Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group

doi:10.6023/cjoc201908036

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 724-730.DOI: 10.6023/cjoc201908036 Previous Articles Next Articles

铜促进8-氨基喹啉导向的芳基酰胺的二甲硫基化反应

郭圆圆^a, 刘振伟^a, 朱明祥^a, 李琳琳^a, 李敬亚^b, 邹大鹏^a, 吴豫生^b, 吴养洁^a

a 郑州大学化学与分子工程学院郑州 450052;
b 郑州泰基鸿诺医药股份有限公司郑州 450052

收稿日期:2019-08-27 修回日期:2019-11-05 发布日期:2020-04-02
通讯作者: 邹大鹏, 吴豫生, 吴养洁 E-mail:yusheng.wu@tetranovglobal.com;wyj@zzu.edu.cn;zdp@zzu.edu.cn
基金资助:
国家自然科学基金（Nos.21172200，21702191）资助项目.

Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group

Guo Yuanyuan^a, Liu Zhenwei^a, Zhu Mingxiang^a, Li Linlin^a, Li Jingya^b, Zou Dapeng^a, Wu Yusheng^b, Wu Yangjie^a

a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
b Tetranov Biopharm, LLC, Zhengzhou 450052

Received:2019-08-27 Revised:2019-11-05 Published:2020-04-02
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172200, 21702191).

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Abstract

Cu(II)-promoted dimethylthiolation of C(sp²)-H bonds using DMSO as the methylthiolation source with the assistance of an 8-aminoquinoline directing group have been developed. A number of dimethylthiolated benzamides were efficiently synthesized using CuSO₄·5H₂O as a promoter in moderate to good yields. In addition, this reaction system features facile conditions and no other oxidant additive was required.

Key words: Dimethylthiolation, DMSO, 8-Aminoquinoline, Copper-promoted

Cite this article

Guo Yuanyuan, Liu Zhenwei, Zhu Mingxiang, Li Linlin, Li Jingya, Zou Dapeng, Wu Yusheng, Wu Yangjie. Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 724-730.

