SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 8: 2476 - 2482

DOI: https://doi.org/10.6023/cjoc202002042

研究论文

铜催化苯并噻唑与二芳基碘鎓盐的芳基化反应

  • 李怀贵 ,
  • 杨澎 ,
  • 许峥 ,
  • 杜正银 ,
  • 傅颖
展开
  • 西北师范大学化学化工学院 兰州 730070

收稿日期: 2020-02-29

  修回日期: 2020-05-10

  网络出版日期: 2020-05-19

基金资助

国家自然科学基金（Nos.21262028，21762039，21762040）资助项目.

收起

Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts

  • Li Huaigui ,
  • Yang Peng ,
  • Xu Zheng ,
  • Du Zhengyin ,
  • Fu Ying
Expand
  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2020-02-29

  Revised date: 2020-05-10

  Online published: 2020-05-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21262028, 21762039, 21762040).

Fold

摘要

二芳基碘盐具有毒性低、反应条件温和及选择性高的优点，在有机合成中一直受到关注，已被广泛用作芳基化试剂，可用于芳杂环化合物的交叉偶联反应和芳基化反应等.发展了一种铜催化下苯并噻唑与二芳基碘鎓盐反应合成2-芳基苯并噻唑衍生物的方法.该方法具有底物范围广泛、基团耐受性良好及产率高等优点.

关键词： 苯并噻唑; 芳基化; 二芳基碘鎓盐; 交叉偶联反应; C-H键的活化

本文引用格式

李怀贵 , 杨澎 , 许峥 , 杜正银 , 傅颖 . 铜催化苯并噻唑与二芳基碘鎓盐的芳基化反应[J]. 有机化学, 2020 , 40(8) : 2476 -2482 . DOI: 10.6023/cjoc202002042

Abstract

Diaryliodonium salts have low toxicity and good stability, and their mediated reactions often have advantages of mild reaction conditions and high selectivity. They have received extensive attention and have been widely used as arylating agents in organic synthesis. A simple and efficient method for the synthesis of 2-arylbenzothiazole derivatives via copper-catalyzed C-H direct arylation of benzothiazoles with diaryliodonium salts as electrophilic arylating reagents was developed. This method shows wide range of substrates, good group tolerance, simple operation and high product yields.

Key words： benzothiazole; arylation; diaryliodonium salt; cross coupling; C-H activation

