Chitosan@Cu-Catalyzed C3-Sulfenylation of Indoles with Sulfur Powder and Aryl Iodides

doi:10.6023/cjoc202001030

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2008-2017.DOI: 10.6023/cjoc202001030 Previous Articles Next Articles

壳聚糖@铜催化吲哚与硫粉和芳基碘化物的C3-硫醚化反应

成琳^a, 葛新^a, 刘学民^a, 冯云辉^b

a 江南大学化学与材料工程学院江苏无锡 214122;
b 广州大学体育教育系广州 510006

收稿日期:2020-01-23 修回日期:2020-04-29 发布日期:2020-05-08
通讯作者: 刘学民, 冯云辉 E-mail:lxm@jiangnan.edu.cn;13795553266@163.com
基金资助:
国家自然科学基金（No.21606104）资助项目.

Chitosan@Cu-Catalyzed C3-Sulfenylation of Indoles with Sulfur Powder and Aryl Iodides

Cheng Lin^a, Ge Xin^a, Liu Xuemin^a, Feng Yunhui^b

a School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122;
b Department of Physical Education, Guangzhou University, Guangzhou 510006

Received:2020-01-23 Revised:2020-04-29 Published:2020-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21606104).

1. 202008S.pdf(1772KB)

Abstract

Aiming at the problem that the catalyst can not be recovered during the construction of the C-S bond in the indole ring with sulfur powder as the sulfur source, 2-pyridinecarboxylic acid modified chitosan (PACS) catalyst with different type of copper was prepared, which was used to catalyze the three-component reaction of indole, sulfur powder and iodobenzene to prepare C-3 thioether-based indole in a one-pot method. The reaction yield is as high as 92%, and the substrate has good applicability. The most suitable catalyst[PACS@Cu(OAc)₂] was characterized and analyzed by thermogravimetric analysis (TGA), scanning electron microscope(SEM), X-ray photoelectron spectroscopy(XPS), etc. It shows that the catalyst has the advantages of no additional ligand, easy separation and reusable.

Key words: chitosan, indole, sulfur powder, catalyze, heterogeneous

Cite this article

Cheng Lin, Ge Xin, Liu Xuemin, Feng Yunhui. Chitosan@Cu-Catalyzed C3-Sulfenylation of Indoles with Sulfur Powder and Aryl Iodides[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2008-2017.

