Visible Light-Promoted Oxidative Cleavage of Alkene Using an Organic Photocatalyst

doi:10.6023/cjoc202506028

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 633-640.DOI: 10.6023/cjoc202506028 Previous Articles Next Articles

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可见光促进有机染料催化烯烃的氧化裂解反应

李文静^*(), 沈思语, 梁玲玲, 张雪娇, 苗延青, 尤静

西安医学院药学院西安 710021

收稿日期:2025-09-09 修回日期:2025-09-22 发布日期:2025-10-09
通讯作者: 李文静
基金资助:
陕西省科技厅(2025JC-YBQN-136); 陕西省科技厅(2025JC-YBMS-178); 陕西省教育厅(24JK0646); 西安医学院(2023BS30); 西安医学院(2022NLTS078); 西安医学院(2024NLTS133)

Visible Light-Promoted Oxidative Cleavage of Alkene Using an Organic Photocatalyst

Wenjing Li^*(), Siyu Shen, Lingling Liang, Xuejiao Zhang, Yanqing Miao, Jing You

School of Pharmacy, Xi'an Medical University, Xi'an 710021

Received:2025-09-09 Revised:2025-09-22 Published:2025-10-09
Contact: Wenjing Li
Supported by:
Foundation of Shaanxi Provincial Science and Technology Department(2025JC-YBQN-136); Foundation of Shaanxi Provincial Science and Technology Department(2025JC-YBMS-178); Shaanxi Provincial Department of Education(24JK0646); Xi'an Medical University(2023BS30); Xi'an Medical University(2022NLTS078); Xi'an Medical University(2024NLTS133)

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Abstract

A visible-light-promoted method for the selective oxidation and cleavage of alkene C=C bonds to afford various aromatic ketones is reported by using Na₂-Eosin Y as photocatalyst and oxygen as oxidant. This catalytic system presents excellent reaction performance, and only 1 mol% catalyst is required to achieve the conversion under mild conditions. Additionally, this protocol shows a broad substrate scope and good functional group tolerance. Moreover, the synthetic application value of this method was verified by a gram-scale experiment, and ketoprofen methyl ester and fenofibrate with medicinal value were successfully prepared with high yield. Mechanistic studies investigated the effects of superoxide radical anion on the reaction and a possible reaction mechanism was proposed accordingly.

Key words: visible-light, Na₂-Eosin Y, alkene, oxidative cleavage, aromatic ketones

Cite this article

Wenjing Li, Siyu Shen, Lingling Liang, Xuejiao Zhang, Yanqing Miao, Jing You. Visible Light-Promoted Oxidative Cleavage of Alkene Using an Organic Photocatalyst[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 633-640.

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Fig. & Tab. 8

References 21

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Entry	Quencher	Species Tested	Yield^b
1	TEMPO	Radical	Trace
2	BHT	Radical	Trace
3	DPPH	Superoxide radical anion	Trace
4	Benzoquinone	Superoxide radical anion	NR
5	DABCO	—	75%
6	NaN₃	—	81%

Entry	Quencher	Species Tested	Yield^b
1	TEMPO	Radical	Trace
2	BHT	Radical	Trace
3	DPPH	Superoxide radical anion	Trace
4	Benzoquinone	Superoxide radical anion	NR
5	DABCO	—	75%
6	NaN₃	—	81%

可见光促进有机染料催化烯烃的氧化裂解反应

Visible Light-Promoted Oxidative Cleavage of Alkene Using an Organic Photocatalyst

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References 21

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Entry	Photocatalyst	Solvent	Yield^b/%
1	4,5-Dibromofluorescein	MeOH	25
2	Fluorescein	MeOH	29
3	Eosin Y	MeOH	38
4	Rhodamine B	MeOH	27
5	Eosin YS	MeOH	24
6	Eosin B	MeOH	31
7	Na₂-Eosin Y	MeOH	69
8	Rose bengal	MeOH	22
9	Neutral red	MeOH	27
10	Mes-Acr^＋$\mathrm{ClO}_{4}^{-}$	MeOH	56
11	Na₂-Eosin Y	CH₃CN	59
12	Na₂-Eosin Y	DCE	55
13	Na₂-Eosin Y	Acetone	52
14	Na₂-Eosin Y	THF	47
15	Na₂-Eosin Y	1,4-Dioxane	54
16	Na₂-Eosin Y	EtOH	63
17	Na₂-Eosin Y	DMF	54
18	Na₂-Eosin Y	Toluene	46
19^c	Na₂-Eosin Y	MeOH	88

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