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
1. [1]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
2. [2]
  Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574
3. [3]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
4. [4]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
5. [5]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
6. [6]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
7. [7]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
8. [8]
  Qiao Song , Xue Peng , Zhouyu Wang , Leyong Wang . Iron-catalyzed C–H activation: A sustainable approach to efficient organic synthesis. Chinese Chemical Letters, 2025, 36(5): 110869-. doi: 10.1016/j.cclet.2025.110869
9. [9]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
10. [10]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
11. [11]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
12. [12]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
13. [13]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
14. [14]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
15. [15]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
16. [16]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
17. [17]
  Huirong Chen , Yingzhi He , Yan Han , Jianbo Hu , Jiantang Li , Yunjia Jiang , Basem Keshta , Lingyao Wang , Yuanbin Zhang . A new SIFSIX anion pillared cage MOF with crs topological structure for efficient C2H2/CO2 separation. Chinese Journal of Structural Chemistry, 2025, 44(2): 100508-100508. doi: 10.1016/j.cjsc.2024.100508
18. [18]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
19. [19]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
20. [20]
  Jinpeng Du , Junlin Chen , Yulong Shan , Tongliang Zhang , Yu Sun , Zhongqi Liu , Xiaoyan Shi , Wenpo Shan , Yunbo Yu , Hong He . Insight into the effects of C₃H₆ on fresh and hydrothermally aged Cu-SSZ-39 catalysts. Chinese Chemical Letters, 2025, 36(3): 110019-. doi: 10.1016/j.cclet.2024.110019

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(990)
HTML views(100)

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

Metrics

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