Citation: Wang Shaofan, Zhao Qipeng, Wang Guodong, Wang Kai, Xia Chengcai. Palladium-Catalyzed Direct o-Nitrification of Azobenzenes with Co(NO₃)₂·6H₂O via C-H Activation[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1849-1854. doi: 10.6023/cjoc201711041 shu

Palladium-Catalyzed Direct o-Nitrification of Azobenzenes with Co(NO₃)₂·6H₂O via C-H Activation

a.
School of Pharmacy, Ningxia Medical University, Yinchuan 750004
b.
Pharmacy College, Taishan Medical University, Tai'an 271016

Corresponding author: Xia Chengcai, xiachc@163.com
Received Date: 22 November 2017
Revised Date: 28 January 2018
Available Online: 8 July 2018
Fund Project: the Projects of Medical and Health Technology Development Program in Shandong Province 2015WS0102Project supported by the Projects of Medical and Health Technology Development Program in Shandong Province (No. 2015WS0102)

Figures(2)

An efficient protocol for conversion of azobenzenes into their ortho-nitro derivatives via palladium-catalyzed C-H bond activation has been developed. Commercially available and less expensive Co(NO₃)₂·6H₂O was used as the nitrification reagent. Various o-nitroazobenzenes were obtained in excellent yields.
- C-H activation,
- azobenzenes,
- Co(NO₃)₂·6H₂O,
- nitrification
1. [1]
  (a) Ballini, R. ; Barboni, L. ; Fringuelli, F. ; Palmieri, A. ; Pizzo F. ; Vaccaro, L. Green Chem. 2007, 9, 823.
  (b) Papadopoulou, M. V. ; Trunz, B. B. ; Bloomer, W. D. ; McKenzie, C. ; Wilkinson, S. R. ; Prasittichai, C. ; Brun, R. ; Kaiser, M. ; Torreele, E. J. Med. Chem. 2011, 54, 8214.
  (c) Hou, W. D. ; Wei, Q. ; Liu, G. S. ; Chen, J. ; Guo, J. ; Peng, Y. G. Org. Lett. 2015, 17, 4870.
2. [2]
  (a) Prakash, G. K. S. ; Panja, C. ; Mathew, T. ; Surampudi, V. ; Petasis, N. A. ; Olah, G. A. Org. Lett. 2004, 6, 2205.
  (b) Manna, S. ; Maity, S. ; Rana, S. ; Agasti, S. ; Maiti, D. Org. Lett. 2012, 14, 1736.
3. [3]
  Natarajan, P.; Chaudhary, R.; Venugopalan, P. J. Org. Chem. 2015, 80, 10498. doi: 10.1021/acs.joc.5b02133
4. [4]
  (a) Fors, B. P. ; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 12898.
  (b) Yan, G. B. ; Yang, M. H. Org. Biomol. Chem. 2013, 11, 2554.
5. [5]
  (a) Liu, Y. K. ; Lou, S. J. ; Xu, D. Q. ; Xu, Z. Y. Chem. -Eur. J. 2010, 16, 13590.
  (b) Zhang, L. ; Liu, Z. H. ; Li, H. Q. ; Fang, G. C. ; Barry, B. D. ; Belay, T. A. ; Bi, X. H. ; Liu, Q. Org. Lett. 2011, 13, 6536.
  (c) Zhang, W. ; Lou, S. J. ; Liu, Y. K. ; Xu, Z. Y. J. Org. Chem. 2013, 78, 5932.
  (d) Katayev, D. ; Pfister, K. F. ; Wendling, T. ; Gooßen, L. J. Chem. -Eur. J. 2014, 20, 9902.
6. [6]
  (a) Kilpatrick, B. ; Heller, M. ; Arns, S. Chem. Commun. 2013, 49, 514.
  (b) Majhi, B. ; Kundu, D. ; Ahammed, S. ; Ranu, B. C. Chem. -Eur. J. 2014, 20, 9862.
  (c) Liang, Y. F. ; Li, X. Y. ; Wang, X. Y. ; Yan, Y. P. ; Feng, P. ; Jiao, N. ACS Catal. 2015, 5, 1956.
  (d) Zhang, W. ; Ren, S. B. ; Zhang, J. ; Liu, Y. K. J. Org. Chem. 2015, 80, 5973.
7. [7]
  Dong, J. W.; Jin, B.; Sun, P. P. Org. Lett. 2014, 16, 4540. doi: 10.1021/ol502090n
8. [8]
  Lu, Y.; Li, Y. M.; Zhang, R.; Jin, K.; Duan, C. Y. Tetrahedron 2013, 69, 9422. doi: 10.1016/j.tet.2013.08.076
9. [9]
  Sadhu, P.; Alla, S. K.; Punniyamurthy, T. J. Org. Chem. 2015, 80, 8245. doi: 10.1021/acs.joc.5b01021
10. [10]
  (a) Banghart, M. R. ; Mourot, A. ; Fortin, D. L. ; Yao, J. Z. ; Kramer, R. H. ; Trauner, D. Angew. Chem., Int. Ed. 2009, 48, 9097.
  (b) Takahashi, H. T. ; Ishioka, T. ; Koiso, Y. ; Sodeoka, M. ; Hashimoto, Y. Biol. Pharm. Bull. 2000, 23, 1387.
