ARTICLE

Electrochemical synthesis of 2-Indolinone through tetrabutylammonium carboxylate and N-arylacrylamides

  • 顾雄 ,
  • 王凯民 ,
  • 袁藤瑞 ,
  • 苟铨 ,
  • 樊保敏
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  • aSchool of Chemistry and Environment, Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China;
    bSchool of Chemistry and chemical engineering, Yangtze Normal University, Chongqing 408100, China

Received date: 2026-06-25

  Revised date: 2026-08-04

  Online published: 2026-09-22

Supported by

Yunnan Provincial Department of Education Science Research Fund Project (No. 2025Y0675), National Natural Science Foundation of China (No.22361025) and Natural Science Foundation of Chongqing (No. CSTB2023NSCQ-MSX0213).

Abstract

An efficient electrochemical synthesis of 2-Indolinone is reported in this paper. This method uses N-arylacrylamides as the starting material, employing commercially available tetrabutylammonium carboxylate as the alkylating agent and electrolyte, which generates the alkyl radical through anodic oxidative decarboxylation, and then affords a series of 2-Indolinone derivatives via radical cyclization. Compared with traditional approaches, this approach has the advantages of simple operation, mild reaction conditions and wide range of substrates, environmentally friendly, no extra oxidants or catalysts.

Cite this article

顾雄 , 王凯民 , 袁藤瑞 , 苟铨 , 樊保敏 . Electrochemical synthesis of 2-Indolinone through tetrabutylammonium carboxylate and N-arylacrylamides[J]. Chinese Journal of Organic Chemistry, 0 : 202604001 . DOI: 10.6023/cjoc202604001

