Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes

doi:10.6023/cjoc202310032

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 981-988.DOI: 10.6023/cjoc202310032 Previous Articles Next Articles

Special Issue: 有机氟化学合辑

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N-苄基丙烯酰胺的电化学三氟甲基化/螺环化合成三氟甲基取代2-氮杂螺[4.5]癸烷

周兰^a, 何红^a, 杨德巧^a, 侯中伟^a^,^*(), 王磊^a^,^b^,^c^,^*()

a 台州学院高等研究院药学院浙江台州 318000
b 杭州师范大学材料与化学化工学院有机硅化学及材料技术教育部重点实验室杭州 311121
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2023-10-31 修回日期:2023-12-16 发布日期:2024-04-02
基金资助:
国家自然科学基金(22071171); 国家自然科学基金(22101201); 浙江省自然科学基金(LZ22B020003); 浙江省自然科学基金(LQ22B020005)

Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes

Lan Zhou^a, Hong He^a, De-Qiao Yang^a, Zhong-Wei Hou^a(), Lei Wang^a^,^b^,^c()

a Advanced Research Institute, School of Pharmaceutical Sciences, Taizhou University, Taizhou, Zhejiang 318000
b College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2023-10-31 Revised:2023-12-16 Published:2024-04-02
Contact: *E-mail: zhongwei.hou@tzc.edu.cn; leiwang88@hotmail.com
Supported by:
National Natural Science Foundation of China(22071171); National Natural Science Foundation of China(22101201); Natural Science Foundation of Zhejiang Province(LZ22B020003); Natural Science Foundation of Zhejiang Province(LQ22B020005)

An electrochemical trifluoromethylation/spirocyclization of N-benzylacrylamides with CF₃SO₂Na as the source of trifluoromethyl group has been developed. This approach is carried out in a simple undivided cell at room temperature without relying on metal-reagents and oxidants, which provides a green and efficient route to construct a series of CF₃-containing 2-azaspiro[4.5]decanes. Furthermore, the gram-scale synthesis and transformation can be easily performed.

Key words: organic electrochemistry, trifluoromethylation, spirocyclization, spiroproduct

Cite this article

Lan Zhou, Hong He, De-Qiao Yang, Zhong-Wei Hou, Lei Wang. Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 981-988.

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N-苄基丙烯酰胺的电化学三氟甲基化/螺环化合成三氟甲基取代2-氮杂螺[4.5]癸烷

Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes

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References 19

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Entry	Variation from the standard conditions	Yield^b/%
1	None	78 (75)^c
2	2 (1 equiv.)	40
3	MeCN/H₂O (V∶V=13∶1)	70
4	MeCN	37
5	No KPF₆	47
6	15 mA, 1 h	55
7	6 mA, 4 h	44
8	No electricity	0
9	Me₄NBF₄	68
10	Et₄NBF₄	72
11	ⁿBu₄NBF₄	58
12	ⁿBu₄NPF₆	59
13	LiClO₄	70
14	0 ℃	67
15	60 ℃	69

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