ARTICLES

Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors

  • Xiaolong Guo ,
  • Yuxian Wang ,
  • Zhiqiang Zhao ,
  • Qing Wang ,
  • Jian Zuo ,
  • Luyao Wang
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  • a Department of Chemistry, Capital Normal University, Beijing, 100048
    b Department of Physics, Capital Normal University, Beijing, 100048
* Corresponding authors. E-mail: ;

Received date: 2021-08-16

  Revised date: 2021-09-19

  Online published: 2022-02-24

Supported by

National Natural Science Foundation of China(22074095); High-Level Teachers in Beijing Municipal Universities in the Period of 13th Five Year Plan(CIT&TCD20190330)

Abstract

An operationally simple electrochemical oxidative C—H trifluoromethylation of quinoxalin-2(1H)-ones was achieved by employing the inexpensive, readily available and easy processing CF3SO2Na as CF3 source. In the absence of any catalysts or oxidant reagents, this method is more in line with the requirements of green and sustainable development. Most importantly, “electric-descriptor-diagram” was used to evaluate the reaction substrates. The reactive/non-reactive boundary and the trend of yield change can been clearly seen.

Cite this article

Xiaolong Guo , Yuxian Wang , Zhiqiang Zhao , Qing Wang , Jian Zuo , Luyao Wang . Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors[J]. Chinese Journal of Organic Chemistry, 2022 , 42(2) : 641 -649 . DOI: 10.6023/cjoc202108023