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[1] (a) Chung, W. J.; Griebel, J. J.; Kim, E. T.; Yoon, H.; Simmonds, A. G.; Ji, H. J.; Dirlam, P. T.; Glass, R. S.; Wie, J. J.; Nguyen, N. A.; Guralnick, B. W.; Park, J.; Somogyi, A.; Theato, P.; Mackay, M. E.; Sung, Y.-E.; Char, K.; Pyun, J. Nat. Chem. 2013, 5, 518.
(b) Horita, Y.; Takii, T.; Chiba, T.; Kuroishi, R.; Maeda, Y.; Kurono, Y.; Onozaki, K. Bioorg. Med. Chem. Lett. 2009, 19, 6313.
(c) Ruan, L.; Fan, R.; Liu, X.; Chen, J.; Weng, J. Chin. J. Org. Chem. 2015, 35, 1166(in Chinese). (阮铃莉, 范人杰, 刘幸海, 陈杰, 翁建全, 有机化学, 2015, 35, 1166.)
(d) Lee, E.-J.; Kim, K.-W.; Kim, G.-H.; Park, C.-E.; Choi, J.-H. Fibers Polym. 2018, 19, 1791.
[2] (a) Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521.
(b) Chekler, E. L. P.; Elokdah, H. M.; Butera, J. Tetrahedron Lett. 2008, 49, 6709.
[3] (a) Pourshab, M.; Asghari, S.; Mohseni, M. J. Heterocycl. Chem. 2018, 55, 173.
(b) Zhang, B.; Kang, Y.; Shi, R. Chin. J. Org. Chem. 2016, 36, 1814(in Chinese). (张变香, 亢永强, 史瑞雪, 有机化学, 2016, 36, 1814.)
[4] Funk, C. D. Nat. Rev. Drug Discovery 2005, 4, 664.
[5] La Regina, G.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; De Martino, G.; Matesanz, R.; Diaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865.
[6] La Regina, G.; Coluccia, A.; Brancale, A.; Piscitelli, F.; Famiglini, V.; Cosconati, S.; Maga, G.; Samuele, A.; Gonzalez, E.; Clotet, B.; Schols, D.; Este, J. A.; Novellino, E.; Silvestri, R. J. Med. Chem. 2012, 55, 6634.
[7] Lavekar, A. G.; Equbal, D.; Saima; Sinha, A. K. Adv. Synth. Catal. 2018, 360, 180.
[8] Gandeepan, P.; Koeller, J.; Ackermann, L. ACS Catal. 2017, 7, 1030.
[9] Liu, X. X.; Cui, H. H.; Yang, D. S.; Dai, S. C.; Zhang, G. Q.; Wei, W.; Wang, H. Catal. Lett. 2016, 146, 1743.
[10] Luckhurst, C. A.; Millichip, I.; Parker, B.; Reuberson, J.; Furber, M. Tetrahedron Lett. 2007, 48, 8878.
[11] (a) Wang, C. C.; Wang, Z. H.; Wang, L.; Chen, Q.; He, M. Y. Chin. J. Chem. 2016, 34, 1081.
(b) Fan, W. G.; Yang, Q.; Xu, F. S.; Li, P. X. J. Org. Chem. 2014, 79, 10588.
[12] (a) Jones, J. M.; Dupont, V. A.; Brydson, R.; Fullerton, D. J.; Nasri, N. S.; Ross, A. B.; Westwood, A. V. K. Catal. Today 2003, 81, 589.
(b) Chu, H.; Wu, L. W. J. Environ. Sci. Health, Part A 1998, 33, 1119.
[13] Rostami, A.; Rostami, A.; Iranpoor, N.; Zolfigol, M. A. Tetrahedron Lett. 2016, 57, 192.
[14] (a) Wu, W.; Ding, Y. C.; Xie, P.; Tang, Q. J.; Pittman, C. U.; Zhou, A. H. Tetrahedron 2017, 73, 2151.
(b) Guo, T.; Wei, X. N.; Wang, H. Y.; Zhu, Y. L.; Zhao, Y. H.; Ma, Y. C. Org. Biomol. Chem. 2017, 15, 9455.
(c) Guo, T.; Wei, X. N.; Zhu, Y. L.; Chen, H.; Han, S. L.; Ma, Y. C. Synlett 2018, 29, 1530.
(d) Ravi, C.; Reddy, N. N. K.; Pappula, V.; Samanta, S.; Adimurthy, S. J. Org. Chem. 2016, 81, 9964.
(e) Thanh Binh, N.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2013, 15, 4218.
