Visible-Light-Driven Tertiary Amine-Promoted Acylfluoroalkylation of Alkenes

doi:10.6023/cjoc202602019

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3737-3747.DOI: 10.6023/cjoc202602019 Previous Articles Next Articles

ARTICLE

可见光诱导叔胺促进的烯烃酰基氟烷基化反应

曾添晴^a, 倪宇阳^a, 袁瑶^a^,^*(), 朱钢国^a^,^b^,^*()

^a 浙江师范大学化学与材料科学学院先进催化材料教育部重点实验室浙江金华 321004
^b 金华职业技术大学制药工程学院 321017 浙江金华浙江金华 321004

收稿日期:2026-02-23 修回日期:2026-04-04 发布日期:2026-05-07
通讯作者: 袁瑶, 朱钢国
基金资助:
国家自然科学基金(22071218)

Visible-Light-Driven Tertiary Amine-Promoted Acylfluoroalkylation of Alkenes

Tianqing Zeng^a, Yuyang Ni^a, Yao Yuan^a^,^*(), Gangguo Zhu^a^,^b^,^*()

^a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang 321004
^b College of Pharmaceutical Engineering, Jinhua University of Vocational Technology, Jinhua, Zhejiang 321017

Received:2026-02-23 Revised:2026-04-04 Published:2026-05-07
Contact: Yao Yuan, Gangguo Zhu
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
Supported by:
National Natural Science Foundation of China(22071218)

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Abstract

A visible light-driven amine cation radical-mediated hydrogen atom transfer strategy was reported, successfully achieving the fluoroalkylation cyclization reaction of alkenal with bromodifluoroacetate. This method achieves the direct conversion of aldehydes to ketones under mild conditions by forming an electron donor-acceptor (EDA) complex in situ, and constructs fluorinated cyclic ketones. The reaction exhibits excellent functional group compatibility, broad substrate applicability, and good yield. Mechanistic studies indicate that the amine cation radical can rapidly abstract hydrogen atoms from the α-car- bon of alkoxy radicals, effectively avoiding the competitive 1,5-hydrogen atom transfer (HAT) side reaction.

Key words: amine radical cations, hydrogen atom transfer (HAT), aldehyde-to-ketone transformation, radical reaction

Cite this article

Tianqing Zeng, Yuyang Ni, Yao Yuan, Gangguo Zhu. Visible-Light-Driven Tertiary Amine-Promoted Acylfluoroalkylation of Alkenes[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3737-3747.

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References 11

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Entry	Amine	λ/nm	Solvent	Yield^b/%
1	TEEDA	450~460	DMA	23
2	Et₃N	450~460	DMA	20
3	TMEDA	450~460	DMA	80
4	DABCO	450~460	DMA	87
5	DBU	450~460	DMA	0
6	DABCO	456	DMA	81
7	DABCO	440	DMA	84
8	DABCO	390	DMA	92 (80)^c
9	DABCO	370	DMA	90
10	DABCO	390	DMF	90
11	DABCO	390	DMSO	85
12	DABCO	390	MeCN	46
13	DABCO	390	DCM	88
14	DABCO	390	MeOH	10
15	—	390	DMA	0
16	DABCO	—	DMA	0

Entry	Amine	λ/nm	Solvent	Yield^b/%
1	TEEDA	450~460	DMA	23
2	Et₃N	450~460	DMA	20
3	TMEDA	450~460	DMA	80
4	DABCO	450~460	DMA	87
5	DBU	450~460	DMA	0
6	DABCO	456	DMA	81
7	DABCO	440	DMA	84
8	DABCO	390	DMA	92 (80)^c
9	DABCO	370	DMA	90
10	DABCO	390	DMF	90
11	DABCO	390	DMSO	85
12	DABCO	390	MeCN	46
13	DABCO	390	DCM	88
14	DABCO	390	MeOH	10
15	—	390	DMA	0
16	DABCO	—	DMA	0

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可见光诱导叔胺促进的烯烃酰基氟烷基化反应

Visible-Light-Driven Tertiary Amine-Promoted Acylfluoroalkylation of Alkenes

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