N,O-双齿螯合作用下铜促进的C-H键直接硝基化反应

doi:10.6023/cjoc201901015

有机化学 ›› 2019, Vol. 39 ›› Issue (6): 1761-1766.DOI: 10.6023/cjoc201901015 上一篇下一篇

所属专题：金属有机化学；碳氢活化合辑2018-2019

研究论文

N,O-双齿螯合作用下铜促进的C-H键直接硝基化反应

王云龙^a, 张林宝^b, 牛俊龙^a, 宋毛平^a

a 郑州大学化学与分子工程学院郑州 450001;
b 青岛科技大学化学与分子工程学院青岛 266042

收稿日期:2019-01-11 修回日期:2019-02-25 发布日期:2019-03-08
通讯作者: 牛俊龙, 宋毛平 E-mail:niujunlong@zzu.edu.cn;mpsong@zzu.edu.cn
基金资助:
国家自然科学基金（Nos.21772179，21672192）和河南省高校科技创新人才计划（No.19HASTIT038）资助项目.

Copper-Promoted Direct Nitration of Arenes Assisted by an N,O-Bidentate Directing System

Wang Yunlong^a, Zhang Linbao^b, Niu Junlong^a, Song Maoping^a

a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
b College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao 266042

Received:2019-01-11 Revised:2019-02-25 Published:2019-03-08
Contact: 10.6023/cjoc201901015 E-mail:niujunlong@zzu.edu.cn;mpsong@zzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772179, 21672192), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 19HASTIT038).

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1. N,O-双齿螯合作用下铜促进的C-H键直接硝基化反应.PDF(9940KB)

摘要/Abstract

以廉价易得的亚硝酸钠为硝基来源，N，O-双齿配体为导向基团，实现了一种廉价铜盐催化的芳烃C-H键的直接硝基化反应.该反应对绝大多数酰胺底物容忍性好，并以中等至良好的收率得到相应的硝基羧酸衍生物，为芳香硝基化合物的合成提供了一种廉价、易操作的方法.

关键词: C-H键活化, 双齿导向, 铜催化, 硝基化

Cu(Ⅱ)-promoted C-H nitration of arenes has been disclosed with the aid of N,O-bidentate directing group. The protocol was operationally simple by using NaNO₂as the nitration source. Various amide substrates were tolerated in the reaction system, which establishes opportunities for developing simple and facile methods, and enriches the strategies to access aromatic nitro derivatives.

Key words: C-H activation, bidentate direction, Cu-catalyzed, nitration

引用此文

王云龙, 张林宝, 牛俊龙, 宋毛平. N,O-双齿螯合作用下铜促进的C-H键直接硝基化反应[J]. 有机化学, 2019, 39(6): 1761-1766.

Wang Yunlong, Zhang Linbao, Niu Junlong, Song Maoping. Copper-Promoted Direct Nitration of Arenes Assisted by an N,O-Bidentate Directing System[J]. Chin. J. Org. Chem., 2019, 39(6): 1761-1766.

