光诱导下三氟甲基烯烃C—F键断裂合成偕二氟烯烃

doi:10.6023/cjoc202512002

有机化学 ›› 2026, Vol. 46 ›› Issue (8): 3219-3226.DOI: 10.6023/cjoc202512002 上一篇下一篇

研究论文

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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摘要/Abstract

发展了一种温和的可见光条件下的高效光诱导二氢喹唑啉酮和三氟甲基烯烃的自由基加成/脱氟烷基化反应, 得到多种偕二氟烯烃化合物. 该方法依靠二氢喹唑啉酮的C—C键断裂生成烷基自由基, 然后与三氟甲基烯烃进行加成/β-氟消除. 该反应具有底物范围广泛、官能团耐受性好和操作简单等优点.

关键词: 偕二氟烯烃, C—F键断裂, 光化学, α-三氟甲基烯烃

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

引用此文

王彬, 叶波, 王磊, 何红, 马永敏. 光诱导下三氟甲基烯烃C—F键断裂合成偕二氟烯烃[J]. 有机化学, 2026, 46(8): 3219-3226.

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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