Chinese Journal of Organic Chemistry >
Recent Advances in Transition-Metal-Catalyzed Directing Group Assisted Nitration of Inert C-H Bonds
Received date: 2018-07-01
Revised date: 2018-08-29
Online published: 2018-09-26
Supported by
Project supported by the Maoming City Technology Bureau (No. 917313), the Guangdong University of Petrochemical Technology (Nos. 517152、517136、201711656024).
Aromatic nitro compounds are of great importance as chemical raw materials and organic synthesis intermediates. Traditional electrophilic nitration is difficult to achieve regioselective nitrification. In recent years, transition-metal-catalyzed C-H bond activation has developed rapidly. Most functional groups can be introduced into specific sites of aromatics through the chelation of transition metals with directing groups. Directing-group assisted C-H nitration, which is catalyzed by palladium, rhodium, ruthenium and other transition-metal, has made important progress due to its less byproducts, good regioselectivity and environmental protection. According to different transition metal catalysts, the research progress on transition-metal-catalyzed directing-group assisted C-H nitration is summarized, and the limitations of the research field and prospects for future develop-ment are presented.
Cheng Huicheng , Lin Jinlong , Zhang Yaofeng , Chen Bing , Wang Min , Cheng Lihua , Ma Jiaoli . Recent Advances in Transition-Metal-Catalyzed Directing Group Assisted Nitration of Inert C-H Bonds[J]. Chinese Journal of Organic Chemistry, 2019 , 39(2) : 318 -327 . DOI: 10.6023/cjoc201807002
[1] (a) Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
(b) Feuer, H.; Nielson, A. T. Nitro Compounds:Recent Advances in Synthesis and Chemistry, VCH, New York, 1990.
(c) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration:Methods and Mechanisms, VCH, Weinheim, 1989.
[2] White, E. Org. Synth. 1973, 47, 44.
[3] For review on synthesis of nitro compounds, see:Yan, G.; Yang, M. Org. Biomol. Chem. 2013, 11, 2554.
[4] Prakash, G. K.; Mathew, T. Angew. Chem., Int. Ed. 2010, 49, 1726.
[5] For reviews on ortho CAr-H activation, see:(a) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(b) Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
(c) Liu, C.; Zhang, H.; Shi, W.; Lei, A. W. Chem. Rev. 2011, 111, 1780.
(d) Davies, H. L.; Bois, J. D.; Yu, J. Q. Chem. Soc. Rev. 2011, 40, 1855.
(e) Li, B. J.; Shi, Z. J. Chem. Soc. Rev. 2012, 41, 5588.
(f) Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936.
(g) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.
(h) Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814.
(i) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788.
(j) Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936.
(k) Li, B.; Dixneuf, P. H. Chem. Soc. Rev. 2013, 42, 5744.
(l) Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
(m) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
(n) Moselage, M.; Li, J.; Ackermann, L. ACS Catal. 2016, 6, 498.
(o) Wang, Y.; Chen, G.; Cui, X. Chin. J. Org. Chem. 2012, 32, 2018(in Chinese). (王勇, 程国林, 崔秀灵, 有机化学, 2012, 32, 2018.)
(p)Zhang, W.; Zhang, J.; Liu, Y. Chin. J. Org. Chem. 2014, 34, 36(in Chinese). (张巍, 张家慧, 刘运奎, 有机化学, 2014, 34, 36.)
(r) Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487(in Chinese). (张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
(s) Tang, H. M.; Huo, X. H.; Meng, Q. H.; Zhang, W. B. Acta Chim. Sinica 2016, 74, 219(in Chinese). (汤淏溟, 霍小红, 孟庆华, 张万斌, 化学学报, 2016, 74, 219.)
[6] Liu, Y.-K.; Lou, S.-J.; Xu, D.-Q.; Xu, Z.-Y. Chem.-Eur. J. 2010, 16, 13590.
[7] Zhang, W.; Lou, S.; Liu, Y.; Xu, Z. J. Org. Chem. 2013, 78, 5932.
[8] Zhang, W.; Wu, D.; Zhang, J.; Liu, Y. Eur. J. Org. Chem. 2014, 26, 5827.
[9] Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org. Chem. 2014, 79, 11508.
[10] Zhang J.; Zhang, W.; Ren, S.; Cui, J.; Liu, Y. Chin. J. Org. Chem. 2015, 35, 647.
[11] Dong, J.; Jin, B.; Sun, P. Org. Lett. 2014, 16, 4540.
[12] Majhi, B.; Kundu, D.; Ahammed, S.; Ranu, B. C. Chem.-Eur. J. 2014, 20, 9862.
[13] Liang, Y.-F.; Li, X.; Wang, X. C.; Yan, Y.; Feng, P.; Jiao, N. ACS Catal. 2015, 5, 1956.
