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2021 , Vol. 41 >Issue 6: 2302 - 2309

DOI: https://doi.org/10.6023/cjoc202102002

研究论文

空气氧化的铜催化苯甲酸衍生物邻位C(sp2)—H键的硒化反应

  • 孙名扬 ,
  • 徐坤 ,
  • 郭兵兵 ,
  • 曾程初
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  • 北京工业大学环境与生命学部 北京 100124

收稿日期: 2021-02-01

  修回日期: 2021-02-28

  网络出版日期: 2021-03-12

基金资助

国家自然科学基金(21871019)

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Copper-Catalyzed Vicinal C(sp2)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant

  • Mingyang Sun ,
  • Kun Xu ,
  • Bingbing Guo ,
  • Chengchu Zeng
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  • Faculty of Enviroment and Life Science, Beijing University of Technology, Beijing 100124
*Corresponding author.E-mail:

Received date: 2021-02-01

  Revised date: 2021-02-28

  Online published: 2021-03-12

Supported by

National Natural Science Foundation of China(21871019)

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摘要

报道了一种以二硒醚为硒基来源, 8-氨基喹啉为导向基的铜催化空气氧化的苯甲酸衍生物邻位C(sp2)—H键的硒化反应. 该方法仅需空气作为氧化剂, 避免了额外的化学氧化剂的使用, 同时具有较好的底物普适性和官能团兼容性.

关键词： 铜催化; C—H键活化; 硒化; 二硒醚; 8-氨基喹啉

本文引用格式

孙名扬 , 徐坤 , 郭兵兵 , 曾程初 . 空气氧化的铜催化苯甲酸衍生物邻位C(sp2)—H键的硒化反应[J]. 有机化学, 2021 , 41(6) : 2302 -2309 . DOI: 10.6023/cjoc202102002

Abstract

An efficient copper-catalyzed vicinal C(sp2)―H selenylation of benzoic acid dervatives is reported using diselenyl ether as selenyl resource, 8-aminoquinoline as the directing group. The protocol need only air as the terminal oxidant, avoiding the utilization of other external chemical oxidants, featuring good substrates generality and compatiblity of functional groups.

Key words： copper-catalyzed; C—H activation; selenylation reaction; diselenyl ether; 8-aminoquinoline

