Citation: Shi Dongdong, Bao Hanyang, Xu Zheng, Liu Yunkui. Synthesis of 6-Aryl Phenanthridines via Iron-Catalyzed sp²-C-H Bond Amination/Aromatization Reaction[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1290-1294. doi: 10.6023/cjoc201701054 shu

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

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

Corresponding author: Liu Yunkui, ykuiliu@zjut.edu.cn
Received Date: 30 January 2017
Revised Date: 27 March 2017

Fund Project: Project supported by the National Natural Science Foundation of China 21372201the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology, and the Xin Miao Talents Program of Zhejiang Province 2016R403057Project supported by the National Natural Science Foundation of China 21172197

Figures(1)

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.
- iron catalysis,
- C-H activation,
- amination,
- phenanthridines
1. [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. [2]
  (a) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338. (b) Hartwig Acc. Chem. Res. 2008, 41, 1534.
3. [3]
4. [4]
5. [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. [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. [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. [8]
  Xu, S.; Chen, X.; Li, J.; Xu, W.; Zhang, Y. Chin. J. Org. Chem. 2016, 36, 1985 (in Chinese).
9. [9]
  Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931. doi: 10.1021/ol0711117
10. [10]
  Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500. doi: 10.1021/ja072219k
11. [11]
  Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int. Ed. 2011, 50, 6379. doi: 10.1002/anie.201101943
12. [12]
13. [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. [14]
15. [15]
  Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586.
16. [16]
  Mazzotti, A. R.; Campbell, M. G.; Tang, P.; Murphy, J. M.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 14012. doi: 10.1021/ja405919z
17. [17]
  Michaudel, Q.; Thevenet, D.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 2547. doi: 10.1021/ja212020b
18. [18]
  Su, X.; Yu, S. Chem. Commun. 2016, 52, 10898.
19. [19]
  Chang, M. -Y.; Cheng, Y. -C. Org. Lett. 2016, 18, 1682. doi: 10.1021/acs.orglett.6b00603
20. [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. [21]
  Fernando, P. C.; Scanlan, E. S.; Scottb, J. S.; Walton, J. C. Chem. Commun. 2008, 35, 4189.
22. [22]
  Leardini, R. Synthesis. 1985, 1, 107.
23. [23]
  Peng, J.; Chen, T.; Chen, G.; Li, B. J. Org. Chem. 2011, 76, 9507. doi: 10.1021/jo2017108
1. [1]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
2. [2]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
3. [3]
  Weimei Zeng , Youai Qiu . Electrochemical C-H carboxylation of benzylamines. Chinese Chemical Letters, 2026, 37(1): 111679-. doi: 10.1016/j.cclet.2025.111679
4. [4]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
5. [5]
  Xin Zhou , Zhi Zhang , Yun Yang , Shuijin Yang . A Study on the Enhancement of Photocatalytic Performance in C/Bi/Bi₂MoO₆ Composites by Ferroelectric Polarization: A Recommended Comprehensive Chemical Experiment. University Chemistry, 2024, 39(4): 296-304. doi: 10.3866/PKU.DXHX202310008
6. [6]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
7. [7]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064
8. [8]
  Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
9. [9]
  Xiaofei Zhang , Shanhao Xu , Zhiyuan Wang , Long He , Tiangcheng Huang , Yongming Xu , Yucui Bian , Yike Li , Haijun Chen , Zhongjun Li . Surface doping of graphene into BiOCl for efficient photocatalytic amine coupling under visible light. Acta Physico-Chimica Sinica, 2026, 42(5): 100202-0. doi: 10.1016/j.actphy.2025.100202
10. [10]
  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
11. [11]
  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
12. [12]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
13. [13]
  Yongli Zhao , Dingsheng Cao , Jie-Ping Wan , Yunyun Liu . Synthesis of 3-phosphinyl chromones via in situ iodination mediated C-H phosphination and the tunable synthesis of 2-phosphoryl chromanones. Chinese Chemical Letters, 2026, 37(1): 111740-. doi: 10.1016/j.cclet.2025.111740
14. [14]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
15. [15]
  Wenke ZHENG , Ce LIU , Wei CHEN , Hongshan KE , Fanlong ZENG , Yibo LEI , Anyang LI , Wenyuan WANG . Synthesis and bonding analysis of low-coordinate Fe and Cr complexes with ultra-bulky silylamino groups. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1285-1293. doi: 10.11862/CJIC.20250095
16. [16]
  Bowen Liu , Jianjun Zhang , Han Li , Bei Cheng , Chuanbiao Bie . MOF-derived ZnO/PANI S-scheme heterojunction for efficient photocatalytic phenol mineralization coupled with H₂O₂ generation. Acta Physico-Chimica Sinica, 2025, 41(10): 100121-0. doi: 10.1016/j.actphy.2025.100121
17. [17]
  Xin Zhou , Yiting Huo , Songyu Yang , Bowen He , Xiaojing Wang , Zhen Wu , Jianjun Zhang . Understanding the effect of pH on protonated COF during photocatalytic H₂O₂ production by femtosecond transient absorption spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(12): 100160-0. doi: 10.1016/j.actphy.2025.100160
18. [18]
  Hui Wang , Abdelkader Labidi , Menghan Ren , Feroz Shaik , Chuanyi Wang . Recent Progress of Microstructure-Regulated g-C₃N₄ in Photocatalytic NO Conversion: The Pivotal Roles of Adsorption/Activation Sites. Acta Physico-Chimica Sinica, 2025, 41(5): 100039-0. doi: 10.1016/j.actphy.2024.100039
19. [19]
  Wang Wang , Yucheng Liu , Shengli Chen . Use of NiFe Layered Double Hydroxide as Electrocatalyst in Oxygen Evolution Reaction: Catalytic Mechanisms, Electrode Design, and Durability. Acta Physico-Chimica Sinica, 2024, 40(2): 2303059-0. doi: 10.3866/PKU.WHXB202303059
20. [20]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1356)
HTML views(139)

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

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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