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2021 , Vol. 41 >Issue 12: 4766 - 4772

DOI: https://doi.org/10.6023/cjoc202109044

研究论文

N-无保护苯胺电化学硒醚化反应构建4-(烃基硒代)苯胺

  • 李文艺 ,
  • 唐胤恒 ,
  • 欧阳文韬 ,
  • 陆雨函 ,
  • 陈锦杨 ,
  • 何卫民
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  • a 衡阳师范学院化学与材料科学学院 湖南衡阳 421000
    b 南华大学化学化工学院 湖南衡阳 421001

收稿日期: 2021-09-28

  修回日期: 2021-10-30

  网络出版日期: 2021-11-03

基金资助

国家自然科学基金(21902014); 国家自然科学基金(22002037); 湖南省教育厅科学研究(19A068)

收起

Electrochemical Selenylation of N-Unprotected Anilines for Consturcing 4-(Organylselanyl)anilines

  • Wenyi Li ,
  • Yinheng Tang ,
  • Wentao Ouyang ,
  • Yuhan Lu ,
  • Jinyang Chen ,
  • Weimin He
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  • a College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421000
    b School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
* Corresponding authors. E-mail: ;

Received date: 2021-09-28

  Revised date: 2021-10-30

  Online published: 2021-11-03

Supported by

National Natural Science Foundation of China(21902014); National Natural Science Foundation of China(22002037); Scientific Research Hunan Provincial Education Department(19A068)

Fold

摘要

报道了一种无过渡金属催化剂、无化学氧化剂条件下N-无保护苯胺的电化学硒醚化反应. 该反应在非分隔电解槽中进行, 实现了温和电化学条件下4-(芳基硒代)苯胺和4-(烷基硒代)苯胺化合物的高效合成. 该反应具有良好的官能团兼容性和易放大等优点, 为合成4-(烃基硒代)苯胺类化合物提供了绿色实用的合成方法.

关键词： N-无保护苯胺; 二烃基二硒醚; 电化学合成; 温和条件; 绿色化学

本文引用格式

李文艺 , 唐胤恒 , 欧阳文韬 , 陆雨函 , 陈锦杨 , 何卫民 . N-无保护苯胺电化学硒醚化反应构建4-(烃基硒代)苯胺[J]. 有机化学, 2021 , 41(12) : 4766 -4772 . DOI: 10.6023/cjoc202109044

Abstract

A transition-metal-free and chemical oxidant-free method was developed for the uniform synthesis of 4-arylselanylanilines and 4-alkylselanylanilines through electrolytic selenylation of N-unprotected anilines with diorganyl diselenides under mild conditions in an undivided cell. The present approach had good functional group compatibility, which made it to be a green and practical method to synthesize 4-(organylselanyl)anilines.

Key words： N-unprotected anilines; diorganyl diselenides; electrochemical synthesis; mild conditions; green chemistry

