Research Progress on Visible Light-Induced Oxidative Difun-ctionalization of Olefins with Molecular Oxygen

doi:10.6023/cjoc202506019

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3495-3516.DOI: 10.6023/cjoc202506019 Previous Articles Next Articles

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可见光诱导分子氧参与烯烃氧化双官能化反应研究进展

王雷雷^a, 候亚楠^b, 丁虹雨^b, 吴娟娟^a^,^*(), 王祖利^d, 魏伟^b^,^*(), 易东^c^,^*()

^a 德州学院药学院新型药物辅料与缓控释制剂山东省工程研究中心山东德州 253023
^b 曲阜师范大学化学与化工学院山东曲阜 273165
^c 西南医科大学药学院四川泸州 646000
^d 南京林业大学林木生物质低碳高效利用国家工程研究中心南京 210037

收稿日期:2025-06-13 修回日期:2025-07-15 发布日期:2025-08-18
基金资助:
山东省自然科学基金(ZR2024QB405); 德州学院基金(2023xjrc203); 德州学院基金(2024xjrc123); 及泸州市人民政府西南医科大学科技战略合作(2023LZXNYDJ019)

Research Progress on Visible Light-Induced Oxidative Difun-ctionalization of Olefins with Molecular Oxygen

Leilei Wang^a, Ya'nan Hou^b, Hongyu Ding^b, Juanjuan Wu^a^,^*(), Zuli Wang^d, Wei Wei^b^,^*(), Dong Yi^c^,^*()

^a Shandong Provincial Engineering Research Center of Novel Pharmaceutical Excipients and Controlled Release Preparations, College of Pharmacy, Dezhou University, Dezhou, Shandong 253023
^b School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
^c School of Pharmacy, Southwest Medical University, Luzhou, Sichuan 646000
^d National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037

Received:2025-06-13 Revised:2025-07-15 Published:2025-08-18
Contact: * wjjll_1@163.com; weiweiqfnu@163.com; yidong@swmu.edu.cn
Supported by:
Natural Science Foundation of Shandong Province(ZR2024QB405); Research Project Fund of Dezhou University(2023xjrc203); Research Project Fund of Dezhou University(2024xjrc123); Science and Technology Strategic Cooperation Programs of Luzhou Municipal People's Government and Southwest Medical University(2023LZXNYDJ019)

Molecular oxygen is regarded as an ideal oxidant due to its abundant content, low cost and non-polluting nature. However, reactions involving dioxygen at room temperature usually suffer from slow rates and low selectivity, and thus require the assistance of enzymes, metal catalysts or other conditions to promote transformation. Visible light-induced organic reactions have attracted extensive attention from chemical researchers due to their simple operation steps, green and sustainable nature as well as mild reaction conditions. In recent years, visible light-induced oxidation difunctionalizations of olefins with molecular oxygen have witnessed swift advancement and became one of the research hotspots in the field of organic synthesis. The recent research progress in the synthesis of oxygen-containing compounds through visible light-catalyzed oxidative difunctionalizations of alkenes with dioxygen is summarized. The selected examples of substrates and the corresponding reaction mechanisms are described, and the development of this field are also prospected.

Key words: visible light, molecular oxygen, olefin, oxygen-containing compound

Cite this article

Leilei Wang, Ya'nan Hou, Hongyu Ding, Juanjuan Wu, Zuli Wang, Wei Wei, Dong Yi. Research Progress on Visible Light-Induced Oxidative Difun-ctionalization of Olefins with Molecular Oxygen[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3495-3516.

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Fig. & Tab. 53

Scheme 1. Visible light-induced oxidative difunctionalization of olefins with molecular oxygen

Scheme 2. Visible light-induced oxo-arylation of aromatic alkenes with dioxygen and aryl diazonium salts

Scheme 3. Mechanism of light-induced oxo-arylation of arylalkenes with aryl diazonium salts and dioxygen

Scheme 4. Visible light-induced ascorbic acid catalyzed oxo- arylation reaction of alkenes with aryl diazonium salts and dioxygen

Scheme 5. Mechanism of visible light-induced ascorbic acid catalyzed oxo-arylation reaction

Scheme 6. Visible light-induced difunctionalization reactions of alkenes with 1,1,1-trifluoro-2-iodoethane and dioxygen

Scheme 7. Possible mechanism of visible light-induced difunctionalization reactions of alkenes with 1,1,1-trifluoro-2-iodo- ethane and dioxygen

Scheme 8. Visible light-induced the reaction of aromatic alkenes with dioxygen to access 4-aryl tetrahydronaphthalene quinones

Scheme 9. Possible mechanism of light-induced the reaction of aromatic alkenes with dioxygen to access 4-aryl tetrahydronaphthalene quinones

Scheme 10. Visible light-induced aerobic oxidation of alkenes with arylhydrazines and dioxygen

Scheme 11. Reaction mechanism of visible light-induced aerobic oxidation of alkenes with arylhydrazines and dioxygen

Scheme 12. Visible light-induced hydroxylperfluoroalkylation of alkenes with perfluoroalkyl iodide and dioxygen

Scheme 13. Visible-light-induced oxidative trifluoromethylation of alkenes with CF3SO2Na and dioxygen

Scheme 14. Visible light-induced Cu-catalyzed oxoalkylation of alkenes with malonates and dioxygen

