光化学转化二氧化碳合成羧酸化合物的研究进展

doi:10.6023/cjoc202405004

摘要/Abstract

光化学反应以洁净、节能、节约为目标, 为合成化学提供了新途径和新方法, 成为现代有机合成化学中非常活跃的研究领域之一. 二氧化碳(CO₂)由于其无毒、廉价易得、储量丰富且可循环再生等特点, 是合成化学中理想的C1合成子. 近年来, 光催化促进的CO₂向羧酸化合物的转化得到了快速发展, 为羧酸化合物的制备提供了一种温和并高效合成方法. 综述了光催化转化CO₂合成羧酸化合物的合成方法研究进展, 并对其部分反应机理做了相应的阐述.

关键词: 二氧化碳, 光催化, 羧基化

The pursuit of cleanliness, energy efficiency, and resource preservation through photochemical reactions has led to the emergence of novel pathways and methodologies in synthetic chemistry, rendering it one of the most dynamic research domains within modern organic synthesis. Carbon dioxide (CO₂), owing to its non-toxic, cost-effective, abundant, and recyclable attributes, serves as an optimal C1 precursor in synthetic chemistry. Recent years have witnessed rapid advancements in the photochemical conversion of CO₂ into carboxylic acid compounds, offering a gentle and highly efficient synthetic approach for their production. An overview of the research progress on the synthesis methodologies of carboxylic acid compounds through photochemical CO₂ conversion is provided, while certain associated reaction mechanisms are also elucidated.

Key words: carbon dioxide, photocatalysis, carboxylation

引用此文

袁盼锋, 朱灿明, 孟庆元. 光化学转化二氧化碳合成羧酸化合物的研究进展[J]. 有机化学, 2024, 44(10): 2997-3042.

Panfeng Yuan, Canming Zhu, Qingyuan Meng. Advances in the Synthesis of Carboxylic Acid by Photochemical Conversion of CO₂[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 2997-3042.

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图/表 67

Scheme 1. Visible-light-driven carboxylation of aryl halides by the combined use of palladium and photoredox catalysts[6]

Scheme 2. Carboxylation of aromatic and aliphatic bromides and triflates with CO2 by dual visible-light-nickel catalysis[7]

Scheme 3. Visible-light-driven carboxylation of benzyl bromides with CO2[8]

Scheme 4. Photoredox/Pd catalyzed C—F bonds carboxylation of gem-difluoroalkenes[9]

Scheme 5. Carboxylation of C—F bonds with CO2 via visible-light photoredox catalysis[10]

Scheme 6. Visible‐light photoredox‐catalyzed selective carboxylation of aryl C—F bonds with CO2[11]

Scheme 7. Visible-light-driven external-reductant-free carboxylation of tetra-alkyl ammonium salts[12]

Scheme 8. Carboxylation of C—N bons in cyclic amines with CO2 via visible-light photoredox catalysis[13]

Scheme 9. Carboxylation of aryl and alkenyl triflates via Pd and photoredox catalysts

Scheme 10. Visible-light photoredox-catalyzed carboxylation of activated C(sp3)—O bonds with CO2[15]

Scheme 11. Carboxylation of allylic alcohols via photoredox/nickel dual catalysis[16]

Scheme 12. Photocatalytic cross-electrophile coupling of free alcohols and CO2[17]

Scheme 13. Carboxylation of aryl epoxides by visible-light photoredox catalysis[18]

Scheme 14. Photocatalyst-free carboxylation of acylsilanes with CO2[19]

Scheme 15. UV light-driven carboxylation of benzylic C—H bonds in o-alkylphenyl ketones with CO2[21]

Scheme 16. Carboxylation of cyclohexene with CO2 in the presence with a ketone and a Cu complex under UV light[22]

Scheme 17. UV-light-induced carboxylation of C(sp3)—H bonds in benzyl amines[23]

Scheme 18. Visible light-driven direct carboxylation of benzylic CH bond with CO2 under metal-free conditions[24]

Scheme 19. UV-light-induced carboxylation of benzylic and aliphatic C—H bonds with CO2[25]

Scheme 20. Visible light-driven remote C(sp3)—H carboxylation[26]

Scheme 21. Visible-light-induced remote difunctionalizing carboxylation of unactivated alkenes[27]

Scheme 22. Photocatalytic C—H carboxylation of arenes and styrenes[28]

Scheme 23. Visible-light-driven thiolate-catalyzed carboxylation of C(sp2)—H bonds in N-heteroarenes[29]