References

[1]
(a) Weïwer, M.; Spoonamore, J.; Wei, J. Q.; Guichard, B.; Ross, N. T.; Masson, K.; Silkworth, W.; Dandapani, D.; Palmer, M.; Scherer, C. A.; Stern, A. M.; Schreiber, S. L.; Munoz, B. ACS Med. Chem. Lett. 2012, 3, 1034.
[1]
(b) Galal, S. A.; Khairat, S. H. M.; Ragab, F. A. F.; Abdelsamie, A. S.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; Diwani, I. E. D. Eur. J. Med. Chem. 2014, 86, 122.
[1]
(c) Hussain, S.; Parveen, S.; Hao, X.; Zhang, S.; Wang, W.; Qin, X.; Yang, Y.; Chen, X.; Zhu, S.; Zhu, C.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383.
[1]
(d) Pereira, J. A.; Pessoa, A. M.; Cordeiro, M. N. D.; Fernandes, R.; Prudêncio, C.; Noronha, J. P.; Vieira, M. Eur. J. Med. Chem. 2015, 97, 664.
[1]
(e) Qin, X.; Han, X. H. H.; Zhu, S.; Yang, Y.; Wu, B.; Hussain, S.; Parveen, S.; Jing, C.; Ma, B.; Zhu, C. J. Med. Chem. 2015, 58, 1254.
[1]
(f) Issa, D. A. E.; Habib, N. S.; Wahab, A. E. A. MedChemComm 2015, 6, 202.
[1]
(g) Cil, O.; Phuan, P.-W.; Lee, S.; Tan, J.; Haggie, P. M.; Levin, M. H.; Sun, L.; Thiagarajah, J. R.; Ma, T.; Verkman, A. S. Cell. Mol. Gastroenterol. Hepatol. 2016, 2, 317.
[2]
(a) Yang, L.; Gao, P.; Duan, X. H.; Gu, Y. R.; Guo, L. N. Org. Lett. 2018, 20, 1034.
[2]
(b) Yuan, J.; Fu, J.; Yin, J.; Dong, Z.; Xiao, Y.; Mao, P.; Qu, L. Org. Chem. Front. 2018, 5, 2820.
[2]
(c) Fu, J.; Yuan, J.; Zhang, Y.; Xiao, Y.; Mao, P.; Diao, X.; Qu, L. Org. Chem. Front. 2018, 5, 3382.
[2]
(d) Xue, W.; Su, Y.; Wang, K.-H.; Zhang, R.; Feng, Y.; Cao, L.; Huang, D.; Hu, Y. Org. Biomol. Chem. 2019, 17, 6654.
[2]
(e) Zheng, D.; Studer, A. Org. Lett. 2019, 21, 325.
[3]
(a) Yang, Q.; Han, X.; Zhao, J.; Zhang, H.-Y.; Zhang, Y. J. Org. Chem. 2019, 84, 11417.
[3]
(b) Jiang, X.; Yang, L.; Ye, Z.; Du, X.; Fang, L.; Zhu, Y.; Chen, K.; Li, J.; Yu, C. Eur. J. Org. Chem. 2020, 1687.
[4]
(a) Li, D.; Ma, H.; Yu, W. Adv. Synth. Catal. 2015, 357, 3696.
[4]
(b) Yin, K.; Zhang, R. Org. Lett. 2017, 19, 1530.
[4]
(c) Paul, S.; Ha, J. H.; Park, G. E.; Lee, Y. R. Adv. Synth. Catal. 2017, 359, 1515.
[4]
(d) Yuan, J. W.; Liu, S. N.; Qu, L. B. Adv. Synth. Catal. 2017, 359, 4197.
[4]
(e) Ramesh, B.; Reddy, C. R.; Kumar, G. R.; Reddy, B. V. S. Tetrahedron Lett. 2018, 59, 628.
[4]
(f) Toonchue, S.; Sumunnee, L.; Phomphrai, K.; Yotphan, S. Org. Chem. Front. 2018, 5, 1928.
[4]
(g) Paul, S.; Khanal, H. D.; Clinton, C. D.; Kim, S. H.; Lee, Y. R. Org. Chem. Front. 2019, 6, 231.
[5]
(a) Zeng, X.; Liu, X.; Wang, X.; Zhang, J.; Wang, X.; Hu, Y. Org. Biomol. Chem. 2017, 15, 8929.
[5]
(b) Yuan, J. W.; Fu, J. H.; Liu, X. N.; Xiao, Y. M.; Mao, P.; Qu, L. B. Org. Biomol. Chem. 2018, 16, 3203.
[6]
(a) Wei, Z.; Qi, S.; Xu, Y.; Liu, H.; Wu, Z.; Li, H.; Xia, C.; Duan, G. Adv. Synth. Catal. 2019, 361, 5490.
[6]
(b) Wang, J.; Sun, B.; Zhang, L.; Xu, T.; Xie, Y.; Jin, C. Asian J. Org. Chem. 2019, 8, 1942.
[7]
Zhan, Y.; Li, Y.; Tong, J.; Liu, P.; Sun, P. Eur. J. Org. Chem. 2021, 2193.
[8]
(a) Wang, L.; Liu, H.; Li, F.; Zhao, J.; Zhang, H.; Y.; Zhang, Y. Adv. Synth. Catal. 2019, 361, 2354.
[8]
(b) Hong, G.; Yuan, J.; Fu, J.; Wang, G.; Pan, Z.; Yang, L.; Xiao, Y.; Mao, P.; Zhang, X. Org. Chem. Front. 2019, 6, 1173.
[9]
(a) Gupta, A.; Deshmukh, M. S.; Jain, N. J. Org. Chem. 2017, 82, 4784.
[9]
(b) Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang, H. Org. Lett. 2018, 20, 7125.
[9]
(c) Yang, Q.; Yang, Z.; Tan, Y.; Zhao, J.; Sun, Q.; Zhang, H. Y.; Zhang, Y. Adv. Synth. Catal. 2019, 361, 1662.
[9]
(d) Li, K.; Xu, K.; Liu, Y.; Zeng, C.; Sun, B. Adv. Synth. Catal. 2019, 361, 1033.
[10]