Scheme 15. Visible light-induced the oxidation reaction of diazonium salts, acrylonitrile, oxygen and alcohols to synthesize α-arylated esters

Scheme 16. Mechanism of visible light induced the oxidation reaction of diazonium salts, acrylonitrile, oxygen and alcohols to synthesize α-arylated esters

Scheme 17. Visible light-induced aerobic oxidation reaction of intramolecular enoyl carboxylic acids

Scheme 18. Visible light-induced dioxynation of alkenes with carboxylic acid and molecular oxygen

Scheme 19. Mechanism of the dioxynation reaction of alkenes with carboxylic acids and oxygen

Scheme 20. Visible light-induced dioxynation of aromatic alkenes with molecular oxygen and N-hydroxyanisidine

Scheme 21. Possible mechanism of the light-induced dioxynation of alkenes with dioxygen and NHPI

Scheme 22. Visible light-induced oxidation reaction of indole with dioxygen leading to 4-quinoxalines

Scheme 23. Possible mechanism of the difunctionalization reaction of indole with molecular oxygen

Scheme 24. Visible light-induced oxyazidation of alkenes with trimethylsilyl azide and dioxygen to synthesize β-azide alcohols

Scheme 25. Mechanism of visible light-induced oxyazidation of alkenes to synthesize β-azide alcohol

Scheme 26. Visible light-induced copper catalyzed oxyazidation of alkenes to synthesize α-azidoketones.

Scheme 27. Mechanism of visible light-induced copper catalyzed oxyazidation of alkenes

Scheme 28. Visible-light-enabled Rose Bengal and PhSeSePh co-catalyzed oxyazidation of alkenes with TMSN3 and dioxygen leading to α-azidoketones

Scheme 29. Mechanism of visible-light-enabled Rose Bengal and PhSeSePh co-catalyzed oxyazidation of alkenes with TMSN3 and dioxygen

Scheme 30. Visible light-induced oxidative functionalization of N-arylglycine and olefin with dioxygen

Scheme 31. Possible mechanism of light induced oxidative functionalization of N-arylglycine with olefin

Scheme 32. Visible light-induced oxyamidation reaction of α-methylstyrene with dioxygen and benzotriazole

Scheme 33. Mechanism of visible light-induced oxyamidation reaction of α-methylstyrene with dioxygen and benzotriazole

Scheme 34. Visible light-induced eosin Y catalyzed oxidation of alkenes with dioxygen and thiols to form β-keto sulfoxides

Scheme 35. Visible light-induced oxidative cyclication of alkenes with NH4SCN and dioxygen for the synthesis of 5-aryl-2- imino-1,3-oxidosulfazacyclopentanes

Scheme 36. Possible mechanism of visible light induced oxidative cyclication of alkenes for the synthesis of 5-aryl-2-imino-1,3- oxidosulfazacyclopentane

Scheme 37. Visible light-induced oxidative cyclication of alkenes with dioxygen and CS2 for the synthesis of 1,3-oxathiaza- cyclopentane-2-thione

Scheme 38. Visible light-induced oxidation of allene for the synthesis of α,β-unsaturated aldehydes/ketones

Scheme 39. Visible light-induced Rose Bengal-catalyzed sulfoxidation of alkenes with thiols and molecular oxygen

Scheme 40. Visible light-induced oxysulfonylation of alkenes with dioxygen and sulfonylhydrazides leading to β-ketosulfones/ β-hydroxysulfones

Scheme 41. Visible light-induced oxysulfonylation of alkenes with dioxygen and sulfinic acids to access β-ketosulfones

Scheme 42. Mechanism of visible light-induced oxysulfonylation of alkenes with dioxygen and sulfinic acids

Scheme 43. Visible light-induced difunctionalization of alkenes with dioxygen, amines and CS2

Scheme 44. Mechanism of visible light-induced difunctionalization of alkenes with dioxygen, amines and CS2

Scheme 45. Visible light-induced difunctionalization of alkenes with heteroaryl thiols and dioxygen to access β-hydroxythioethers

Scheme 46. Mechanism of visible light-induced difunctionalization of alkenes with heteroaryl thiols and dioxygen

Scheme 47. Photocatalytic oxidative thioesterification of alkenes with thioic acids and dioxygen

Scheme 48. Photocatalytic decarboxylative oxyphosphorylation of cinnamic acids with diarylphosphine oxides to form β-ketophosphine oxide

Scheme 49. Mechanism of visible light-mediated oxyphosphorylation of cinnamic acids with diarylphosphine oxides

Scheme 50. Photocatalytic oxyphosphorylation of alkenes with diarylphosphine oxides and dioxygen to form β-ketophosphine oxides

Scheme 51. Mechanism of photocatalytic oxyphosphorylation of alkenes with diarylphosphine oxides and dioxygen

Scheme 52. Light-induced iron catalyzed oxyphosphorylation of alkenes with diarylphosphine oxides and dioxygen to form β-ketophosphine oxides

Scheme 53. Mechanism of light-induced iron catalyzed oxyphosphorylation of alkenes with diarylphosphine oxides and dioxygen

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可见光诱导分子氧参与烯烃氧化双官能化反应研究进展

Research Progress on Visible Light-Induced Oxidative Difun-ctionalization of Olefins with Molecular Oxygen

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