[14] Zhang, W.; Ren, S.; Zhang, J.; Liu, Y. J. Org. Chem. 2015, 80, 5973.
[15] Qiao, H.-J.; Yang, F.; Wang, S.-W.; Leng, Y.-T.; Wu, Y.-J. Tetrahedron 2015, 71, 9258.
[16] Lu, Y.; Li, Y.; Zhang, R.; Jin, K.; Duan, C. Tetrahedron 2013, 69, 9422.
[17] Feng, Y. S.; Mao, L.; Bu, X. S.; Dai, J. J.; Xu, H. J. Tetrahedron 2015, 71, 3827.
[18] Pawar, G. G.; Brahmanandan, A.; Kapur, M. Org. Lett. 2016, 18, 448.
[19] Zhao, F.; Chen, Z.; Huang, S. J.; Jiang, Y. B. Synthesis 2016, 48, 2105.
[20] Chang, M.; Chen, H.; Wang, H. J. Org. Chem. 2017, 82, 10601.
[21] Zhang, L.; Liu, Z.; Li, H.; Fang, G.; Barry, B.-D.; Belay, T. A.; Bi, X.; Liu, Q. Org. Lett. 2011, 13, 6536.
[22] Zhang, H.; Zhao, L.; Wang, D. Org. Lett. 2013, 15, 3836.
[23] Katayev, D.; Pfister, K. F.; Wendling, T.; Goolßen, L. J. Chem.-Eur. J. 2014, 20, 9902.
[24] Liu, J.; Zhuang, S.; Gui, Q.; Chen, X.; Yang, Z.; Tan, Z. Adv. Synth. Catal. 2015, 357, 732.
[25] Hernando, E.; Rafael, R.; Castillo, R. R; Rodrguez, N. Chem.-Eur. J. 2014, 20, 13854.
[26] Sadhu, P.; Alla, S. K.; Punniyamurthy, T. J. Org. Chem. 2015, 80, 8245.
[27] Ji, Y.-F.; Yan, H.; Jiang, Q.-B. Eur. J. Org. Chem. 2015, 2051.
[28] He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054.
[29] Zhu, X.; Qiao, L.; Ye, P.; Ying, B.; Xu, J.; Shen, C.; Zhang, P. RSC Adv. 2016, 6, 89979.
[30] Planas, O.; Company, A.; Ribas, X. Adv. Synth. Catal. 2016, 358, 1679.
[31] Khan, B.; Khan, A. A.; Bora, D.; Verma, D.; Koley, D. Chemis-trySelect 2017, 2, 260.
[32] Wang, Y.; Yu, F.; Han, X.; Li, M.; Tong, Y.; Ding, J.; Hou, H. Inorg. Chem. 2017, 56, 5953.
[33] Vinayak, B.; Chandrasekharam, M. Org. Lett. 2017, 19, 3528.
[34] Vinayak, B.; Ashok, A.; Chandrasekharam, M. Eur. J. Org. Chem. 2017, 7127.
[35] Reddy, G. M.; Rao, N. S.; Sarma, M. H. Asian J. Org. Chem. 2017, 6, 59.
[36] Tu, D.; Luo, J.; Jiang, C. Chem. Commun. 2018, 54, 2514.
[37] Wang, C. M.; Tang, K. X.; Gao, T. H.; Chen, L.; Sun, L. P. J. Org. Chem. 2018, 83, 8315.
[38] Fan, Z.; Ni, J.; Zhang, A. J. Am. Chem. Soc. 2016, 138, 8470.
[39] Fan, Z.; Li, J.; Lu, H.; Wang, D.-Y.; Wang, C.; Uchiyama, M.; Zhang, A. Org. Lett. 2017, 19, 3199.
[40] Fan, Z.; Lu H.; Zhang, A. J. Org. Chem. 2018, 83, 3245.
[41] Xie, F.; Qi, Z. S.; Li, X. W. Angew. Chem., Int. Ed. 2013, 52, 11862.
[42] Rao, D. N.; Rasheed, S. K.; Raina, G.; Ahmed, Q. N.; Jaladanki, C. K.; Bharatam, P. V.; Das, P. J. Org. Chem. 2017, 82, 7234.
[43] Saxena, P.; Kapur, M. Chem. Asian J. 2018, 13, 861.
[44] Wan, L.; Qiao, K.; Yuan X.; Zheng, M.-W.; Fan, B.-B.; Di, Z. C.; Zhang, D.; Fang, Z.; Gu, K. Adv. Synth. Catal. 2017, 359, 2596
[45] Botla, V.; Ramana, D. V.; Chiranjeevi, B.; Chandrasekharam, M. ChemistrySelect 2016, 1, 3974.
[46] Gao, Y.; Mao, Y.; Zhang, B.; Zhan, Y.; Huo, Y. Org. Biomol. Chem. 2018, 16, 3881.
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