Citation: Liu Teng, Liu Jianjun, He Chixian, Cheng Feixiang. Recent Progress on Polyconjugated Nitrodienynes/Nitroenynes:Synthesis and Applications[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2609-2618. doi: 10.6023/cjoc201704024 shu

Recent Progress on Polyconjugated Nitrodienynes/Nitroenynes:Synthesis and Applications

Yunnan Guizhou Plateau Chemical Functional Materials Pollution Control Research Center, Qujing Normal University, Qujing 655011

Corresponding author: Liu Teng, liut_yqzhin@mail.qjnu.edu.cn
Received Date: 13 April 2017
Revised Date: 23 May 2017
Available Online: 2 October 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21261019)the National Natural Science Foundation of China 21261019

Figures(12)

Polyconjugated nitrodienynes/nitroenynes as nitroolefin derivatives are good kind of electrophiles and have been widely used in organic synthesis. There are multiple reaction sites due to the conjugated system. Therefore, competitive reactions of regioselectivity in the reaction process are existence, such as 1, 4-addition reaction, 1, 6-addition reaction, and even 1, 8-addition reaction. The recent progress of the synthesis of nitrodienynes/nitroenynes and their applications in organic synthesis are summarized.
- nitrodienyne,
- nitroenyne,
- organic synthesis application,
- regioselectivity,
- conjugate addition
1. [1]
  (a) Yang, Z.; Liu, J.; Liu, X.; Wang, Z.; Feng, X.; Su, Z.; Hu, C. Adv. Synth. Catal. 2008, 350, 2001.
  (b) Mandal, T.; Zhao, C. Angew. Chem., Int. Ed. 2008, 47, 7714.
  (c) Xue, F.; Zhang, S.; Duan, W.; Wang, W. Adv. Synth. Catal.2008, 350, 2194.
  (d) Gu, Q.; Guo, X.; Wu, X. Tetrahedron 2009, 65, 5265.
  (e) Morris, D. J.; Partridge, A. S.; Manville, C. V.; Racys, D. T.; Woodward, G.; Docherty, G.; Wills, M. Tetrahedron Lett. 2010, 51, 209.
  (f) Peng, L.; Xu, X.; Wang, L.; Huang, J.; Bai, J.; Huang, Q.; Wang, L. Eur.J. Org. Chem. 2010, 1849.
  (g) Lu, A.; Liu, T.; Wu, R.; Wang, Y.; Zhou, Z.; Wu, G.; Fang, J.; Tang, C. Eur.J. Org. Chem. 2010, 5777.
  (h) Lu, A.; Liu, T.; Wu, R.; Wang, Y.; Wu, G.; Zhou, Z.; Fang, J.; Tang, C. J.Org. Chem. 2011, 76, 3872.
  (i) Jiang, X.; Zhang, Y.; Chan, A. S. C.; Wang, R. Org. Lett. 2009, 11, 153.
  (j) Rasappan, R.; Reiser, O. Eur. J. Org. Chem. 2009, 1305.
  (k) Kokotos, C. G.; Kokotos, G. Adv. Synth. Catal. 2009, 351, 1355.
  (l) Li, B.; Wang, Y.; Luo, S.; Zhong, A.; Li, Z.; Du, X.; Xu, D. Eur. J.Org. Chem. 2010, 656.
  (m) Sun, Z.-W.; Peng, F.-Z.; Li, Z.-Q.; Zou, L.-W.; Zhang, S.-X.; Li, X.; Shao, Z.-H. J. Org. Chem. 2012, 77, 4103.
2. [2]
  For selected reviews, see: (a) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
  (b) Almasi, D.; Alonso, D. A.; Najera, C. Tetrahedron: Asymmetry 2007, 18, 299.
  (c) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
  (d) Sulzer-Mosse, S.; Alexakis, A. Chem. Commun. 2007, 3123.
  (e) Vicario, J. L.; Badía, D.; Carrillo, L. Synthesis 2007, 2065.
  (f) Tsakos, M.; Kokotos, C. G. Tetrahedron 2013, 69, 10199.
3. [3]
  (a) Ma, H.; Liu, K.; Zhang, F.-G.; Zhu, C.-L.; Nie, J.; Ma, J.-A. J. Org. Chem. 2010, 75, 1402.
  (b) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas Ⅲ, C. F. Synthesis 2004, 1509.
4. [4]
  Palomo, C.; Vera, S.; Mielgo, A.; Gomez-Bengoa, E. Angew. Chem., Int. Ed. 2006, 45, 5984. doi: 10.1002/(ISSN)1521-3773
5. [5]
  Bonne, D.; Salat, L.; Dulcère, J.-P.; Rodriguez, J. Org. Lett. 2008, 10, 5409. doi: 10.1021/ol8023133