参考文献

[1]
Amini, B.; Lowenkron, S. In Aniline and Its Derivatives, John Wiley & Sons, Inc., 2004, p. 783.
[2]
(a) Yue, H.; Bo, P.; Wang, b. L.; Lv, X.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2019, 39, 463. (in Chinese)
[2]
( 岳会兰, 鲍鹏丽, 王雷雷, 吕晓霞, 杨道山, 王桦, 魏伟, 有机化学, 2019, 39, 463.)
[2]
(b) Feng, E.; Hou, Z.; Xu, H. Chin. J. Org. Chem. 2019, 39, 1424. (in Chinese)
[2]
( 冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.)
[2]
(c) Liu, X.; Liu, Z.; Guo, Y.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Chin. J. Org. Chem. 2019, 39, 2001. (in Chinese)
[2]
( 刘雪滢, 刘振伟, 郭圆圆, 李敬亚, 邹大鹏, 吴豫生, 吴养洁, 有机化学, 2019, 39, 2001.)
[2]
(d) He, W.-B.; Gao, L.-Q.; Chen, X.-J.; Wu, Z.-L.; Huang, Y.; Cao, Z.; Xu, X.-H.; He, W.-M. Chin. Chem. Lett. 2020, 31, 1895.
[2]
(e) Ren, J.; Yan, X.; Cui, X.; Pi, C.; Wu, Y.; Cui, X. Green Chem. 2020, 22, 265.
[2]
(f) Gan, Z.; Li, G.; Yan, Q.; Deng, W.; Jiang, Y.-Y.; Yang, D. Green Chem. 2020, 22, 2956.
[2]
(g) Feng, Y.; Liu, Y.; Fu, Q.; Zou, Z.; Shen, J.; Cui, X. Chin. Chem. Lett. 2020, 31, 733.
[2]
(h) Wu, Y.; Pi, C.; Wu, Y.; Cui, X. Chem. Soc. Rev. 2021, 50, 3677.
[2]
(i) Wang, D.; Wang, S.-C.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chin. J. Chem. 2021, 39, 106.
[3]
(a) Chuai, H.; Zhang, S.-Q.; Bai, H.; Li, J.; Wang, Y.; Sun, J.; Wen, E.; Zhang, J.; Xin, M. Eur. J. Med. Chem. 2021, 223, 113621.
[3]
(b) Huang, Q.; Zhu, L.; Yi, D.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2020, 31, 373.
[3]
(c) Zhang, Z.; Qian, P.; Zha, Z. Chin. J. Org. Chem. 2019, 39, 1316. (in Chinese)
[3]
( 张振雷, 钱朋, 查正根, 有机化学, 2019, 39, 1316.)
[3]
(d) Zhang, T.-S.; Zhang, H.; Fu, R.; Wang, J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2019, 55, 13231.
[4]
Rodrigues, J.; Saba, S.; Joussef, A. C.; Rafique, J.; Braga, A. L. Asian J. Org. Chem. 2018, 7, 1819.
[5]
(a) Thurow, S.; Penteado, F.; Perin, G.; Jacob, R. G.; Alves, D.; Lenardão, E. J. Green Chem. 2014, 16, 3854.
[5]
(b) Ren, Y.; Xu, B.; Zhong, Z.; Pittman Jr, C. U.; Zhou, A. Asian J. Org. Chem. 2018, 7, 2439.
[5]
(c) Ren, Y.; Xu, B.; Zhong, Z.; Pittman, C. U.; Zhou, A. Org. Chem. Front. 2019, 6, 2023.
[5]
(d) Abenante, L.; Padilha, N. B.; Anghinoni, J. M.; Penteado, F.; Rosati, O.; Santi, C.; Silva, M. S.; Lenardão, E. J. Org. Biomol. Chem. 2020, 18, 5210.
[5]
(e) Meirinho, A. G.; Pereira, V. F.; Martins, G. M.; Saba, S.; Rafique, J.; Braga, A. L.; Mendes, S. R. Eur. J. Org. Chem. 2019, 2019, 6465.
[5]
(f) Saba, S.; Rafique, J.; Franco, M. S.; Schneider, A. R.; Espíndola, L.; Silva, D. O.; Braga, A. L. Org. Biomol. Chem. 2018, 16, 880.
[5]
(g) Rathore, V.; Kumar, S. Green Chem. 2019, 21, 2670.
