可见光诱导分子氧参与烯烃氧化双官能化反应研究进展

doi:10.6023/cjoc202506019

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3495-3516.DOI: 10.6023/cjoc202506019 上一篇下一篇

综述与进展

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)

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摘要/Abstract

分子氧因具有含量丰富、价格低廉和无污染的优点被认为是一种理想的氧化剂. 但是, 氧气在室温下参与反应通常具有速率慢及选择性低等缺点, 一般需借助生物酶、金属催化剂或其他条件来促进转化. 可见光诱导的有机反应具有操作步骤简洁、绿色可持续以及反应条件温和等优势, 受到了化学研究者的广泛关注. 近年来, 可见光诱导分子氧参与的烯烃氧化双官能化反应得到了迅速的发展, 已成为有机合成化学领域的研究热点之一. 总结了近年来可见光催化氧气参与的烯烃氧化官能化反应合成相应含氧化合物的研究进展, 对反应普适性和相应的反应机理进行了重点描述, 并对该领域的发展方向进行了展望.

关键词: 可见光, 分子氧, 烯烃, 含氧化合物

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

引用此文

王雷雷, 候亚楠, 丁虹雨, 吴娟娟, 王祖利, 魏伟, 易东. 可见光诱导分子氧参与烯烃氧化双官能化反应研究进展[J]. 有机化学, 2025, 45(10): 3495-3516.

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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图/表 53

图式1. 可见光诱导分子氧参与烯烃氧化双官能化反应

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

图式2. 光诱导芳基烯烃与氧气和芳基重氮盐氧化芳基化反应

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

图式3. 光诱导芳基烯烃与芳基重氮盐和氧气氧芳基化反应机理

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

图式4. 光诱导抗坏血酸催化烯烃与芳基重氮盐和氧气的氧化芳基化反应

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

图式5. 可见光诱导抗坏血酸催化氧芳基化反应机理

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

图式6. 光诱导烯烃与碘代1,1,1-三氟乙烷和氧气的双官能化反应

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

图式7. 光诱导烯烃与碘代1,1,1-三氟乙烷和氧气的双官能化反应机理

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

图式8. 光诱导芳烯与氧气反应生成4-芳基四氢萘醌

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

图式9. 光诱导芳烯与氧气反应生成4-芳基四氢萘醌的可能机理

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

图式10. 光诱导烯烃与芳基肼和氧气的氧化反应

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

图式11. 光诱导烯烃与芳基肼的需氧氧化反应机理

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

图式12. 光诱导烯烃与碘代全氟烷烃和氧气的羟基全氟烷基化反应

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

图式13. 光诱导烯烃与三氟甲基亚磺酸钠和氧气进行氧化三氟甲基化反应

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

图式14. 光诱导铜催化烯烃与丙二酸酯和氧气进行氧化烷基化反应

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

图式15. 光诱导重氮盐、丙烯腈、氧气和醇氧化反应合成α-芳基酯

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

图式16. 光诱导重氮盐、丙烯腈、氧气和醇氧化反应合成α-芳基酯的可能机理

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

图式17. 光诱导分子内烯基羧酸需氧氧化反应

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

图式18. 光诱导烯烃与羧酸和氧气的双氧化反应

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

图式19. 烯烃与羧酸和氧气双氧化反应机理

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

图式20. 光诱导芳香烯烃与分子氧和N-羟基邻苯二甲酰亚胺双氧化反应

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

图式21. 光诱导烯烃与氧气和NHPI双氧化反应可能机理

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

图式22. 光诱导吲哚与分子氧氧化合成4-喹啉酮

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

图式23. 光诱导吲哚与分子氧氧化双官能化反应可能机理

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

图式24. 光诱导烯烃与三甲基硅基叠氮和氧气的氧化叠氮化反应合成β-叠氮醇

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

图式25. 光诱导烯烃氧化叠氮化反应合成β-叠氮醇机理

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

图式26. 光诱导铜催化烯烃氧化叠氮化反应合成α-叠氮酮

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

图式27. 光诱导铜催化烯烃氧化叠氮化反应机理

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

图式28. 光诱导玫瑰红B和PhSeSePh共催化烯烃与氧气和TMSN3氧化叠氮化合成α-叠氮酮

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

图式29. 光诱导玫瑰红B和PhSeSePh共催化烯烃与氧气和TMSN3氧化叠氮化机理

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

图式30. 光诱导氧气氧化官能化N-芳基甘氨酸与烯烃

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

图式31. 光诱导N-芳基甘氨酸与烯烃氧化官能化反应机理

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

图式32. 光诱导α-甲基芳香烯烃与氧气和苯并三唑氧化胺化反应

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

图式33. 光诱导α-甲基芳香烯烃与氧气和苯并三唑氧化胺化反应机理

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

图式34. 光诱导eosin Y催化烯烃与硫酚和氧气氧化合成β-羰基亚砜

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

图式35. 光诱导烯烃与硫氰酸铵和氧气氧化环合反应合成5-芳基-2-亚氨基-1,3-氧硫杂环戊烷

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

图式36. 光诱导烯烃氧化环化合成5-芳基-2-亚氨基-1,3-氧硫杂环戊烷反应机理

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

图式37. 光诱导烯烃与二硫化碳氧化合成1,3-氧硫杂环戊烷- 2-硫酮

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

图式38. 光诱导芳基联烯选择性氧化合成α,β-不饱和醛/酮

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

图式39. 光诱导孟加拉玫红B催化烯烃与硫醇和氧气进行亚砜化反应

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

图式40. 光诱导烯烃与氧气和磺酰肼氧砜化反应合成β-羰基/羟基砜

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

图式41. 光诱导烯烃与亚磺酸和氧气氧砜化反应合成β-羰基砜

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

图式42. 光诱导烯烃与亚磺酸和氧气氧砜化反应机理

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

图式43. 光诱导烯烃与氧气、胺和CS2的双官能化反应

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

图式44. 光诱导烯烃与氧气、胺和CS2的双官能化反应

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

图式45. 光诱导芳基烯烃与杂芳基硫醇和氧气双官能化反应制备β-羟基硫醚

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

图式46. 光诱导芳基烯烃与杂芳基硫醇和氧气双官能化反应机理

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

图式47. 光催化烯烃与硫代羧酸和氧气氧化硫酯化反应

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

图式48. 光催化肉桂酸与二芳基氧膦脱羧氧膦反应合成β-羰基氧膦

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

图式49. 光介导肉桂酸与二芳基氧膦的氧膦化反应机理

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

图式50. 光催化烯烃与二芳基氧膦和氧气氧膦反应合成β-羰基氧膦

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

图式51. 光催化烯烃与二芳基膦氧和氧气氧膦化反应机理

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

图式52. 光诱导铁催化烯烃与二芳基氧膦和氧气氧膦反应合成β-羰基氧膦

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

图式53. 光诱导铁催化烯烃与二芳基氧膦和氧气氧膦反应机理

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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