Scheme 24. Dual Rh and photoredox-catalyzed hydrocarboxylation of alkenes with CO2[36]

Scheme 25. Selective β-carboxylation of styrenes with CO2 in continuous-flow reactors[37]

Scheme 26. Ligand-controlled regioselective hydrocarboxylation of alkenes with CO2

Scheme 27. Proposed mechanism of hydrocarboxylation with styrenes with CO2[38]

Scheme 28. Dual Ni/NiO and photoredox-catalyzed hydrocarboxylation of alkenes with CO2[39]

Scheme 29. Anti-Markovnikov hydrocarboxylation of alkenes with CO2 under external photocatalysis-free consitions[40]

Scheme 30. Photocatalytic di- and hydrocarboxylation of unactivated alkenes with CO2[41]

Scheme 31. Photocatalytic intermolecular dicarbofunctionalization of styrenes with CO2[42]

Scheme 32. Visible-light-mediated and iron-promoted thiocarboxylation of alkenes[43]

Scheme 33. Silacarboxylation and carbocarboxylation of styrenes and acrylates[44]

Scheme 34. Phosphonocarboxylation of alkenes with CO2

Scheme 35. Iodocarboxylation of activated alkenes with CO2 and lithium iodide

Scheme 36. Photoredox-catalyzed approach for the synthesis of γ-amino acids

Scheme 37. Photoredox-catalyzed dicarbofunctionalization of styrenes with amines

Scheme 38. External-photocatalyst-free alkyl-carboxylation of alkenes with CO2[49]

Scheme 39. Visible light-driven reductive arylcarboxylation of styrenes with CO2 and aryl halides[50]

Scheme 40. Photoredox catalyzed carbocarboxylation of activated alkenes via recycling CO2[51]

Scheme 41. Visible light-catalyzed carbocarboxylation of alkenes with sodium glycinate and CO2

Scheme 42. Photoredox-catalyzed formyl/carboxylation of alkenes with glyoxylic acid acetals and CO2

Scheme 43. Visible-light-mediated thiocarboxylation of alkenes

Scheme 44. Intramolecular arylcarboxylation of unactivated alkenes with CO2 under photoredox neutral conditions[55]

Scheme 45. Metallaphotoredox-enabled aminocarboxylation of alkenes with CO2

Scheme 46. Proposed catalytic cycle for aminocarboxylation of alkenes with CO2[56]

Scheme 47. Catalytic asymmetric cyanocarboxylation of styrenes[57]

Scheme 48. Reductive dicarboxylation of alkenes, allenes, and (hetero)arenes with CO2

Scheme 49. Proposed mechanism for reductive decarboxylation[58]

Scheme 50. Photocatalytic dicarboxylation of alkenes with CO2 and formate[59]

Scheme 51. Photocatalytic divergent di- or tricarboxylation of allylic alcohols with CO2[60]

Scheme 52. Visible-light-driven alkene dicarboxylation with formate and CO2

Scheme 53. Photocatalyzed hydrocarboxylation of alkynes

Scheme 54. Photocatalyzed heterocycle syntheses through alkyne carboxylation

Scheme 55. Visible light-mediated dearomative difunctionalization of indoles[63]

Scheme 56. Dearomative arylcarboxylation of nonactivated arenes with CO2

Scheme 57. Photo‐catalyzed dearomatization for the synthesis spirocyclic carboxylic acids

Scheme 58. Intermolecular dearomative carboxylation of indoles and heteroanalogues

Scheme 59. Visible light-mediated catalytic hydrocarboxylation of ketimines using CO2

Scheme 60. Reductive hydrocaroxylation of ketimines under light irradiation[69]

Scheme 61. Visible-light-catalyzed umpolung carboxylation of carbonyl compounds with CO2

Scheme 62. Visible light-catalyzed umpolung carboxylation of carbonyl compounds using DMBI as reductant

Scheme 63. Carboxylation of cyclic oxime esters with CO2 via visible light catalysis[73]

Scheme 64. 1,3‐Dicarboxylation of unactivated alkenes with CO2 via 1,2‐aryl migration[74]

Scheme 65. Carboxylation of alkenes with CO2 via photocatalytic cleavage of C=C double bonds

Scheme 66. Proposed mechanism for the deconstructive carboxylation of C=C double bonds[76]

Scheme 67. Visible-light mediated carboxylation via C=C double bond cleavage

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