Citation: Ren Peixing, Qi Lin, Fang Zhuoyue, Wu Tianshu, Gao Yameng, Shen Song, Song Jinyan, Wang Lijing, Li Wei. Copper-Catalyzed Sulfeno-/Seleno-amination of β, γ-Unsaturated Hydrazones with Disulfides/Diselenides toward Sulfenylated/Selenylated Pyrazolines[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1776-1786. doi: 10.6023/cjoc201901006 shu

Copper-Catalyzed Sulfeno-/Seleno-amination of β, γ-Unsaturated Hydrazones with Disulfides/Diselenides toward Sulfenylated/Selenylated Pyrazolines

Ren Peixing ^a ,
Qi Lin ^a,, ,
Fang Zhuoyue ^a ,
Wu Tianshu ^a ,
Gao Yameng ^a ,
Shen Song ^a ,
Song Jinyan ^a ,
Wang Lijing ^a,b,, ,
Li Wei ^a,b,,

a.
College of Chemistry & Environmental Science, Hebei University, Baoding 071002
b.
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, Baoding 071002

Corresponding author: Qi Lin, 129qilin@163.com Wang Lijing, wanglj@hbu.edu.cn Li Wei, liweihebeilab.163.com
Received Date: 5 January 2019
Revised Date: 26 January 2019
Available Online: 22 June 2019
Fund Project: the Science Foundation for Key Program of Hebei Province B2016201031Project supported by the National Natural Science Foundation of China (No. 21702043), the Science Foundation for Key Program of Hebei Province (No. B2016201031), the Science Foundation for Youths of Hebei Province (No. B2017201041), and the "Revolution of Scientific Research Results into Teaching Resources" of Hebei University (No. KYZJX18140)the "Revolution of Scientific Research Results into Teaching Resources" of Hebei University KYZJX18140the National Natural Science Foundation of China 21702043the Science Foundation for Youths of Hebei Province B2017201041

Figures(2)