[5]
(h) Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400.
[5]
(i) Zhao, R.; Yan, C.; Jiang, Y.; Cai, M. J. Chem. Res. 2018, 42, 584.
[5]
(j) Yu, C.; Shi, H.; Zhu, M.; Yan, J. Synlett 2015, 26, 2139.
[5]
(k) Lemir, I. D.; Castro-Godoy, W. D.; Heredia, A. A.; Schmidt, L. C.; Argüello, J. E. RSC Adv. 2019, 9, 22685.
[5]
(l) Ricordi, V. G.; Thurow, S.; Penteado, F.; Schumacher, R. F.; Perin, G.; Lenardão, E. J.; Alves, D. Adv. Synth. Catal. 2015, 357, 933.
[5]
(m) Zhou, Z.; He, X. Synth. Commun. 2018, 48, 2553.
[5]
(n) Kumaraswamy, G.; Ramesh, V.; Gangadhar, M.; Vijaykumar, S. Asian J. Org. Chem. 2018, 7, 1689.
[6]
(a) Yang, D.; Li, G.; Xing, C.; Cui, W.; Li, K.; Wei, W. Org. Chem. Front. 2018, 5, 2974.
[6]
(b) Wang, X.; Mu, S.; Sun, T.; Sun, K. Chin. J. Org. Chem. 2019, 39, 2802. (in Chinese)
[6]
( 王薪, 穆石强, 孙婷, 孙凯, 有机化学, 2019, 39, 2802.)
[6]
(c) Pan, C.; Liu, P.; Wu, A. g.; Li, M.; Wen, L.; Guo, W. Chin. J. Org. Chem. 2020, 40, 2855. (in Chinese)
[6]
( 潘超, 刘鹏, 武安国, 李明, 文丽荣, 郭维斯, 有机化学, 2020, 40, 2855.)
[6]
(d) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Yan, S.-S.; Deng, J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. J. Catal. 2021, 42, 1445.
[6]
(e) Chen, J.-Y.; Zhong, C.-T.; Gui, Q.-W.; Zhou, Y.-M.; Fang, Y.-Y.; Liu, K.-J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 475.
[6]
(f) Han, Y.; Cui, X. Chin. J. Org. Chem. 2021, 41, 2929. (in Chinese)
[6]
( 韩宇轩, 崔秀灵, 有机化学, 2021, 41, 2929.)
[7]
(a) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339.
[7]
(b) Zhang, H.; Tang, R.; Shi, X.; Xie, L.; Wu, J. Chin. J. Org. Chem. 2019, 39, 1837. (in Chinese)
[7]
( 张怀远, 唐蓉萍, 石星丽, 颉林, 伍家卫, 有机化学, 2019, 39, 1837.)
[7]
(c) Sun, K.; Lei, J.; Liu, Y.; Liu, B.; Chen, N. Adv. Synth. Catal. 2020, 362, 3709.
[7]
(d) Tang, H.-T.; Jia, J.-S.; Pan, Y.-M. Org. Biomol. Chem. 2020, 18, 5315.
[7]
(e) Liu, Y.; Han, Y.; Lin, L.; Xu, Y. Chin. J. Org. Chem. 2021, 41, 934. (in Chinese)
[7]
( 刘颖杰, 韩莹徽, 林立青, 许颖, 有机化学, 2021, 41, 934.)
[7]
(f) Zeyin, M.; Chengtao, F.; Kun, X. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese)
[7]
( 蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.)
[7]
(g) Wei, M.; Kun, X.; Bingbing, G.; Chengchu, Z. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese)
[7]
( 孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.)
[7]
(h) Zhou, Y.; Zhao, Z.; Zeng, L.; Li, M.; He, Y.; Gu, L. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese)
[7]
( 周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2021, 41, 1072.)
[7]
(i) Chen, N.; Xu, H.-C. Green Synth. Catal. 2021, 2, 165.
[8]
