基于自由基机理光催化羧基化反应研究进展

doi:10.6023/cjoc202405041

有机化学 ›› 2024, Vol. 44 ›› Issue (10): 2961-2996.DOI: 10.6023/cjoc202405041 上一篇下一篇

综述与进展

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
通讯作者: 张雷, 莫凡洋
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: Lei Zhang, Fanyang Mo
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)

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摘要/Abstract

二氧化碳(CO₂)是一种对气候变化有重要影响的温室气体. 从化学角度考虑, 作为“碳一(C1)”资源, CO₂具有储量丰富、廉价易得及无毒可再生等特点. 通过化学转化的方式将CO₂资源化利用, 并用于合成高附加值化学品, 是服务国家重大战略需求的重要方式, 也是响应国家2030年“碳达峰”与2060年“碳中和”目标的重要举措. 有机光催化能够利用光能激发电子转移, 引发化学键的断裂和重组, 促进反应的进行, 具备条件温和、绿色清洁以及选择性高等优点. CO₂资源化利用与有机光催化相结合所形成的光催化羧基化反应体系, 能够为羧基化反应的研究提供新思路. 系统阐述了两种光催化羧基化反应, 即以碳负离子为关键中间体和以CO₂自由基负离子为关键中间体的羧基化反应.

关键词: 光催化, 二氧化碳(CO₂), 羧基化反应, 碳负离子, CO₂自由基负离子

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

引用此文

李文珂, 孙北奇, 张雷, 莫凡洋. 基于自由基机理光催化羧基化反应研究进展[J]. 有机化学, 2024, 44(10): 2961-2996.

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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图/表 59

图式1. 光催化芳基烯烃双官能团化反应

Scheme 1. Photocatalytic difunctionalization of aryl alkenes

图式2. 可见光催化烯烃的硅羧基化和碳羧基化反应

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

图式3. 可见光催化CO2参与的活化烯烃膦酰羧基化反应

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

图式4. 可见光催化芳基卤化物和CO2参与的苯乙烯碳羧基化反应

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

图式5. 利用胺和CO2实现的可见光催化活化烯烃的双官能团化反应

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

图式6. 氨基酸对烯烃的双官能团修饰

Scheme 6. Bifunctional modification of alkenes by amino acids

图式7. 可见光催化肟酯、活化烯烃和CO2三组分羧化反应

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

图式8. 可见光驱动无需外加光催化剂的CO2参与的烯烃的烷基羧化反应

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

图式9. 可见光催化CO2和芳基碘化物参与的烯酰胺的芳基羧基化反应

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

图式10. 可见光催化CO2参与基于1,5-氢迁移过程的远程C(sp3)—H键羧基化反应

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

图式11. 可见光催化CO2参与活化烯烃的裂解羧化反应

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

图式12. 可见光驱动通过碳碳双键断裂过程的利用CO2的烯烃羧化反应

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

图式13. 可见光驱动的1,3-二烯的羧基化反应

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

图式14. CO2参与的可见光催化苄位C(sp3)—H的直接羧化反应

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

图式15. 可见光催化CO2参与的远端C(sp3)—H键羧基化反应

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

图式16. 可见光催化CO2参与的张力环C—C键双羧基化反应

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

图式17. 可见光催化基于1,5-氢迁移机理的苄位C(sp3)—H键羧化反应

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

图式18. CO2参与的以烯酰胺、烯酰亚胺为底物的可见光催化羧化反应

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

图式19. 芳基亚胺为底物的可见光催化CO2参与的羧化反应

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

图式20. 可见光催化CO2参与环酮肟酯羧化反应

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

图式21. 可见光催化下CO2参与的季铵盐C—N键羧基化反应

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

图式22. 可见光催化CO2参与环胺C—N键羧基化反应

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

图式23. 可见光催化CO2参与苄基卤化物的羧基化反应

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

图式24. 可见光催化CO2参与的苯甲基溴化物羧化反应

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

图式25. 可见光催化CO2参与的苯甲基氯化物羧化反应

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

图式26. 可见光催化CO2参与烷基C—F键羧基化反应

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

图式27. 可见光催化CO2参与的多氟芳烃的选择性C—F键羧基化反应

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

图式28. 可见光催化CO2参与酰基硅烷的羧基化反应

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

图式29. 可见光催化CO2参与羰基化合物的羧基化反应

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

图式30. 可见光催化CO2参与芳香醛或酮的羧基化反应

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

图式31. 可见光催化CO2参与的C(sp3)—O键羧基化反应

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

图式32. 可见光催化CO2参与的苄醇C(sp3)—O键羧基化反应

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

图式33. 可见光催化CO2参与的芳基环氧化合物羧基化反应

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

图式34. 可见光催化CO2参与的吲哚还原性去芳构化芳基羧基化反应

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

图式35. 可见光催化的非活化芳烃底物的还原去芳构化羧基化反应

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

图式36. 可见光催化CO2参与的苄基邻卤芳醚的连续去芳构化/羧化反应

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

图式37. 可见光催化CO2参与的吲哚的脱芳构化羧化反应

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

图式38. 可见光催化CO2参与的吲哚分子间的α-氨甲基/羧基化脱芳构化反应

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

图式39. 紫外光条件下CO2•-参与苯乙烯衍生物的反马氏羧化反应

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

图式40. 紫外光条件下CO2•-参与胺的羧化反应

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

图式41. 可见光驱动铁促进CO2参与的烯烃与苯硫酚的硫羧基化反应

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

图式42. 紫外光驱动活化烯烃碘羧化反应

Scheme 42. Photoiodocarboxylation of activated alkenes

图式43. 可见光驱动无金属催化剂的基于CO2•-烯烃羧化反应

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

图式44. 可见光驱动无金属催化剂基于$\mathrm{CO}_{2}^{-\cdot}$炔烃羧化反应

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

图式45. 可见光催化CO2参与非活化烯烃的芳基羧基化反应

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

图式46. 可见光催化动基于CO2•-烯烃的羧化反应

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

图式47. 可见光和加热条件甲酸盐为碳源的烯烃羧化反应

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

图式48. 可见光催化甲酸盐为碳源实现活化烯烃的氢羧化反应

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

图式49. 可见光催化甲酸盐参与的非活化烯烃的氢羧化反应

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

图式50. 可见光促进甲酸盐为碳源合成α-氨基酸衍生物

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

图式51. 可见光照射加热条件下杂环芳香族化合物的去芳构化羧化反应

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

图式52. 缺电子烯烃光催化偶联反应

Scheme 52. Photocatalytic coupling reaction of electron-deficient olefin

图式53. 在空气中利用甲酸盐进行烯烃的羧化反应

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

图式54. 利用甲酸盐作为还原剂和碳源的光催化脱氟羧基化反应

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

图式55. 可见光催化α-三氟甲基苯乙烯的脱氟羧基化反应

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

图式56. CO2和甲酸盐作共同羧基来源对烯烃的双羧基化反应

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

图式57. 可见光催化烯丙醇选择性双羧基化和三羧基化反应

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

图式58. 可见光催化非活化烯烃的氢羧基化和双羧基化反应

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

图式59. 可见光催化非活化烯烃的1,3-二羧基化反应

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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