A convenient copper-catalyzed sulfeno-/seleno-amination of β, γ-unsaturated hydrazones with disulfides/diselenides via radical pathway has been developed. The protocol enables efficient access to various sulfenylated/selenylated pyrazolines under mild reaction conditions.
- copper-catalyzed,
- β, γ-unsaturated hydrazones,
- sulfeno-/selenoamination,
- pyrazoline
1. [1]
  (a) Cremlyn, R. J. An Introduction to Organosulfur Chemistry, John Wiley and Sons, Chichester, U.K., 1996.
  (b) Fontecave, M.; Ollagnierde-Choudens, S.; Mulliez, E. Chem. Rev. 2003, 103, 2149.
2. [2]
  (a) Yu, L.; Dennis, E. A. J. Am. Chem. Soc. 1992, 114, 8757.
  (b) Wang, X.; Shaaban, K. A.; Elshahawi, S. I.; Ponomareva, L. V.; Sunkara, M.; Zhang, Y.; Copley, G. C.; Hower, J. C.; Morris, A. J.; Kharel, M. K.; Thorson, J. S. J. Nat. Prod. 2013, 76, 1441.
  (c) Singh, S. B.; Zink, D. L.; Dorso, K.; Motyl, M.; Salazar, O.; Basilio, A.; Vicente, F.; Byrne, K. M.; Ha, S.; Genilloud, O. J. Nat. Prod. 2009, 72, 345.
3. [3]
  (a) Lauterbach, C.; Fabian, J. Eur. J. Inorg. Chem. 1999, 1999, 1995.
  (b) Hope, E. G.; Levason, W. Coord. Chem. Rev. 1993, 122, 109.
  (c) Clemenson, P. I. Coord. Chem. Rev. 1990, 106, 171.
  (d) Baumann, R. P.; Ishiguro, K.; Penketh, P. G.; Shyam, K.; Zhu, R.; Sartorelli, A. C. Biochem. Pharmacol. 2011, 81, 1201.
4. [4]
  (a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
  (b) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X. Chem. Soc. Rev. 2015, 44, 291.
  (c) Li, H.; Wang, Z.; Deng, W. Chin. J. Org. Chem. 2016, 36, 2419 (in Chinese).
  (李红亮, 王正林, 邓卫平, 有机化学, 2016, 36, 2419.)
  (d) 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.)
  (e) Wang, D.; Zhang, R.; Lin, S.; Deng, R.; Yan, Z. Chin. J. Org. Chem. 2016, 36, 2757 (in Chinese).
  (王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.)
  (f) Wang, J.; Wu, J.; Tian, W. Chin. J. Chem. 2015, 33, 632.
  (g) Hu, D.; Bai, F.; Liu, Y.; Wan, J.-P. Chin. J. Chem. 2016, 34, 1053.
  (h) Zhang, P.; Lu, L.; Shen, Q. Acta Chim. Sinica 2017, 75, 744 (in Chinese).
  (张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.)
  (i) Zheng, G.; Zhao, J.; Li, Z.; Zhang, Q.; Sun, J.; Sun, H.; Zhang, Q. Chem. Eur. J. 2016, 22, 3513.
5. [5]
  (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
  (b) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981.
  (c) Brandi, A.; Cardona, F.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem.-Eur. J. 2009, 15, 7808.
  (d) Beckwith, A. L. J.; Wagner, R. D. J. Org. Chem. 1981, 46, 3638.
  (e) Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarstrom, S. J. Am. Chem. Soc. 1980, 102, 1436.
  (f) Pironti, V.; Colonna, S. Green Chem. 2005, 7, 43.
  (g) Chen, M.; Wang, L.-J.; Li, W. Chin. J. Org. Chem. 2017, 37, 1173 (in Chinese).
  (陈漫漫, 王力竞, 李玮, 有机化学, 2017, 37, 1173.)
6. [6]
  (a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
  (b) Li, D.; Mao, T.; Huang, J.; Zhu, Q. Chem. Commun. 2017, 53, 3450.
7. [7]
  (a) Zheng, Y.; He, Y.; Rong, G.; Zhang, X.; Weng, Y.; Dong, K.; Xu, X.; Mao, J. Org. Lett. 2015, 17, 5444.
  (b) Cui, H.; Liu, X.; Wei, W.; Yang, D.; He, C.; Zhang, T.; Wang, H. J. Org. Chem. 2016, 81, 2252.
  (c) Wang, D.; Yan, Z.; Xie, Q.; Zhang, R.; Lin, S.; Wang, Y. Org. Biomol. Chem. 2017, 15, 1998.
8. [8]
  (a) Denmark, S. E.; Collins, W. R.; Cullen, M. D. J. Am. Chem. Soc. 2009, 131, 3490.
  (b) Denmark, S. E.; Hartmann, E.; Kornfilt, D. J. P.; Wang, H. Nat. Chem. 2014, 6, 1056.
  (c) Denmark, S. E.; Chi, H. M. J. Am. Chem. Soc. 2014, 136, 8915.
  (d) Alom, N.-E.; Rina, Y. A.; Li, W. Org. Lett. 2017, 19, 6204.
  (e) Alom, N.-E.; Wu, F.; Li, W. Org. Lett. 2017, 19, 930.
  (f) Ni, Y.; Zuo, H.; Li, Y.; Wu, Y.; Zhong, F. Org. Lett. 2018, 20, 4350−4353.
  (g) Liu, T.; Tian, J.; Gao, W.-C.; Chang, H.-H.; Liu, Q.; Li, X.; Wei, W.-L. Org. Biomol. Chem. 2017, 15, 5983.
9. [9]
  (a) Lee, M.; Brockway, O.; Dandavati, A.; Tzou, S.; Sjoholm, R.; Satam, V.; Westbrook, C.; Mooberry, S. L.; Zeller, M.; Babu, B.; Lee, M. Eur. J. Med. Chem. 2011, 46, 3099.
  (b) Lombardino, J. G.; Otterness, I. G. J. Med. Chem. 1981, 24, 830.
  (c) Alex, J. M.; Kumar, R. J. J. Enzyme Inhib. Med. Chem. 2014, 29, 427.
  (d) Dardic, D.; Lauro, G.; Bifulco, G.; Laboudie, P.; Sakhaii, P.; Bauer, A.; Vilcinskas, A.; Hammann, P. E.; Plaza, A. J. Org. Chem. 2017, 82, 6032.
10. [10]
  (a) Duan, X.-Y.; Zhou, N.-N.; Fang, R.; Yang, X.-L.; Yu, W.; Han, B. Angew. Chem., Int. Ed. 2014, 53, 3158.
  (b) Zhu, M.-K.; Chen, Y.-C.; Loh, T.-P. Chem.-Eur. J. 2013, 19, 5250.
  (c) Zhu, X.; Chiba, S. Org. Biomol. Chem. 2014, 12, 4567.
  (d) Zhao, Q.-Q.; Chen, J.; Yan, D.-M.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2017, 19, 3620.
  (e) Wei, Q.; Chen, J.-R.; Hu, X.-Q.; Yang, X.-C.; Lu, B.; Xiao, W.-J. Org. Lett. 2015, 17, 4464.
  (f) Yang, M.-N.; Yan, D.-M.; Zhao, Q.-Q.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2017, 19, 5208.
11. [11]
  (a) Chen, M.; Wang, L.-J.; Ren, P.-X.; Hou, X.-Y.; Fang, Z.; Han, M.-N.; Li, W. Org. Lett. 2018, 20, 510.
  (b) Chen, M.; Qi, L.; Chen, J.-M.; Ren, P.-X.; Du, J.; Wang, L.-J.; Li, W. Org. Biomol. Chem. 2018, 16, 5136.
  (c) Wang, L.-J.; Ren, P.-X.; Qi, L.; Chen, M.; Lu, Y.-L.; Zhao, J.-Y.; Liu, R.; Chen, J.-M.; Li, W. Org. Lett. 2018, 20, 4411.
12. [12]
  Yu, J.-M.; Cai, C. Org. Biomol. Chem. 2018, 16, 490. doi: 10.1039/C7OB02892J
13. [13]
  (a) Jinbo, Y.; Kondo, H.; Taguchi, M.; Sakamoto, F.; Tsukamoto, G. J. Org. Chem. 1994, 59, 6057.
  (b) Creary, X.; Losch, A. Org. Lett. 2008, 10, 4975.
  (c) Xu, R. S.; Wan, J. P.; Mao, H.; Pan, Y. J. J. Am. Chem. Soc. 2010, 132, 15531.
  (d) Ge, W. L.; Wei, Y. Y. Green Chem. 2012, 14, 2066.
14. [14]
  Kabalka, G.-W.; Reddy, M.-S.; Yao, M.-L. Tetrahedron Lett. 2009, 50, 7340. doi: 10.1016/j.tetlet.2009.10.061
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