Synthesis of 6-Aryl Phenanthridines via Iron-Catalyzed sp2-C-H Bond Amination/Aromatization Reaction

doi:10.6023/cjoc201701054

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1290-1294.DOI: 10.6023/cjoc201701054 Previous Articles Next Articles

Notes

铁催化分子内sp²-C-H键的胺化/芳构化反应合成6-芳基菲啶

施冬冬, 鲍汉扬, 徐峥, 刘运奎

浙江工业大学化学工程学院绿色化学与技术国家重点实验室培育基地杭州 310014

收稿日期:2017-01-30 修回日期:2017-03-27 发布日期:2017-03-31
通讯作者: 刘运奎 E-mail:ykuiliu@zjut.edu.cn
基金资助:
国家自然科学基金（Nos.21172197和21372201）、浙江工业大学“省重中之重一级学科”开放基金和浙江省新苗人才计划（No.2016R403057）资助项目.

Synthesis of 6-Aryl Phenanthridines via Iron-Catalyzed sp²-C-H Bond Amination/Aromatization Reaction

Shi Dongdong, Bao Hanyang, Xu Zheng, Liu Yunkui

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2017-01-30 Revised:2017-03-27 Published:2017-03-31
Contact: 10.6023/cjoc201701054 E-mail:ykuiliu@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172197, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology, and the Xin Miao Talents Program of Zhejiang Province (No. 2016R403057).

1. Synthesis of 6-Aryl Phenanthridines via Iron-Catalyzed sp²-C-H Bond Amination/Aromatization Reaction.PDF(1039KB)

Abstract

With FeCl₂ as a catalyst and Selectfluor as an oxidant, an efficient and highly selective synthesis of 6-aryl phenanthridines in one-pot manner has been achieved via an intramolecular sp²-C-H bond amination/aromatization of N-(biphenyl-2-yl(aryl)methyl)benzenesulfonamide derivatives. The optimized reaction conditions were established through systematic investigations of solvents, temperature, catalysts, oxidants and their dosages in the reaction. The present reaction has advantages of simple operation, easy availability of starting materials, the use of inexpensive and low-toxic iron catalyst, and good compatibility of substrates.

Key words: iron catalysis, C-H activation, amination, phenanthridines

Cite this article

Shi Dongdong, Bao Hanyang, Xu Zheng, Liu Yunkui. Synthesis of 6-Aryl Phenanthridines via Iron-Catalyzed sp²-C-H Bond Amination/Aromatization Reaction[J]. Chin. J. Org. Chem., 2017, 37(5): 1290-1294.