References

[1] Guo B.-B.; M W.; Xu K.; Zeng, C.-C. Chin. J. Org. Chem.2021, 41, 2621-2635 (in Chinese).
(孟薇,徐坤,郭兵兵,曾程初,有机化学,2021,41,2621-2635.)
[2] Lu L.-Y.; Qiu, X.-D. Chin. J. Org. Chem.2024, 44, 1701-1718 (in Chinese).
(陆玲依,邱晓东,有机化学,2024,44,1701-1718)
[3] Mandal D.; Roychowdhury S.; Biswas J. P.; Maiti S.; Maiti, D. Chem. Soc. Rev.2022, 51, 7358-7426.
[4] Dong Z.; Ren Z.; Thompson S. J.; Xu Y.; Dong G.-B. Chem. Rev.2017, 117, 9333-9403.
[5] Lipinski C. A.; Lombardo F.; Dominy B. W.; Feeney, P. J. Adv. Drug Deliv. Rev.2001, 46, 3-26.
[6] Mooney R.; Masala M.; Martial T.; McGinness C.; Henriquez F. L.; Williams, R. A. M. Sci. Rep.2020, 10, 6420.
[7] Leeson P. D.; Springthorpe, B. Nat. Rev. Drug Discov.2007, 6, 881-890.
[8] Marti C.; Carreira, E. M. Eur. J. Org. Chem.2003, 2003, 2209-2219.
[9] Galliford C. V.; Scheidt, K. A. Angew. Chem. Int. Ed.2007, 46, 8748-8758.
[10] Singh G. S.; Desta, Z. Y. Chem. Rev.2012, 112, 6104-6155.
[11] Tan Y.-B.; Shu, H.-B; Huang H.-W.Chin. J. Org. Chem. 2025, 45, 2086-2108 (in Chinese).
(谭永波,舒洪波,黄华文,有机化学,2025,45,2086-2108.)
[12] Figueiredo G. S.; Zardo R. S.; Silva B. V.; Violante F. A.; Pinto A. C.; Fernandes, P. D. Pharmacol., Biochem. Behav.2013, 103, 431-439.
[13] Kamano Y.; Zhang H.-P.; Ichihara Y.; Kizu H.; Komiyama K.; Pettit, G. R. Tetrahedron Lett.1995, 36, 2783-2784.
[14] Bagal S. K.; Brown A. D.; Cox P. J.; Omoto K.; Owen R. M.; Pryde D. C.; Sidders B.; Skerratt S. E.; Stevens E. B.; Storer R. I.; Swain, N. A. J. Med. Chem.2013, 56, 593-624.
[15] Lv M.-J.; Li X.-X. ACS Catal.2021, 11, 14829-14835.
[16] Hou Y.; Huo J.-Y.; Li R.-X.; Hou J.; Lei P.; Wei H.-B.; Xie W.-Q. Org. Lett.2023, 25, 6949-6953.
[17] Wu Z.-L.; Luo W.; Ding R.; Xin C.; Wang C.-Y.; He, W.-M. Chin. J. Org. Chem.2025, 45, 3691-3700 (in Chinese).
(伍智林,罗伟,丁柔,辛翠,王从洋,何卫民,有机化学,2025,45,3691-3700.)
[18] Marchese A. D.; Larin E. M.; Mirabi B.; Lautens, M. Acc. Chem. Res.2020, 53, 1605-1619.
[19] Zhang Y.-Y.; Yan H.-B.; Zhu X.-J.; Shi Y.-J.; Li J.-X.; Yang D.-S.; Li, X.-F. Chin. J. Org. Chem.2026, 46, 653-663 (in Chinese).
(张云一,严含冰,朱先进,石永佳,李俊鑫,杨道山,李旭锋,有机化学,2026,46,653-663.)
[20] Matcha K.; Narayan R.; Antonchick A. P.Angew. Chem. Int. Ed. 2013, 52, 7985-7989.
[21] Zhang M.-Z.; Yang X.; Yin J.-X.; Deng Y.; Tan H.-Y.; Bai Y.-H.; Li Y.-L.; Wen J.-W.; Chen T.-Q. Org. Lett.2024, 26, 3923-3928.
[22] Hou H.; Ou W.; Su, C.-L. J. Org. Chem.2024, 89, 4120-4127.
[23] Sui D.-D.; Cen N.-N.; Gong R.-Q.; Chen Y.; Chen, W.-B. Chin. J. Org. Chem.2023, 43, 3239-3245 (in Chinese).
(岁丹丹,岑南楠,龚若蕖,陈阳,陈文博,有机化学,2023,43,3239-3245.)
[24] Xie Z.-G.; Li P.-H.; Hu Y.; Xu N.; Wang, L. Org. Biomol. Chem.2017, 15, 4205-4211.
[25] Qiu Z.-H.; Zheng W.-H.; Dai Y.-X.; Dong B.-C.; Cao T.; Jin H.-M.Chem. Commun. 2026, 62, 1959-1962.
[26] Biswas P.; Paul S.; Guin, J. Angew. Chem. Int. Ed.2016, 55, 7756-7760.
[27] Pan C.-D.; Fu Y.; Ni Q.-T.; Yu, J.-T. J. Org. Chem.2017, 82, 5005-5010.
[28] Zhang L.; Zhou H.-F.; Bai S.-K.; Li S.-D. Dalton Trans.2021, 50, 3201-3206.
[29] Xu X.-S.; Li X.-Q.; Chen H.-M.; Sun Z.T.; Yang H.; Mao F.-H.; Yan X.-H. Synlett.2022, 34, 63-66.
[30] Yang P.-Y.; Wang L.-L.; Yan M.; Yuan J.-W.; Xiao Y.-M.; Yang L.-R.; Xu X.-J.; Qu, L.-B. Org. Biomol. Chem.2025, 23, 1653-1661.
[31] Dai Q.; Yu J.-T.; Jiang Y.; Guo S.-J.; Yang H.-T.; Cheng J. Chem. Commun.2014, 50, 3865-3867
[32] Ding S.-Y.; Ren H.-P.; Zhu M.; Ma Q.; Miao Z.-C.; Li P.-F. Synth. Commun.2020, 51, 593-600.
[33] Jha A. K.; Nair D. P.; Arif M.; Yedase G. S.; Kuniyil R.; Yatham, V. R. J. Org. Chem.2023, 88, 15389-15394.
[34] Zhang S.-X.; Li Y.-F.; Wang T.; Li M.; Wen L.-R.; Guo W.-S. Org. Lett.2022, 24, 1742-1746.
[35] Wang X.-Y.; Zhong Y.-F.; Mo Z.-Y.; Wu S.-H.; Xu Y.-L.; Tang H.-T.; Pan, Y.-M. Adv. Synth. Catal.2020, 363, 208-214.
[36] Ruan Z.-X.; Huang Z.-X.; Xu Z.-N.; Mo, G.-Q; Tian X.; Yu X.-Y.; Ackermann L. Org. Lett.2019, 21, 1237-1240.
[37] Wang Y.; Wang Y.; Wang S.; Yu Z.; Wang S.-Q.; Chen, W.-B. J. Org. Chem.2024, 89, 11950-11958.
[38] Wang D.; Wan Z.-H.; Zhang H.; Alhumade H.; Yi H.; Lei A.-W. ChemSusChem.2021, 14, 5399-5404.
[39] Zhou, Z.-L; Yuan Y.; Cao, Y.-M; Qiao J.; Yao, A.-J; Zhao J.; Zuo, W.-Q; Chen, W.-J; Lei, A.-W. Chin. J. Chem.2019, 37, 611-615.
[40] Heard D. M.; Lennox, A. J. J. Angew. Chem. Int. Ed.2020, 59, 18866-18884.
[41] Fleischmann M.; Pletcher, D. R. Inst. Chem. Rev.1969, 2.
[42] Yan M.; Kawamata Y.; Baran, P. S. Chem. Rev.2017, 117, 13230-13319.
[43] Zhu C.-J.; Ang N. W. J.; Meyer T. H.; Qiu Y.-A.; Ackermann, L. ACS Cent. Sci.2021, 7, 415-431.
[44] Zhou H.-Y.; Tang H.-T.; He, W.-M. Chin. J. Catal.2023, 46, 4-10.
[45] Wu Y.-X.; Xi Y.-C.; Zhao M.; Wang, S.-Y. Chin. J. Org. Chem.2018, 38, 2590-2605 (in Chinese).
(吴亚星,席亚超,赵明,王思懿,有机化学,2018,38,2590-2605.)
[46] Hou Z.-S.; Zhou Q.-Q.; Ye M.; Ma W.-B.; Li D.-F.; Ding B.-J.; Chen M.-Y.; Gong X.-Q.;Yao, Y.-F. Chem. - Eur. J.2019, 25, 4206-4217.
[47] Lu M.-Q.; Xie E.-Q.; Song W.-J.; Wu T.; Cai H. Org. Lett.2026, 28, 3155-3160.
[48] Lu M.-Q.; Chen K.-L.; Wu T.; Cai, H. Angew. Chem. Int. Ed.2025, 64.
[49] Ayitou A. J.-L.; Sivaguru J. Chem. Commun.2011, 47, 2568-2570.
[50] Wu T.; Mu X.; Liu, G.-S. Angew. Chem. Int. Ed.2011, 50, 12578-12581.
[51] Zhao Y.-P.; Sharma N.; Sharma U. K.; Li Z.-H.; Song G.-H.; Van der Eycken, E. V. Chem. -Eur. J.2016, 22, 5878-5882.
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