Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow

doi:10.6023/cjoc202301023

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3239-3245.DOI: 10.6023/cjoc202301023 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

无支持电解质条件下连续流电化学合成三氟甲基化氧化吲哚

岁丹丹^a, 岑南楠^a, 龚若蕖^a, 陈阳^a, 陈文博^a^,^b^,^*()

a 上海电力大学环境与化学工程学院上海市电力材料防护与新材料重点实验室上海 200090
b 中国科学院上海有机化学研究所中国科学院能量调控材料重点实验室上海 200032

收稿日期:2023-01-29 修回日期:2023-05-07 发布日期:2023-05-23
基金资助:
上海市自然科学基金(20ZR1471600); 上海市科学技术委员会(19DZ2271100); 中国科学院能量调控材料重点实验室开放基金(ORFP2020-06)

Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow

Dandan Sui^a, Nannan Cen^a, Ruoqu Gong^a, Yang Chen^a, Wenbo Chen^a^,^b()

a Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, College of Environmental and Chemical Engineering, Shanghai University of Electric Power, Shanghai 200090
b CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2023-01-29 Revised:2023-05-07 Published:2023-05-23
Contact: * E-mail: wenbochen@shiep.edu.cn
Supported by:
Natural Science Foundation of Shanghai(20ZR1471600); Science and Technology Commission of Shanghai Municipality(19DZ2271100); Open Research Fund Program of CAS Key Laboratory of Energy Regulation Materials(ORFP2020-06)

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Abstract

A supporting electrolyte-free method for the electrochemical synthesis of trifluoromethylated oxindoles in conti- nuous flow was developed. Various N-arylacrylamides reacted with CF₃SO₂NHNHBoc smoothly to provide the corresponding products in moderate yields. The reaction scale-up was easily realized without changing the reaction conditions, which showed the application potential of continuous flow electrochemical synthesis.

Key words: trifluoromethyl, electrochemical synthesis, continuous flow, oxindole, green chemistry

Cite this article

Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.

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Entry	Deviation from standard conditions	Yield^b/%
1	—	53
2	CH₃CN as solvent	n.d.
3	CH₃CN/H₂O (V∶V=4∶1) as solvent	41
4	CH₃CN/H₂O (V∶V=8∶1) as solvent	45
5	24 mA	42
6	36 mA	44
7	48 mA	39
8	Reaction at r.t.	39
9	Reaction at 40 ℃	45
10	Reaction at 80 ℃	48
11	0.03 mL/min	20^c
12	0.09 mL/min	40
13	0.12 mL/min	31

Entry	Deviation from standard conditions	Yield^b/%
1	—	53
2	CH₃CN as solvent	n.d.
3	CH₃CN/H₂O (V∶V=4∶1) as solvent	41
4	CH₃CN/H₂O (V∶V=8∶1) as solvent	45
5	24 mA	42
6	36 mA	44
7	48 mA	39
8	Reaction at r.t.	39
9	Reaction at 40 ℃	45
10	Reaction at 80 ℃	48
11	0.03 mL/min	20^c
12	0.09 mL/min	40
13	0.12 mL/min	31

无支持电解质条件下连续流电化学合成三氟甲基化氧化吲哚

Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow

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