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参考文献

[1] (a) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration:Methods and Mechanisms, Wiley-VCH, Weinheim, 1989.
(b) Feuer, H.; Nielsen, A. T. Nitro Compounds:Recent Advances in Synthesis and Chemistry, Wiley-VCH, Weinheim, 1990.
[2] (a) Schofield, K. Aromatic Nitrations, Cambridge University Press, Cambridge, 1980.
(b) Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, Weinheim, 2001.
[3] Hearn, R.; Russell, M. K. R. G. Ann. Rheum. Dis. 1983, 42(Suppl.), 39.
[4] (a) Tani, K.; Lukin, K.; Eaton, P. E. J. Am. Chem. Soc. 1997, 119, 6.
(b) Salzbrunn, S.; Simon, J.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. Synlett 2000, 1485.
(c) Prakash, G. K. S.; Panja, C.; Mathew, T.; Surampudi, V.; Petasis, N. A.; Olah, G. A. Org. Lett. 2004, 6, 2205.
(d) Yan, G.; Yang, M. Org. Biomol. Chem. 2013, 11, 2554.
(e) Das, J. P.; Sinha, P.; Roy, S. Org. Lett. 2002, 4, 3055.
[5] (a) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
(b) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
(c) Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212.
(d) Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
(e) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094.
(f) Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
(g) Misal Castro, L. C.; Chatani, N. Chem. Lett. 2015, 44, 410.
(h) Satoh, T.; Miura, M. Chem. Lett. 2006, 36, 200.
[6] (a) Liu, Y.-K.; Lou, S.-J.; Xu, D.-Q.; Xu, Z.-Y. Chem.-Eur. J. 2010, 13590.
(b) Zhang, W.; Lou, S.; Liu, Y.; Xu, Z. J. Org. Chem. 2013, 78, 5932.
(c) Zhang, L.; Liu, Z.; Li, H.; Fang, G.; Barry, B. D.; Belay, T. A.; Bi, X.; Liu, Q. Org. Lett. 2011, 13, 6536.
(d) Zhang, H.; Zhao, L.; Wang, D.-X.; Wang, M.-X. Org. Lett. 2013, 15, 3836.
(e) Xie, F.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2013, 52, 11862.
(f) Hernando, E.; Castillo, R. R.; Rodriguez, N.; Arrayás, R. G.; Carretero, J. C. Chem. Eur. J. 2014, 20, 13854.
(g) Kianmehr, E.; Nasab, S. B. Eur. J. Org. Chem. 2018, 6447.
(h) Katayev, D.; Pfister, K. F.; Wendling, T.; Gooβen, L. J. Chem.-Eur. J. 2014, 20, 9902.
(i) Liu, J.; Zhuang, S.; Gui, Q.; Chen, X.; Yang, Z.; Tan, Z. Adv. Synth. Catal. 2015, 357, 732.
[7] Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 13154.
[8] Selected examples.
(a) Asako, S.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 17755.
(b) Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030.
(c) Fruchey, E. R.; Monks, B. M.; Cook, S. P. J. Am. Chem. Soc. 2014, 136, 13130.
[9] Selected examples.
(a) Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53, 10209.
(b) Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4684.
(c) Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4688.
(d) Ma, W.; Ackermann, L. ACS Catal. 2015, 5, 2822.
(e) Zhang, L.-B.; Hao, X.-Q.; Zhang, S.-K.; Liu, Z.-J.; Zheng, X.-X.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. Angew. Chem., Int. Ed. 2015, 54, 272.
(f) Zhang, L.-B.; Hao, X.-Q.; Zhang, S.-K.; Zheng, X.-X.; Liu, Z.-J.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. Angew. Chem., Int. Ed. 2015, 54, 10012.
(g) Saxena, P.; Kapur, M. Chem. Asian J. 2018, 13. 861.
[10] Selected examples:
(a) Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898.
(b) Song, W.; Lackner, S.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 2477.
(c) Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 14952.
[11] Selected examples.
(a) Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237.
(b) Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342.
(c) Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043.
(d) Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842.
(e) Shang, M.; Sun, S.-Z.; Wang, H.-L.; Laforteza, B. N.; Dai, H.-X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2014, 53, 10439.
(f) Shang, M.; Wang, H.-L.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 11590.
(g) Li, X.; Liu, Y.-H.; Gu, W.-J.; Li, B.; Chen, F.-J.; Shi, B.-F. Org. Lett. 2014, 16, 3904.
(h) Dong, J.; Wang, F.; You, J. Org. Lett. 2014, 16, 2884.
(i) Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 4457.
(j) Chen, F.-J.; Liao, G.; Li, X.; Wu, J.; Shi, B.-F. Org. Lett. 2014, 16, 5644.
(k) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
(l) Zhang, Q.; Chen, K.; Shi, B.-F. Synlett 2014, 25, 1941.
(m) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
(n) Dou, Y.-D.; Yin, B.; Zhang, P.-F.; Zhu, Q. Eur. J. Org. Chem. 2018, 4571.
(o) Wang, C.-M.; Tang, K.-X.; Gao, T.-H.; Chen, L.; Sun, L.-P. J. Org. Chem. 2018, 83, 8315.
(p) Tu, D.-Q.; Luo, J.; Jiang, C. Chem. Commun. 2018, 54, 2514.
(q) Vinayak, B.; Chandrasekharam, M. Org. Lett. 2017, 19, 3528.
[12] Selected our recent reports:(a) Hao, X.-Q.; Chen, L.-J.; Ren, B.; Li, L.-Y.; Yang, X.-Y.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. Org. Lett. 2014, 16, 1104.
(b) Zhang, L.-B.; Hao, X.-Q.; Zhang, S.-K.; Liu, K.; Ren, B.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. J. Org. Chem. 2014, 79, 10399.
[13] Selected examples.
(a) Wang, D.-W.; Zhao, K.-Y.; Xu, C.-Y.; Miao, H.-Y.; Ding, Y.-Q. ACS Catal. 2014, 4, 3910.
(b) Wang, D.-W.; Ge, B.-Y.; Li, L.; Shan, J.; Ding, Y.-Q. J. Org. Chem. 2014, 79, 8607.
(c) Guo, X-K.; Zhang, L.-B.; Wei, D.-H.; Niu, J.-L. Chem. Sci. 2015, 6, 7059.
(d) Wang, D.-W.; Yu, X.; Yao, W.; Hu, W.-K.; Ge, C.-Y.; Shi, X.-D. Chem.-Eur. J. 2016, 22, 55433.
(e) Yu, X.-L.; Wang, D.-S.; Xu, Z.-J.; Yang, B.-B.; Wang, D.-W. Org. Chem. Front. 2017, 4, 1011.
(f) Wu, Q.; Pan, L.; Du, G.-M.; Zhang, C.; Wang, D.-W. Org. Chem. Front. 2018, 5, 2668.
(g) Xu, Z.-J.; Yu, X.-L.; Sang, X.-X.; Wang, D.-W. Green Chem. 2018, 20, 2571.
(h) Wang, Y.; Du, C.; Wang, Y.-Y.; Guo, X.-K.; Fang, Lei.; Song, M.-P.; Niu, J.-L.; Wei, D.-H. Adv. Synth. Catal. 2018, 360, 2668.
(i) Wang, D.-W.; Yu, X.-L.; Ge, B.-Y.; Miao, H.-Y.; Ding, Y.-Q. Chin. J. Org. Chem. 2015, 35, 676.
(j) Hu, X.-Y.; Yang, B.-B.; Yao, W.; Wang, D.-W. Chin. J. Org. Chem. 2018, 38, 3296.
[14] Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.

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N,O-双齿螯合作用下铜促进的C-H键直接硝基化反应

Copper-Promoted Direct Nitration of Arenes Assisted by an N,O-Bidentate Directing System

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