylation of remote C(sp3)—H with CO2 via a 1,5-hydrogen migration

Scheme 11. Visible-light-driven deconstructive carboxylation of activated alkenes with CO2

Scheme 12. Visible-light-driven carboxylation of alkenes with CO2 through breaking of carbon-carbon double bond

Scheme 13. Visible-light-driven carboxylation of 1,3-diene

Scheme 14. Visible-light-driven direct carboxylation of benzyl C(sp3)—H involving CO2

Scheme 15. Visible-light-driven carboxylation of remote C(sp3)—H involving CO2

Scheme 16. Visible-light-driven dicarboxylation of strained C—C bonds with CO2

Scheme 17. Visible-light induced carboxylation of benzylic C(sp3)—H bonds via 1,5-hydrogen atom transfer

Scheme 18. Visible-light-driven carboxylation of acrylamide and enimide with CO2

Scheme 19. Visible-light-driven carboxylation of arylimine with CO2

Scheme 20. Visible-light-driven carboxylation of cyclic oxime esters with CO2

Scheme 21. Visible-light-driven carboxylation of C—N bonds in quaternary ammonium salts with CO2

Scheme 22. Visible-light-driven carboxylation of C—N bonds in cyclamine with CO2

Scheme 23. Visible-light-driven carboxylation of benzyl halides with CO2

Scheme 24. Visible-light-driven carboxylation of benzyl bromides with CO2

Scheme 25. Visible-light-driven carboxylation of benzyl chlorine with CO2

Scheme 26. Visible-light-driven carboxylation of benzyl halides C—F bonds with CO2

Scheme 27. Visible-light-driven carboxylation of polyfluoroaromatic hydrocarbons C—F bonds with CO2

Scheme 28. Visible-light-driven carboxylation of acylsilane with CO2

Scheme 29. Visible-light-driven carboxylation of carbonyl compound with CO2

Scheme 30. Visible-light-driven carboxylation of aromatic aldehydes or ketones with CO2

Scheme 31. Visible-light-driven carboxylation of C(sp3)—O bonds with CO2

Scheme 32. Visible-light-driven carboxylation of benzyl alcohol C(sp3)—O bonds with CO2

Scheme 33. Visible-light-driven carboxylation of aryl epoxides with CO2

Scheme 34. Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis

Scheme 35. Carboxylation of nonactivated arenes with CO2 via visible-light-induced reductive dearomatization

Scheme 36. Visible-light photocatalytic dearomatization/carboxylation of benzyl o-halogenated aryl ethers with CO2

Scheme 37. Visible light catalyzed dearomatization and carboxylation of indole with CO2

Scheme 38. Visible light catalyzed intermolecular α-aminomethyl/carboxylative dearomatization of indoles with CO2

Scheme 39. UV-light-driven inverse martensitic carboxylation of styrene with CO2?-

Scheme 40. UV-light-driven carboxylation of amine with CO2?-

Scheme 41. Visible-light-driven iron-promoted carboxylation of alkenes and phenylthiophenol with CO2

Scheme 42. Photoiodocarboxylation of activated alkenes

Scheme 43. Visible-light-driven metal free carboxylation of alkenes with CO2?-

Scheme 44. Visible light-driven metal free carboxylation of alkynes with $\mathrm{CO}_{2}^{-\cdot}$

Scheme 45. Visible light-driven metal free carboxylation of inactive alkenes with CO2

Scheme 46. Visible-light-driven carboxylation of alkenes with CO2?-

Scheme 47. Visible-light-driven carboxylation of alkenes using formate as carbon source under heating condition

Scheme 48. Visible-light-driven hydrocarboxylation of activated alkene using formate as carbon source

Scheme 49. Visible-light-driven hydrocarboxylation of inert alkene using formate as carbon source

Scheme 50. Visible-light-driven synthesis of α-amino acids using formate as carbon source

Scheme 51. Visible-light-driven dearomative carboxylation of (hetero)aromatics under heating condition

Scheme 52. Photocatalytic coupling reaction of electron-deficient olefin

Scheme 53. Carboxylation of alkenes in air using formate as carbon source

Scheme 54. Photocatalytic defluorinated carboxylation using formate as reducing agent and carbon source

Scheme 55. Visible-light-driven defluorinated carboxylation of α-trifluoromethyl styrene

Scheme 56. Dicarboxylation of alkenes with CO2 and formate as carbon sources

Scheme 57. Visible-light-driven selective dicarboxylation and tricarboxylation of allyl alcohol

Scheme 58. Visible-light-driven hydrocarboxylation and dicarboxyylation of inactive alkene

Scheme 59. Visible light-driven 1,3-dicarboxylate reaction of inactive alkene

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基于自由基机理光催化羧基化反应研究进展

Recent Advances in Photocatalytic Carboxylation Based on Free Radical Process

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