[15] Xiong, J.; Zhong, G. F.; Liu, Y. Y. Adv. Synth. Catal. 2019, 361, 550.
[16] Shibahara, F.; Kanai, T.; Yamaguchi, E.; Kamei, A.; Yamauchi, T.; Murai, T. Chem. Asian J. 2014, 9, 237.
[17] Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2016, 81, 7771.
[18] Ge, X.; Cheng, L.; Sun, F. L.; Liu, X. M.; Chen, X. Z.; Qian, C.; Zhou, S. D. Catal. Commun. 2019, 123, 32.
[19] Thanh Binh, N. Adv. Synth. Catal. 2017, 359, 1066.
[20] (a) Wang, S.; Zhou, H.; Song, S.; Wang, J. Chin. J. Org. Chem. 2015, 35, 85(in Chinese). (王硕, 周宏勇, 宋沙沙, 王家喜, 有机化学, 2015, 35, 85.)
(b) Yu, D.; Wu, M.; Hu, Q.; Wang, L.; Lv, C.; Zhang, L. J. Hazard. Mater. 2019, 367, 456.
(c) Masuda, K.; Ichitsuka, T.; Koumura, N.; Sato, K.; Kobayashi, S. Tetrahedron 2018, 74, 1705.
[21] Bahuguna, A.; Kumar, A.; Kumar, S.; Chhabra, T.; Krishnan, V. ChemCatChem 2018, 10, 3121.
[22] Hong, K. B.; Lee, C. W.; Yum, E. K. Tetrahedron Lett. 2004, 45, 693.
[23] Siddiki, S.; Kon, K.; Shimizu, K. Chem-Eur. J. 2013, 19, 14416.
[24] (a) Tukhani, M.; Panahi, F.; Khalafi-Nezhad, A. ACS Sustainable Chem. Eng. 2018, 6, 1456.
(b) Dong, Y.; Bi, J.; Zhu, D.; Meng, D.; Ming, S.; Guo, W.; Chen, Z.; Liu, Q.; Guo, L.; Li, T. Cellulose 2019, 26, 7355.
(c) Liu, B.; Zhou, H.; Li, Y.; Wang, J. Chin. J. Org. Chem. 2014, 34, 2554(in Chinese). (刘兵, 周宏勇, 李云庆, 王家喜, 有机化学, 2014, 34, 2554.)
[25] Liu, X. M.; Chang, S.; Chen, X. Z.; Ge, X.; Qian, C. New J. Chem. 2018, 42, 16013.
[26] Baran, T.; Mentes, A.; Arslan, H. Int. J. Biol. Macromol. 2015, 72, 94.
[27] Chen, H.-Y.; Peng, W.-T.; Lee, Y.-H.; Chang, Y.-L.; Chen, Y.-J.; Lai, Y.-C.; Jheng, N.-Y.; Chen, H.-Y. Organometallics 2013, 32, 5514.
[28] Gu, F.; Geng, J.; Li, M.; Chang, J.; Cui, Y. ACS Omega 2019, 4, 21421.
[29] Wang, Y.; Liu, Q.; Xu, M.; Shu, G.; Jiang, M.; Fei, G.; Zeng, M. J. Macromol. Sci. B 2017, 56, 670.
[30] Jiang, Y.; Wang, Y.; Han, Q.; Zhu, R.; Xiong, X. Chin. J. Org. Chem. 2014, 34, 2068(in Chinese). (江云兵, 王彦龙, 韩骞, 朱荣俊, 熊兴泉, 有机化学, 2014, 34, 2068.)
[31] Frindy, S.; Kadib, A.; Lahcini, M.; Primo, A.; Garcia, H. ChemCatChem 2015, 7, 3307.
[32] Wang, L.; Li, B.; Xu, F.; Shi, X.; Feng, D.; Wei, D.; Li, Y.; Feng, Y.; Wang, Y.; Jia, D.; Zhou, Y. Biosens. Bioelectron. 2016, 79, 1.
[33] Verma, S. K.; Ghorpade, R.; Pratap, A.; Kaushik, M. P. Green Chem. 2012, 14, 326.
[34] Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2012, 48, 11686.
[35] Wang, P.; Tang, S.; Huang, P.; Lei, A. Angwe. Chem., Int. Ed. 2017, 56, 3009.
[36] Chen, M.; Luo, Y.; Zhang, C.; Guo, L.; Wang, Q.; Wu, Y. Org. Chem. Front. 2019, 6, 116.
[37] Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J.; Praneeth, K. Synthesis 2009, 9, 1520.

壳聚糖@铜催化吲哚与硫粉和芳基碘化物的C3-硫醚化反应

Chitosan@Cu-Catalyzed C3-Sulfenylation of Indoles with Sulfur Powder and Aryl Iodides

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