Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds

doi:10.6023/cjoc202406023

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (4): 1334-1341.DOI: 10.6023/cjoc202406023 Previous Articles Next Articles

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可见光介导下钯催化脂肪族α-溴代三氟甲基的脱溴还原反应

区洁晴^†, 屈培珍^†, 赵亮^*()

遵义医科大学药学院贵州遵义 563000

收稿日期:2024-06-17 修回日期:2024-09-22 发布日期:2024-10-18
作者简介:^† 共同第一作者
基金资助:
国家自然科学基金(21762053); 贵州省教育厅青年科技人才成长(2017-191)

Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds

Jieqing Ou^†, Peizhen Qu^†, Liang Zhao()

School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000

Received:2024-06-17 Revised:2024-09-22 Published:2024-10-18
Contact: * E-mail: zl1005@163.com
About author:^† The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21762053); Youth Science and Technology Talent Growth Project of Guizhou Provincial Department of Education(2017-191)

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Abstract

Due to its unique physicochemical properties, the trifluoromethyl group has been widely used in medicinal chemistry and materials science. Thus, the synthesis of organic compounds bearing trifluoromethyl groups has attracted considerable attention. However, the current methods for constructing aliphatic trifluoromethyl compounds are still very limited. In this paper, α-bromotrifluoromethyl compounds were used as raw materials and Pd(PPh₃)₄ was used as catalyst to achieve the hydrodebromination of alkyl α-trifluoromethyl bromides under visible light irradiation, generating a series of structurally diverse trifluoromethylated alkanes.

Key words: visible light mediated, palladium-catalyzed, α-bromotrifluoromethyl compounds, hydrodebromination

Cite this article

Jieqing Ou, Peizhen Qu, Liang Zhao. Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1334-1341.

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References 20

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Entry	Pd(PPh₃)₄(x mol%)	Base	Solvent	Yield^b/%
1	5.0	K₂CO₃	THF	97 (95)
2	2.5	K₂CO₃	THF	76
3	1.0	K₂CO₃	THF	7
4	2.5	Cs₂CO₃	THF	63
5	2.5	KOAc	THF	92 (84)
6	2.5	K₃PO₄	THF	64
7	2.5	KHCO₃	THF	41
8	2.5	KOAc	MeOH	15
9	2.5	KOAc	DCM	—
10	2.5	KOAc	DMSO	19
11	2.5	KOAc	1,4-Dioxane	47
12	2.5	—	THF	Trace
13^c	2.5	KOAc	THF	Trace
14	—	KOAc	THF	—
15^d	2.5	KOAc	THF	72

Entry	Pd(PPh₃)₄(x mol%)	Base	Solvent	Yield^b/%
1	5.0	K₂CO₃	THF	97 (95)
2	2.5	K₂CO₃	THF	76
3	1.0	K₂CO₃	THF	7
4	2.5	Cs₂CO₃	THF	63
5	2.5	KOAc	THF	92 (84)
6	2.5	K₃PO₄	THF	64
7	2.5	KHCO₃	THF	41
8	2.5	KOAc	MeOH	15
9	2.5	KOAc	DCM	—
10	2.5	KOAc	DMSO	19
11	2.5	KOAc	1,4-Dioxane	47
12	2.5	—	THF	Trace
13^c	2.5	KOAc	THF	Trace
14	—	KOAc	THF	—
15^d	2.5	KOAc	THF	72

可见光介导下钯催化脂肪族α-溴代三氟甲基的脱溴还原反应

Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds

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