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[1] (a) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096.
(b) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 49, 6954.
[2] (a) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
(b) Hartwig Acc. Chem. Res. 2008, 41, 1534.
[3] (a) Guo, X; Li, Z.; Li, C. Prog. Chem. 2010, 22, 1434 (in Chinese). (郭兴伟, 李志平, 李朝军, 化学进展, 2010, 22, 1434.)
(b) Yu, J.; Ding, K. Acta Chim. Sinica 2015, 73, 1223 (in Chinese). (余金权, 丁奎岭, 化学学报, 2015, 73, 1223.)
[4] (a) Xu, H. J.; Man, Q. S.; Lin, Y. C. Chin. J. Org. Chem. 2010, 30, 9 (in Chinese). (许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010, 30, 9.)
(b) Xu, J.; Wei, Z.; Li, J. Chin. J. Org. Chem. 2012, 32, 1208 (in Chinese). (徐娟, 魏真, 李加荣, 有机化学, 2010, 32, 1208.)
(c) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
(d) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
[5] (a) Stuart, D. R.; Laperle, M. B.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474.
(b) Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908.
(c) Li, J. J.; Mei, T. S.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 6452.
[6] (a) Wang, J.; Wang, M.; Chen, K.; Zha, S.; Song, C.; Zhu, J. Org. Lett. 2016, 18, 1178.
(b) Wang, H.; Li, L.; Yu, S.; Li, Y.; Li, X. Org. Lett. 2016, 18, 2914.
[7] (a) Zhang, Z.; Jiang, H.; Huang, Y. Org. Lett. 2014, 16, 5976.
(b) Louillat, M. L.; Patureau, F. W. Org. Lett. 2013, 15, 164.
[8] Xu, S.; Chen, X.; Li, J.; Xu, W.; Zhang, Y. Chin. J. Org. Chem. 2016, 36, 1985 (in Chinese). (徐树英, 陈小佳, 黎吉辉, 许文茸, 张玉苍, 有机化学, 2016, 36, 1985.)
[9] Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931.
[10] Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500.
[11] Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int. Ed. 2011, 50, 6379.
[12] (a) Jia, F.; Li, Z. Org. Chem. Front. 2014, 1, 194.
(b) Alt, I. T.; Plietker, B. Angew. Chem., Int. Ed. 2016, 55, 1519.
(c) Legani, L.; Cerai, G. P.; Morandi, B. ACS Catal. 2016, 6, 8162.
(d) Sun, C.-L.; Li, B. J.; Shi, Z. Chem. Rev. 2011, 111, 1293. (e)Bauer, I.; Knölker, H. J. Chem. Rev. 2015, 115, 3170.
(f) Guo, N.; Zhu, S. Chin. J. Org. Chem. 2015, 35, 1383 (in Chinese). (郭娜, 朱守非, 有机化学, 2015, 35, 1383.)
(g) Zhu, S. F.; Zhou, Q. L. Nat. Sci. Rev. 2014, 1, 580.
[13] (a) Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org. Chem. 2014, 79, 11508.
(b) Zhang, W.; Lou, S.; Liu, Y.; Xu, Z. J. Org. Chem. 2013, 78, 5932.
(c) Zhang, W.; Ren, S.; Zhang, J.; Liu, Y. J. Org. Chem. 2015, 800, 5973.
(d) Wu, D.; Zhang, J.; Cui, J.; Zhang, W.; Liu, Y. Chem. Commun. 2014, 50, 10857.
[14] (a) Ma, L.; Lü, W.; Huang, D.; Niu, T.; Su, Y.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2014, 34, 962 (in Chinese). (马丽芳, 吕文贤, 黄丹凤, 牛腾, 苏瀛鹏, 王克虎, 胡雨来, 有机化学, 2014, 34, 962.)
(b) Krane, B. D.; Fagbule, M. O.; Shamma, M. J. Nat. Prod. 1984, 47, 1.
(c) Bernardo, P. H.; Wan, K. F.; Sivaraman, T.; Xu, J.; Moore, F. K.; Hung, A. W.; Mok, H. Y. K.; Yu, V. C.; Chai, C. L. L. J. Med. Chem. 2008, 51, 6699.
(d) Stevens, N.; O'Connor, N.; Vishwasrao, H.; Samaroo, D.; Kandel, E. R.; Akins, D. L.; Drain, C. M.; Turro, N. J. J. Am. Chem. Soc. 2008, 130, 7182.
[15] Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586.
[16] Mazzotti, A. R.; Campbell, M. G.; Tang, P.; Murphy, J. M.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 14012.
[17] Michaudel, Q.; Thevenet, D.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 2547.
[18] Su, X.; Yu, S. Chem. Commun. 2016, 52, 10898.
[19] Chang, M. -Y.; Cheng, Y. -C. Org. Lett. 2016, 18, 1682.
[20] (a) Tang, E.; Mao, D.; Li, W.; Gao, Z.; Yao, P. Heterocycles 2012, 85, 667.
(b) Kitahara, K.; Toma, T.; Shimokawa, J.; Fukuyama, T. Org. Lett. 2008, 10, 2259.
[21] Fernando, P. C.; Scanlan, E. S.; Scottb, J. S.; Walton, J. C. Chem. Commun. 2008, 35, 4189.
[22] Leardini, R. Synthesis. 1985, 1, 107.
[23] Peng, J.; Chen, T.; Chen, G.; Li, B. J. Org. Chem. 2011, 76, 9507.

铁催化分子内sp²-C-H键的胺化/芳构化反应合成6-芳基菲啶

Synthesis of 6-Aryl Phenanthridines via Iron-Catalyzed sp²-C-H Bond Amination/Aromatization Reaction

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铁催化分子内sp2-C-H键的胺化/芳构化反应合成6-芳基菲啶