SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 2: 641 - 649

DOI: https://doi.org/10.6023/cjoc202108023

研究论文

电化学氧化下喹喔啉-2(1H)-酮的三氟甲基化及电描述符对反应性能的评价

  • 锅小龙 ,
  • 王玉贤 ,
  • 赵志强 ,
  • 王庆 ,
  • 左剑 ,
  • 王陆瑶
展开
  • a 首都师范大学化学系 北京 100048
    b 首都师范大学物理系 北京 100048

收稿日期: 2021-08-16

  修回日期: 2021-09-19

  网络出版日期: 2022-02-24

基金资助

国家自然科学基金(22074095); “十三五”期间北京市属高校高水平教师(CIT&TCD20190330)

收起

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
Expand
  • 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)

Fold

摘要

通过使用廉价易得且易于处理的CF3SO2Na作为CF3源, 实现了操作简单的电化学氧化喹喔啉-2(1H)-酮的C—H三氟甲基化. 由于没有使用任何催化剂或氧化剂, 该方法符合绿色和可持续发展的要求. 最重要的是, 使用“电描述符图”来评估底物的反应活性, 可以清楚地看到反应/非反应边界和产量变化趋势.

关键词： 喹喔啉-2(1H)-酮; 电化学合成; 三氟甲基化; 三氟甲基亚磺酸钠; 电化学描述符

本文引用格式

锅小龙 , 王玉贤 , 赵志强 , 王庆 , 左剑 , 王陆瑶 . 电化学氧化下喹喔啉-2(1H)-酮的三氟甲基化及电描述符对反应性能的评价[J]. 有机化学, 2022 , 42(2) : 641 -649 . DOI: 10.6023/cjoc202108023

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.

Key words： qinoxalin-2(1H)-ones; electrochemical synthesis; trifluoromethylation; sodium trifluoromethanesulfinate; electro-descriptors

参考文献

[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.
Options
文章导航

/

〈 〉