Zhou, J.; Li, Z.; Sun, Z.; Ren, Q.; Zhang, Q.; Li, H.; Li, J. J. Org. Chem. 2020, 85, 4365.
[11]
(a) Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Chem. Commun. 2016, 52, 2846.
[11]
(b) Li, K.-J.; Jiang, Y.-Y.; Xu, K.; Zeng, C.-C.; Sun, B.-G. Green Chem. 2019, 21, 4412.
[12]
(a) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 11, 455.
[12]
(b) Purser, S.; Moore, P. R.; Swallowb, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[12]
(c) Nakajima, T. J. Fluorine Chem. 2013, 149, 104.
[12]
(d) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[12]
(e) Zhou, Y.; Wang, J.; Aceña, J. L. Chem. Rev. 2016, 116, 422.
[13]
(a) Kirsch, V. P. Modern Fluoroorganic Chemistry, Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, 2004.
[13]
(b) Furuya, T.; Kamlet, A.S.; Ritter, T. Nature 2011, 473, 470.
[13]
(c) Hu, L.; Chen, X.; Gui, Q.; Tan, Z.; Zhu, G. Chem. Commun. 2016, 52, 6845.
[13]
(d) Danoun, G.; Bayarmagnai, B.; Grünberg, M. F.; Gooßen, L. J. Angew. Chem., Int. Ed. 2013, 52, 7972.
[14]
(a) Sahoo, B.; Li, J.-L.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 11577.
[14]
(b) Sun, X.; Yu, S. Chem. Commun. 2016, 52, 10898.
[14]
(c) Verhoog, S.; Kee, C.W.; Wang, Y.; Khotavivattana, T.; Wilson, T. C.; Kersemans, V.; Smart, S.; Tredwell, M.; Davis, B. G.; Gouverneur, V. J. Am. Chem. Soc. 2018, 140, 1572.
[14]
(d) Chang, B.; Su, Y.; Huang, D.; Wang, K.; Zhang, W.; Shi, Y.; Zhang, X.; Hu, Y. J. Org. Chem. 2018, 83, 4365.
[14]
(e) Song, H.-X.; Han, Q.-Y.; Zhao, C.-L.; Zhang, C.-P. Green Chem. 2018, 20, 1662.
[14]
(f) Nishida, T.; Ida, H.; Kuninobu, Y.; Kanai, M. Nat. Commun. 2014, 5, 3387.
[14]
(g) Wang, F.; Tang, P. Chin. J. Org. Chem. 2020, 40, 1805. (in Chinese)
[14]
( 王峰, 汤平平, 有机化学, 2020, 40, 1805.)
[15]
(a) Wang, L.; Zhang, Y.; Li, F.; Hao, X.; Zhang, H. Y.; Zhao, J. Adv. Synth. Catal. 2018, 360, 3969.
[15]
(b) Xue, W.; Su, Y.; Wang, K. H.; Cao, L.; Feng, Y.; Zhang, W.; Huang, D.; Hu, Y. Asian J. Org. Chem. 2019, 8, 887.
[15]
(c) Dutta, N. B.; Gogoi, J. B. P.; Baishya, G. ChemsitrySelect 2021, 6, 1471.
[16]
(a) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492.
[16]
(b) Yan, M.; Kawamata, M.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
[16]
(c) Nutting, J. E.; Rafiee, M.; Stahl, S. S. Chem. Rev. 2018, 118, 4834.
[16]
(d) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485.
[16]
(e) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese)
[16]
( 孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.)
[16]
(f) Liu, Y.; Han, Y.; Lin, L.; Xu, Y. Chin. J. Org. Chem. 2021, 41, 934. (in Chinese)
[16]
( 刘颖杰, 韩莹徽, 林立青, 许颖, 有机化学, 2021, 41, 934.)
[16]
(g) Wang, X.; Xu, X.; Wang, Z.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2020, 40, 3738. (in Chinese)
[16]
( 王向阳, 徐学涛, 王振华, 方萍, 梅天胜, 有机化学, 2020, 40, 3738.)
[17]
(a) Amatore, C.; LeDuc, G.; Jutand, A. Chem. Eur. J. 2013, 19, 10082.
[17]
(b) Wang, F.; Stahl, S. S. Angew. Chem., Int. Ed. 2019, 58, 6385.
[17]
(c) Hickey, D. P.; Sandford, C.; Rhodes, Z.; Gensch, T.; Fries, L. R.; Sigman, M. S.; Minteer, S. D. J. Am. Chem. Soc. 2019, 114, 138.
[18]
O’Brien, A. G.; Maruyama, A.; Inokuma, Y.; Fujita, M.; Baran, P. S.; Blackmon, D. G. Angew. Chem., Int. Ed. 2014, 53, 11868.
[19]
Dou, G. Y.; Jiang, Y. Y.; Xua, K.; Zeng, C. C. Org. Chem. Front. 2019, 6, 2392.
[20]
Chen, Y.; Tian, B.; Cheng, Z.; Li, X.; Huang, M.; Sun, Y.; Liu, S.; Cheng, X.; Li, S.; Ding, M. Angew. Chem., Int. Ed. 2021, 60, 4199.
[21]
Guan, Z.; Wang, H.; Huang, Y.; Wang, Y.; Lei, A. Org. Lett. 2019, 21, 4619.
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