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

doi:10.6023/cjoc202506028

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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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