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References

[1] (a) Vernon, M. W.; Heel, R. C.; Brogden, R. N. Drugs 1991, 42, 997.
(b) Martino, G. D.; Regina, G. L.; Coluccia, A.; Edler, M. C.; Barbera, M. C.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2004, 47, 6120.
(c) Martino, G. D.; Edler, M. C.; Regina, G. L.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947.
[2] (a) Superchi, S.; Rosini, C. Tetrahedron: Asymmetry 1997, 8, 349.
(b) Marom, H.; Antonov, S.; Popowski, Y.; Gozin, M. J. Org. Chem. 2011, 76, 5240.
(c) Kowalski, P.; Mitka, K.; Ossowska, K.; Kolarska, Z. Tetrahedron 2005, 61, 1933.
(d) Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Tetrahedron 2005, 61, 8315.
[3] (a) Truce, W. E.; Breiter, J. J. J. Am. Chem. Soc. 1962, 84, 1621.
(b) Lavanlsh, J. M. Tetrahedron Lett. 1973, 14, 3847.
(c) Hooper, J. F.; Young, R. D.; Weller, A. S.; Willis, M. C. Chem.- Eur. J. 2013, 19, 3125.
(d) Graham, T. H.; Liu, W.; Shen, D. M. Org. Lett. 2011, 13, 6232.
(e) Barbero, N.; Martin, R. Org. Lett. 2012, 14, 796.
[4] (a) Eberhart, A. J.; Imbriglio, J. E.; Procter, D. J. Org. Lett. 2011, 13, 5882.
(b) Ookubo, Y.; Wakamiya, A.; Yorimitsu, H.; Osuka, A. Chem.- Eur. J. 2012, 18, 12690.
(c) Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599.
(d) Modha, S. G.; Mehta, V. P.; Eycken, E. V. V. Chem. Soc. Rev. 2013, 42, 5042.
(e) Hooper, J. F.; Young, R. D.; Pernik, I.; Weller, A. S.; Willis, M. C. Chem. Sci. 2013, 4, 1568.
(f) Pan, F.; Wang, H.; Shen, P. X.; Zhao, J.; Shi, Z. J. Chem. Sci. 2013, 4, 1573.
(g) Quan, Z.-J.; Lv, Y.; Jing, F. Q.; Jia, X. D.; Huo, C. D.; Wang, X. C. Adv. Synth. Catal. 2014, 356, 325.
(h) Otsuka, S.; Fujino, D.; Murakami, K.; Yorimitsu, H.; Osuka, A. Chem.-Eur. J. 2014, 20, 13146.
[5] (a) Ram, V. J.; Agarwal, N. Tetrahedron Lett. 2001, 42, 7127.
(b) Sugahara, T.; Murakami, K.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed. 2014, 53, 9329.
(c) Wang, X.; Tang, Y.; Long, C.; Dong, W.; Li, C.; Xu, X.; Zhao, W.; Wang, X. Org. Lett. 2018, 20, 4749.
[6] Ralf, B.; Arnim, K.; Andreas, V. A.; Hartmut, A.; Simon, D.-R.; Lothar, W.; Isolde, H.-H.; Ines, H.; Elmar, G.; Christopher Hugh, R. WO 028579, 2012.
[7] For selected examples: (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
(b) Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. Org. Lett. 2009, 11, 5250.
(c) Chu, L. L.; Yue, X.; Qing, F. L. Org. Lett. 2010, 12, 1644.
(d) Luo, F.; Pan, C. D.; Li, L. P.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 5304.
(e) Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237.
(f) Jones-Mensah, E.; Magolan, J. Tetrahedron 2014, 55, 5323.
(g) Gao, X. F.; Pan, X. J.; Gao, J.; Jiang, H. F.; Yuan, G. Q.; Li, Y. W. Org. Lett. 2015, 17, 1038.
(h) Shen, T.; Huang, X. Q.; Liang, Y. F.; Jiao, N. Org. Lett. 2015, 17, 6186.
(i) Li, H. Y.; Xing, L. J.; Lou, M. M.; Wang, H.; Liu, R. H.; Wang, B. Org. Lett. 2015, 17, 1098.
(j) Sharma, P.; Rohilla, S.; Jain, N. J. Org. Chem. 2015, 80, 4116.
(k) Cui, X.; Liu, X.; Wang, X.; Tian, W.; Wei, D.; Huang, G. ChemistrySelect 2017, 2, 8607.
(l) Hu, L.; Chen, X.; Yu, L.; Yu, Y.; Tan, Z.; Zhu, G.; Gui, Q. Org. Chem. Front. 2018, 5, 216.
[8] (a) Pasto, D. J. J. Am. Chem. Soc. 1962, 84, 3777.
(b) Yamauchi, K.; Tanabe, T.; Kinoshita, M. J. Org. Chem. 1979, 44, 638.
(c) Fry, S. E.; Pienta, N. J. J. Org. Chem. 1984, 49, 4877.
(d) Tundo, P.; Rossi, L.; Loris, A. J. Org. Chem. 2005, 70, 2219.
(e) Basu, B.; Paul, S.; Nanda, A. K. Green Chem. 2010, 12, 767.
[9] (a) Ranken, P. F.; McKinnie, B. G. J. Org. Chem. 1989, 54, 2985.
(b) Stanetty, P.; Koller, H.; Mihovilovic, M. J. Org. Chem. 1992, 57, 6833.
(c) Pratt, S. A.; Goble, M. P.; Mulvaney, M. J.; Wuts, P. G. M. Tetrahedron Lett. 2000, 41, 3559.
(d) Fort, Y.; Rodriguez, A. L. J. Org. Chem. 2003, 68, 4918.
[10] (a) Martinek, M.; Korf, M.; Srogl, J. Chem. Commun. 2010, 46, 4387.
(b) Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Köhn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133, 19298.
(c) Sahoo, S. K.; Banerjee, A.; Chakraborty, S.; Patel, B. K. ACS Catal. 2012, 2, 544.
(d) Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 4972.
(e) Wu, Z.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu, Y. Org. Lett. 2013, 15, 1270.
(f) Niu, B.; Xu, L.; Xie, P.; Wang, M.; Zhao, W.; Pittman, C. U.; Zhou, A. ACS Comb. Sci. 2014, 16, 454.
(g) Corbet M.; Campo, F. D. Angew. Chem., Int. Ed. 2013, 52, 9896.
[11] For select reviews on transition-metal-catalyzed C—S bond formations, see: (a) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033.
(b) Kondo, T.; Mitsudo, T.-A. Chem. Rev. 2000, 100, 3205.
(c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(d) Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590.
(e) Postigo, A. RSC Adv. 2011, 1, 14. (f ) Liu, W.; Zhao, X. Synthesis 2013, 2051.
[12] Peng, J.-J.; Deng, Y. Q. Chin. J. Org. Chem. 2002, 22, 71(in Chinese). (彭家建, 邓友全, 有机化学, 2002, 22, 71.)
[13] (a) Zhang, J. H.; Hao, X. Q.; Wang, Z. L.; Ren, C. J.; Niu, J. L.; Song, M. P. Chin. J. Org. Chem. 2002, 22, 71(in Chinese). (张家恒, 郝新奇, 王正龙, 任常久, 牛俊龙, 宋毛平, 有机化学, 2017, 37, 1237.)
(b) Zhu, L. Z.; Cao, X.; Li, Y.; Liu, T.; Wang, X.; Qiu, R. H.; Yin, S. F. Chin. J. Org. Chem. 2017, 37, 1613(in Chinese). (朱龙志, 曹鑫, 李优, 刘婷, 王勰, 邱仁华, 尹双凤, 有机化学, 2017, 37, 1613.)
(c) Hao, W. Y.; Wang, Y. Y.; Yang, G. M.; Liu, Y. Y. Chin. J. Org. Chem. 2017, 37, 2678(in Chinese). (郝文燕, 王昱赟, 杨国敏, 刘云云, 有机化学, 2017, 37, 2678.)
(d) Hao, W. Y.; Wang, Y. Y.; Liu, Y. Y. Chin. J. Org. Chem. 2017, 37, 3198(in Chinese). (郝文燕, 王昱赟, 刘云云, 有机化学, 2017, 37, 3198.)
[14] (a) Han, S.; Liang, A.; Ren, X.; Gao, X.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2017, 58, 4859.

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铜促进8-氨基喹啉导向的芳基酰胺的二甲硫基化反应

Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group

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