(a) Xiong, Y.; Zhang, J.; Shen, Q.; Huang, J.; Wang, T. Chin. J. Org. Chem. 2021, 41, 2735. (in Chinese)
[8]
( 熊云奎, 张健叶, 申裙, 黄嘉宇, 王涛, 有机化学, 2021, 41, 2735.)
[8]
(b) Zhao, Z.; Li, M.; Zhou, Y.; He, Y.; Zhang, L.; Li, G.; Gu, L. Chin. J. Org. Chem. 2021, 41, 2476. (in Chinese)
[8]
( 赵志恒, 李鸣, 周娅琴, 何永辉, 张丽珠, 李干鹏, 谷利军, 有机化学, 2021, 41, 2476.)
[8]
(c) Tang, H.; Pan, Y. Chin. J. Org. Chem. 2021, 41, 435. (in Chinese)
[8]
( 唐海涛, 潘英明, 有机化学, 2021, 41, 435.)
[8]
(d) Lian, F.; Xu, K. Chin. J. Org. Chem. 2020, 40, 3490. (in Chinese)
[8]
( 廉菲, 徐坤, 有机化学, 2020, 40, 3490.)
[8]
(e) Wu, Y.; Chen, J.-Y.; Liao, H.-R.; Shu, X.-R.; Duan, L.-L.; Yang, X.-F.; He, W.-M. Green Synth. Catal. 2021, 2, 233.
[8]
(f) Shen, H.; Cheng, D.; Li, Y.; Liu, T.; Yi, X.; Liu, L.; Ling, F.; Zhong, W. Green Synth. Catal. 2020, 1, 175.
[8]
(g) Wu, Z.-L.; Chen, J.-Y.; Tian, X.-Z.; Ouyang, W.-T.; Zhang, Z.-T.; He, W.-M. Chin. Chem. Lett. 2021, 10.1016/j.cclet.2021.08.071.
[8]
(h) Zhang, J.; Shi, S.-Q.; Hao, W.-J.; Dong, G.-Y.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2021, 86, 15886.
[9]
(a) Wang, Z.; Yang, L.; Liu, H.-L.; Bao, W.-H.; Tan, Y.-Z.; Wang, M.; Tang, Z.; He, W.-M. Chin. J. Org. Chem. 2018, 38, 2639. (in Chinese)
[9]
( 王峥, 杨柳, 刘慧兰, 谭英芝, 包文虎, 汪明, 唐子龙, 何卫民, 有机化学, 2018, 38, 2639.)
[9]
(b) Wu, Y.; He, W. Chin. J. Org. Chem. 2020, 40, 2597. (in Chinese)
[9]
( 吴燕, 何卫民, 有机化学, 2020, 40, 2597.)
[9]
(c) Yi, R.; He, W. Chin. J. Org. Chem. 2021, 41, 1267. (in Chinese)
[9]
( 易荣楠, 何卫民, 有机化学, 2021, 41, 1267.)
[9]
(d) Chen, X.; Xiao, F.; He, W.-M. Org. Chem. Front. 2021, 8, 5206.
[9]
(e) Sun, K.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921.
[9]
(f) Sun, L.-J.; Yuan, H.; Xu, J.-K.; Luo, J.; Lang, J.-J.; Wen, G.-B.; Tan, X.; Lin, Y.-W. Biochemistry 2021, 10.1021/acs.biochem.1c00554.
[9]
(g) Jiang, J.; Xiao, F.; He, W.-M.; Wang, L. Chin. Chem. Lett. 2021, 32, 1637.
[10]
Macagno, V. A.; Giordano, M. C.; Arvía, A. J. Electrochim. Acta 1969, 14, 335.
[11]
(a) Wan, J.-P.; Tu, Z.; Wang, Y. Chem.-Eur. J. 2019, 25, 6907.
[11]
(b) Banerjee, B.; Koketsu, M. Coord. Chem. Rev. 2017, 339, 104.
[12]
Zhang, S.; Koe, A.; Heintz, C.; Senior, A.; Jin, J. Tetrahedron Lett. 2016, 57, 260.
[13]
Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Tetrahedron Lett. 2003, 44, 7039.
[14]
Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V.; Khrustalev, V. N. Chem. Lett. 2010, 39, 720.
[15]
Ruberte, A. C.; Plano, D.; Encío, I.; Aydillo, C.; Sharma, A. K.; Sanmartín, C. Eur. J. Med. Chem. 2018, 157, 14.
[16]
Shaaban, S.; Ashmawy, A. M.; Negm, A.; Wessjohann, L. A. Eur. J. Med. Chem. 2019, 179, 515.
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