参考文献

[1]
(a) Govindasamy, M.; Wolf, W. M.; Helmut, S. Chem. Rev. 2001, 101,2125.
[1]
(b) Cristina, W. N.; Gilson, Z.; Joao, B. T. R. Chem. Rev. 2004, 104, 6255.
[1]
(c) Pang, Y. Q.; An, B. J.; Lou, L. L.; Zhang, J. S.; Yan, J.; Huang, L.; Li, X. S.; Yin, S. J. Med. Chem. 2017, 60,7300.
[2]
(a) Corinne, M.; Philippe, D. Org. Lett. 2000, 2,1705.
[2]
(b) Li, Y. M.; Wang, H. F.; Li, X. Y.; Chen, T.; Zhao, D. F. Tetrahedron 2010, 66,8583.
[3]
(a) Nobukazu, T. J. Org. Chem. 2007, 72,1241.
[3]
(b) Vanessa, G. R.; Camilo, S. F.; Gelson, P.; Eder, J. L.; Raquel, G. J.; Lucielli, S.; Diego, A. Green Chem. 2012, 14,1030.
[4]
(a) Michal, M.; Axel, J. W. Chem. Commun. 2013, 49,5507.
[4]
(b) Nirmalya, M.; Tanmay, C.; Brindaban, C. R. J. Org. Chem. 2013, 78,11110.
[5]
(a) Prasad, C. D.; Shah, J. B.; Amit, K.; Bhagat, S. B.; Kaustubh, S.; Soumava, B.; Sangit, K. J. Org. Chem. 2013, 78,1434.
[5]
(b) Vanessa, G. R.; Samuel, T.; Filipe, P.; Ricardo, F. S.; Gelson, P.; Eder, J. L.; Diego, A. Adv. Synth. Catal. 2015, 357,933.
[5]
(c) Zhang, X.; Wang, C. G.; Jiang, H.; Sun, L. H. Chem. Commun. 2018, 54,8781.
[5]
(d) Yeon, J. K.; Dae, Y. K. Tetrahedron Lett. 2019, 60,739.
[6]
(a) Sukalyan, B.; Amit, S.; Brindaban, C. R. J. Org. Chem. 2010, 75,4864.
[6]
(b) Thurow, S.; Penteado, F.; Perin, G.; Jacob, R. G.; Alves, D.; Lenardao, E. J. Green Chem. 2014, 16,3854.
[6]
(c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Tetrahedron Lett. 2003, 44,7039.
[7]
(a) Ren, P. X.; Qi, L.; Fang, Z. Y.; Wu, T. S.; Gao, Y. M.; Shen, S.; Song, J. Y.; Wang, L. J.; Li, W. Chin. J. Org. Chem. 2019, 39,1776(in Chinese).
[7]
(任培星, 齐林, 方卓越, 吴天舒, 高雅蒙, 沈松, 宋金燕, 王力竞, 李玮, 有机化学, 2019, 39,1776.)
[7]
(b) Wang, X.; Mu, S. Q.; Sun, T.; Sun, K. Chin. J. Org. Chem. 2019, 39,2802(in Chinese).
[7]
(王薪, 穆石强, 孙婷, 孙凯, 有机化学, 2019, 39,2802.)
[7]
(c) Sun, K.; Wang, S. N.; Feng, R. R.; Zhang, Y. X.; Wang, X.; Zhang, Z. G.; Zhang, B. Org. Lett. 2019, 21,2052.
[7]
(d) Wang, X.; Wang, Q. L.; Xue, Y. R.; Sun, K.; Wu, L. L.; Zhang, B. Chem. Commun. 2020, 56,4436.
[7]
(e) Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7,3100.
[8]
(a) Guy, R.; Naoto, C. Angew. Chem., Int. Ed. 2013, 52,11726.
[8]
(b) Supriya, R.; Yusuke, A.; Naoto, C. Chem. Rev. 2020, 120,1788.
[8]
(c) Wang, Y. L.; Zhang, L. B.; Niu, J. L.; Song, M. P. Chin. J. Org. Chem. 2019, 39,1761(in Chinese).
[8]
(王云龙, 张林宝, 牛俊龙, 宋毛平, 有机化学, 2019, 39,1761.)
[8]
(d) Zhang, M. F.; Li, R. P.; Yang, Z.; Feng, R. K. Chin. J. Org. Chem. 2020, 40,714(in Chinese).
[8]
(张梦帆, 李瑞鹏, 杨震, 冯若昆, 有机化学, 2020, 40,714.)
[9]
(a) Matthieu, C.; Floryan, D. C. Angew. Chem., Int. Ed. 2013, 52,9896.
[9]
(b) Liu, J. D.; Yu, L.; Zhuang, S. B.; Gui, Q. W.; Chen, X.; Wang, W. D.; Tan, Z. Chem. Commun. 2015, 51,6418.
[10]
Masayuki, I.; Yuta, T.; Kiyohiko, N.; Yasushi, N. Org. Lett. 2014, 16,4920.
[11]
Anup, M.; Harekrishna, S.; Mahiuddin, B. Org. Lett. 2016, 18,3202.
[12]
Bijaya, K. S.; Gurupada, B.; Ranjan, J. ChemistrySelect 2017, 2,9227.
[13]
(a) Xie, T. H.; Jiang, X. Y.; Mi, Z. S.; Li, X.; Xu, X. H.; Bai, R. R.; Shuai, Q.; Xie, Y. Y. Chin. J. Org. Chem. 2019, 39,3294(in Chinese).
[13]
(谢庭辉, 蒋筱莹, 米治胜, 李雪, 徐小河, 白仁仁, 帅棋, 谢媛媛, 有机化学, 2019, 39,3294.)
[13]
(b) Abdukader, A.; Wang, R.; Mamat, M.; Liu, C. J. Chin. J. Org. Chem. 2020, 40,1697(in Chinese).
[13]
( 阿布力米提•阿布都卡德尔, 汪荣, 买尔哈巴•买买提, 刘晨江, 有机化学, 2020, 40,1697.)
[13]
(c) Liu, K. J.; Wang, Z.; Lu, L. H.; Chen, J. Y.; Zeng, F.; Lin, Y. W.; Cao, Z.; Yu, X. Y.; He, W. M. Green Chem. 2021, 23,496.
[13]
(d) Cao, Z.; Zhu, Q.; Lin, Y. Wu.; He, W. M. Chin. Chem. Lett. 2019, 30,2132.
[14]
Liene, G.; Olafs, D. Angew. Chem., Int. Ed. 2014, 53,10209.
[15]
Ma, X. L.; Wang, Q.; Feng, X. Y.; Mo, Z. Y.; Pan, Y, M.; Chen, Y. Y.; Xin, M.; Xu, Y. L. Green Chem. 2019, 21,3547.
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