6. [6]
  Corey, E. J.; Zhang, F. Org. Lett. 2000, 2, 4257. doi: 10.1021/ol0068344
7. [7]
  Ballini, R.; Araújo, N.; Gil, M. V.; Román, E.; Serrano J. A. Chem. Rev. 2013, 113, 3493. doi: 10.1021/cr2002195
8. [8]
  Li, X.; Peng, F.; Zhou, M.; Mo, M.; Zhao, R.; Shao, Z. Chem. Commun. 2014, 50, 1745. doi: 10.1039/C3CC48951E
9. [9]
  (a) Sonogashira, K. Metal-Catalyzed Cross-Coupling Reactions, Eds.: Diederich, F.; Stang, P. J., Wiley-VCH, Weinheim, 1997, p. 203.
  (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467.
  (c) Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 2163.
10. [10]
  (a) Akiyama, T.; Takada, K.; Oikawa, T.; Matsuura, N.; Ise, Y.; Okada, S.; Matsunaga, S. Tetrahedron 2013, 69, 6560.
  (b) Iverson, S. L.; Uetrecht, J. P. Chem. Res. Toxicol. 2001, 14, 175.
11. [11]
  (a) Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664.
  (b) Werness, J. B.; Tang, W. Org. Lett. 2011, 13, 3664.
12. [12]
  Sun, Z.; Zhou, M.; Li, X.; Meng, X.; Peng, F.; Zhang, H.; Shao, Z. Chem. Eur. J. 2014, 20, 6112. doi: 10.1002/chem.201400178
13. [13]
  Møller, O.; Steinberg, E. M.; Torssell, K. Acta Chem. Scand., Ser. B 1978, 32, 98.
14. [14]
  (a) Hong, B.; Nimje, R. Y.; Wu, M.; Sadani, A. A. Eur. J.Org. Chem. 2008, 1449.
  (b) Wang, Y.; Luo, Y.; Zhang, H.; Xu, P. Org. Biomol. Chem.2012, 10, 8211.
  (c) Li, G.; Xie, J.; Hou, J.; Zhu, S.; Zhou, Q. Adv. Synth. Catal.2013, 355, 1597.
15. [15]
  Evans, D. A.; Mito, S.; Seidel, D. J. Am. Chem. Soc. 2007, 129, 11583. doi: 10.1021/ja0735913
16. [16]
  Meng, X.-L.; Liu, T.; Sun, Z.-W.; Wang, J.-C.; Peng, F.-Z.; Shao, Z.-H. Org. Lett. 2014, 16, 3044. doi: 10.1021/ol501158b
17. [17]
  Liu, T.; Zhou, M.; Yuan, T.; Fu, B.; Wang, X.; Peng, F.; Shao, Z. Adv. Synth. Catal. 2017, 359, 89. doi: 10.1002/adsc.v359.1
18. [18]
  (a) Tsakos, M.; Kokotos, C. G.; Kokotos, G. Adv. Synth.Catal. 2012, 354, 740.
  (b) Flores-Ferrándiz, J.; Stiven, A.; Sotorríos, L.; Glmez-Bengoa, E.; Chinchilla, R. Tetrahedron: Asymmetry2015, 26, 970.
19. [19]
  (a) Hénon, H.; Mauduit, M.; Alexakis, A. Angew. Chem., Int. Ed. 2008, 47, 9122.
  (b) Tian, X.; Liu, Y.-K.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 6439.
20. [20]
  Ganesh, M.; Namboothiri, I. N. N. Tetrahedron 2007, 63, 11973. doi: 10.1016/j.tet.2007.09.012
21. [21]
  Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 48, 8923. doi: 10.1002/anie.v48:47
22. [22]
  Belot, S.; Quintard, A.; Krause, N.; Alexakis, A. Adv. Synth. Catal. 2010, 352, 667. doi: 10.1002/adsc.v352:4
23. [23]
  (a) Tissot, M.; Müller, D.; Belot, S.; Alexakis, A. Org. Lett. 2010, 12, 2770.
  (b) Tissot, M.; Alexakis, A. Chem. Eur. J. 2013, 19, 11352.
24. [24]
  Li, X.-J.; Peng, F.-Z.; Li, X.; Wu, W.-T.; Sun, Z.-W.; Li, Y.-M.; Zhang, S.-X.; Shao, Z.-H. Chem.-Asian J. 2011, 6, 220. doi: 10.1002/asia.201000561
25. [25]
  Uraguchi, D.; Kinoshita, N.; Kizu, T.; Ooi, T. Synlett 2011, 9, 1265.
26. [26]
  Li, X.; Li, X.; P. F.; Shao, Z. Adv. Synth. Catal. 2012, 354, 2873. doi: 10.1002/adsc.v354.14/15
27. [27]
  Maji, B.; Ji, L.; Wang, S.; Vedachalam, S.; Ganguly, R.; Liu, X.-W. Angew. Chem., Int. Ed. 2012, 51, 8276. doi: 10.1002/anie.v51.33
28. [28]
  Bharathiraja, G.; Sakthivel, S.; Sengoden, M.; Punniyamurthy, T. Org. Lett. 2013, 15, 4996. doi: 10.1021/ol402305b
29. [29]
  Cao, Z.-Y.; Zhao, Y.-L.; Zhou, J. Chem. Commun. 2016, 52, 2537. doi: 10.1039/C5CC10096H
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