Photoinduced C—F Bond Cleavage α-Trifluoromethyl Alkenes for the Synthesis of gem-Difluoroalkenes

doi:10.6023/cjoc202512002

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (8): 3219-3226.DOI: 10.6023/cjoc202512002 Previous Articles Next Articles

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光诱导下三氟甲基烯烃C—F键断裂合成偕二氟烯烃

王彬^a, 叶波^b, 王磊^a^,^*(), 何红^a, 马永敏^a^,^*()

^a 台州学院高研院和药学院浙江台州 318000
^b 台州市生态环境局临海分局浙江台州 317000

收稿日期:2026-02-06 修回日期:2026-03-30 发布日期:2026-05-13
通讯作者: 王磊, 马永敏
基金资助:
国家自然科学基金(22471187)

Photoinduced C—F Bond Cleavage α-Trifluoromethyl Alkenes for the Synthesis of gem-Difluoroalkenes

Bin Wang^a, Bo Ye^b, Lei Wang^a^,^*(), Hong He^a, Yongmin Ma^a^,^*()

^a Advanced Research Institute & School of Pharmaceutical Sciences, Taizhou University, Taizhou, Zhejiang 318000
^b Linhai Branch of Taizhou Ecological Environment Bureau, Linhai, Taizhou, Zhejiang 317000

Received:2026-02-06 Revised:2026-03-30 Published:2026-05-13
Contact: Lei Wang, Yongmin Ma
Supported by:
National Natural Science Foundation of China(22471187)

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Abstract

A highly efficient photoinduced radical addition/defluoroalkylation of dihydroquinazolinones and CF₃-substituted alkenes was developed, affording a diverse set of gem-difluoroalkenes under mild visible-light conditions. This strategy relies on C—C bond cleavage of dihydroquinazolinones to generate alkyl radicals, followed by addition and β-fluoride elimination. This reaction exhibits broad substrate scope, excellent functional group tolerance, and operational simplicity.

Key words: gem-difluoroalkene, C—F bond cleavage, photochemistry, α-trifluoromethyl alkene

Cite this article

Bin Wang, Bo Ye, Lei Wang, Hong He, Yongmin Ma. Photoinduced C—F Bond Cleavage α-Trifluoromethyl Alkenes for the Synthesis of gem-Difluoroalkenes[J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 3219-3226.

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Entry	Variation from the optimal conditions	Yield^b/%
1	None	96
2	DMSO as solvent	90
3	MeCN as solvent	92
4	K₃PO₄ (1 equiv.) was added	89
5	Na₂CO₃ (1 equiv.) was added	90
6	NaOAc (1 equiv.) was added	90
7	KHCO₃ (1 equiv.) was added	85
8	Under air atmosphere	81
9	Under O₂ atmosphere	62
10	Without photocatalyst	0
11	Without light	0

Entry	Variation from the optimal conditions	Yield^b/%
1	None	96
2	DMSO as solvent	90
3	MeCN as solvent	92
4	K₃PO₄ (1 equiv.) was added	89
5	Na₂CO₃ (1 equiv.) was added	90
6	NaOAc (1 equiv.) was added	90
7	KHCO₃ (1 equiv.) was added	85
8	Under air atmosphere	81
9	Under O₂ atmosphere	62
10	Without photocatalyst	0
11	Without light	0

光诱导下三氟甲基烯烃C—F键断裂合成偕二氟烯烃

Photoinduced C—F Bond Cleavage α-Trifluoromethyl Alkenes for the Synthesis of gem-Difluoroalkenes

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Fig. & Tab. 5

References 16

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