11. [11]
  Roy, D.; Fragiadakis, D.; Roland, C. M.; Dabrowski, R.; Dziaduszek J.; Urban, S. J. Chem. Phys. 2014, 140, 530.
12. [12]
  (a) Ferri, V. ; Elbing, M. ; Pace, G. ; Dickey, M. D. ; Zharnikov, M. ; Samor, P. ; Mayor, M. ; Rampi, M. A. Angew. Chem., Int. Ed. 2008, 47, 3407.
  (b) Puntoriero, F. ; Ceroni, P. ; Balzani, Vi. ; Bergamini, G. ; Vögtle, F. J. Am. Chem. Soc. 2007, 129, 10714.
13. [13]
  Chang, C. W.; Lu, Y. C.; Wang, T. T.; Diau, E. W. G. J. Am. Chem. Soc. 2004, 126, 10109. doi: 10.1021/ja049215p
14. [14]
  (a) Zarei, A. ; Hajipour, A. R. ; Khazdooz, L. ; Mirjalili, B. F. ; Chermahini, A. N. Dyes Pigm. 2009, 81, 240.
  (b) Bafana, A. ; Devi, S. S. ; Chakrabarti, T. Environ. Rev. 2011, 19, 350.
15. [15]
  Feringa, B. L.; Delden, R. A. V.; Koumura, N.; Geertsema, E. M. Chem. Rev. 2000, 100, 1789. doi: 10.1021/cr9900228
16. [16]
  (a) Jones, P. ; Altamura, S. ; Boueres, J. ; Ferrigno, F. ; Fonsi, M. ; Giomini, C. ; Lamartina, S. ; Monteagudo, E. ; Ontoria, J. M. ; Orsale, M. V. ; Palumbi, M. C. ; Pesci, S. ; Roscilli, G. ; Scarpelli, R. ; Fademrecht, C. S. ; Toniatti, C. ; Rowley, M. J. Med. Chem. 2009, 52, 7170.
  (b) Loddo, R. ; Novelli, F. ; Sparatore, A. ; Tasso, B. ; Tonelli, M. ; Boido, V. ; Sparatore, F. ; Collu, G. ; Delogu, I. ; Giliberti, G. ; Colla, P. L. Bioorg. Med. Chem. 2015, 23, 7024.
  (c) Nykaza, T. V. ; Harrison, T. S. ; Ghosh, A. ; Putnik, R. A. ; Radosevich, A. T. J. Am. Chem. Soc. 2017, 139, 6839.
17. [17]
  (a) Bellotto, S. ; Reuter, R. ; Heinis, C. ; Wegner, H. A. J. Org. Chem. 2011, 76, 9826.
  (b) Bandara, H. M. D. ; Friss, T. R. ; Enriquez, M. M. ; Isley, W. ; Incarvito, C. ; Frank, H. A. ; Gascon, J. ; Burdette, S. C. J. Org. Chem. 2010, 75, 4817.
18. [18]
  Hofmann, K.; Brumm, S.; Mende, C.; Nagel, K.; Seifert, A.; Roth, I.; Schaarschmidt, D.; Lang, H.; Spange, S. New J. Chem. 2012, 36, 1655. doi: 10.1039/c2nj40313g
19. [19]
  (a) Cantillo, D. ; Baghbanzadeh, M. ; Kappe, C. O. Angew. Chem., Int. Ed. 2012, 51, 10190.
  (b) Shi, Q. ; Lu, R. ; Jin, K. ; Zhang, Z. ; Zhao, D. Green Chem. 2006, 8, 868.
  (c) Vass, A. ; Dudas, J. ; Toth, J. ; Varma, R. S. Tetrahedron Lett. 2001, 42, 5347.
20. [20]
  (a) Nguyen, T. B. ; Ermolenko, L. ; Al-Mourabit, A. J. Am. Chem. Soc. 2012, 135, 118.
  (b) Kim, J. ; Kim, J. ; Lee, H. ; Lee, B. M. ; Kim, B. H. Tetrahedron 2011, 67, 8027.
21. [21]
  (a) Xia, C. C. ; Wei, Z. J. ; Yang, Y. ; Yu, W. B. ; Liao, H. X. ; Shen, C. ; Zhang, P. F. Chem. -Asian J. 2016, 11, 360.
  (b) Shen, H. Y. ; Shen, C. ; Wang, A. M. ; Zhang, P. F. Catal. Sci. Technol. 2015, 5, 2065.
  (c) Xia, C. C. ; Wei, Z. J. ; Shen, C. ; Xu, J. ; Yang, Y. ; Su, W. K. ; Zhang, P. F. RSC Adv. 2015, 5, 52588.
  (d) Xia, C. C. ; Wang, K. ; Xu, J. ; Wei, Z. J. ; Shen, C. ; Duan, G. Y. ; Zhu, Q. ; Zhang, P. F. RSC Adv. 2016, 6, 37173.
  (e) Xia, C. C. ; Wang, K. ; Xu, J. ; Shen, C. ; Sun, D. ; Li, H. S. ; Wang, G. D. ; Zhang, P. F. Org. Biomol. Chem. 2017, 15, 531.
  (f) Fu, X. P. ; Wei, Z. J. ; Xia, C. C. ; Shen, C. ; Xu, J. ; Yang, Y. ; Wang, K. ; Zhang, P. F. Catal. Lett. 2017, 147, 400.
22. [22]
  Rosevear, J.; Wilshire, J. F. K. Aust. J. Chem. 1987, 40, 1663. doi: 10.1071/CH9871663
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Palladium-Catalyzed Direct o-Nitrification of Azobenzenes with Co(NO3)2·6H2O via C-H Activation

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通讯作者: 陈斌, bchen63@163.com

Palladium-Catalyzed Direct o-Nitrification of Azobenzenes with Co(NO₃)₂·6H₂O via C-H Activation