参考文献

[1] Matysiak, J.; Skrzypek, A.; Głaszcz, U.; Matwijczuk, A.; Senczyna, B.; Wietrzyk, J.; Krajewska-Kułak, E.; Niewiadomy, A. Res. Chem. Intermed. 2018, 44, 6169.
[2] Choi, S.; Park, H.; Lee, S.; Kim, S.; Hanc G.; Choo, H. Bioorg. Med. Chem. 2006, 14, 1229.
[3] Guo, H.; Li, J.; Shang, Y. Chin. Chem. Lett. 2009, 20, 1408.
[4] Benazzouz, A.; Boraud, T.; Dubédat, P.; Boireau, A.; Stutzmann, J.; Gross, C. Eur. J. Pharmacol. 1995, 284, 299.
[5] Bheeter, C. B.; Chen, L.; Soulé, J.-F.; Doucet, H. Catal. Sci. Technol. 2016, 6, 2005.
[6] (a) Hu, R.; Li, X.; Tong, Y.; Miao, D.; Pan, Q.; Jiang, Z.; Gan, H.; Han, S. Synlett 2016, 27, 1387.
(b) Yuen, O. Y.; So, C. M.; Wong, W. T.; Kwong, F. Y. Synlett 2013, 1549.
(c) Nagao, I.; Ishizaka T.; Kawanami, H. Green Chem. 2016, 18, 3494.
[7] (a) Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.; Wu, L.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273.
(b) Inamoto, K.; Nozawa, K.; Kondo, Y. Synlett 2012, 1678.
(c) Inamoto, K.; Hasegawa, C.; Kawasaki, J.; Hiroya, K.; Dohi, T. Adv. Synth. Catal. 2010, 352, 2643.
(d) Urzua, J. I.; Contreras, R.; Salas, C. O.; Tapia, R. A. RSC Adv. 2016, 6, 82401.
(e) Wang, P.; Tang, S. Green Chem. 2017, 19, 2092.
(f) Xu, Z.; Li, H.; Li, D. H.; Lang. J. Org. Lett. 2019, 21, 237.
[8] (a) Huang, C.; Wu, J.; Song, C.; Ding, R.; Qiao, Y.; Hou, H.; Chang, J.; Fan, Y. Chem. Commun. 2015, 51, 10353.
(b) Kirchberg, S.; Tani, S.; Ueda, K.; Yamaguchi, J.; Studer, A.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 2387.
(c) Zhang, F.; Greaney. M. Angew. Chem., Int. Ed. 2010, 49, 2768.
(d) Khake, S. M.; Soni, V.; Gonnade, B. R.; Punji, B. Dalton Trans. 2014, 43, 16084.
(e) Yang, J. Tetrahedron 2019, 75, 2182.
(f) Liu, C.; Yang, F. Chin. J. Chem. 2016, 34, 1213.
(g) Feng, J.; Li, B.; Jiang, J. Chin. J. Chem. 2018, 36, 11.
[9] (a) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
(b) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052.
[10] (a) Wirth, T. Angew. Chem., Int Ed. 2001, 40, 2812.
(b) Cai, Q.; Ma, H. Acta Chim. Sinica 2019, 77, 213(in Chinese). (蔡倩, 马浩文, 化学学报, 2019, 77, 213.)
(c) Wang, M.; Jiang, X. Acta Chim. Sinica 2018, 76, 377(in Chinese). (王明, 姜雪峰, 化学学报, 2018, 76, 377.)
[11] Kalyani, D.; Deprez, N. R.; Desai, N. R.; Sanford, L. V.; Kalyani, D.; Deprez, N. R.; Desai, L.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
[12] Wu, X.; Yang, Y.; Han, J.; Wang, L. Org. Lett. 2015, 17, 5654.
[13] Suero, M. G.; Bayle, E. D.; Collins, B. L.; Gaunt, M. J. Am. Chem. Soc. 2013, 135, 5332.
[14] Margraf, N.; Manolikakes, G. J. Org. Chem. 2015, 80, 2582.
[15] Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605.
[16] Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
[17] Qian, X.; Han, J.; Wang, L. Tetrahedron Lett. 2016, 57, 607.
[18] Zhu, D.; Liu, P.; Lu, W.; Wang, H.; Luo, B.; Hu, Y.; Huang, P.; Wen, S. Chem.-Eur. J. 2015, 21, 18915.
[19] Yang, P.; Wang, R.; Wu, H.; Du, Z.; Fu, Y. Asian J. Org. Chem. 2017, 6, 184.
[20] Gang, F.; Che, Y.; Du, Z.; Feng, H.; Fu, Y. Synlett 2017, 28, 1624.
[21] (a) Zhang, W.; Dong, T.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci. Ed.) 2019, 32, 35(in Chinese). (张文莹, 董涛生, 王天昀, 杜正银, 聊城大学学报(自然科学版), 2019, 32, 35.)
(b) Hu, B.; Zhang, Y.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci. Ed.) 2020, 33, 67(in Chinese). (胡贝, 张源民, 王天昀, 杜正银, 聊城大学学报(自然科学版), 2020, 33, 67.)
(c) Gang, F.; Xu, G.; Dong, T.; Yang, L.; Du, Z. Chin. J. Org. Chem. 2015, 35, 1428(in Chinese). (刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
[22] (a) Kumar, D.; Pilania, M.; Arun, V.; Pooniya, S. Org. Biomol. Chem. 2014, 12, 6340.
(b) Zhou, B.; Hou, W.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 1322.
[23] Deng, H.; Li, Z.; Ke, F.; Zhou, X. Chem.-Eur. J. 2012, 18, 4840.
[24] Yang, Z.; Chen, X.; Wang, S.; Liu, J.; Xie, K.; Wang, A.; Tan, Z. J. Org. Chem. 2012, 77, 7086.
[25] Duan, Z.; Ranjit, S.; Liu, X. Org. Lett. 2010, 12, 2430.
[26] Song, Q.; Feng, Q.; Zhou, M. Org. Lett. 2013, 15, 5990.
[27] Pratap, U. R.; Mali, J. R.; Jawale, D. W.; Mane, R. A. Tetrahedron Lett. 2009, 50, 1352.
[28] Prasad, D.; Sekar, G. Org. Lett. 2011, 13, 1008.
[29] Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008, 10, 5147.
[30] Alla, S. K.; Sadhu, P.; Punniyamurthy, T. J. Org. Chem. 2014, 79, 7502.
[31] Liu, S.; Chen, R.; Guo, X.; Yang, H.; Deng, G.; Li. C. Green Chem. 2012, 14, 1577.
[32] Auld, D. S.; Zhang, Y. Q.; Southal, N. T.; Rai, G.; Landsman, M.; MacLure, D.; Langevin, C. J.; Thomas, C. P.; Inglese, J. J. Med. Chem. 2009, 52, 1450.
[33] Weekes. A. A.; Bagley, M. C.; Westwell, A. D. Tetrahedron 2011, 67, 7743.
[34] Sayama, S. Heterocycles 2011, 83, 1267.
Options
文章导航

/

〈 〉