Copper-catalyzed ortho C-H Azidation of Anilines Using Molecular Oxygen as Terminal Oxidant
- Corresponding author: Jiao Ning, jiaoning@pku.edu.cn
Citation: Lin Fengguirong, Liang Yujie, Li Xinyao, Song Song, Jiao Ning. Copper-catalyzed ortho C-H Azidation of Anilines Using Molecular Oxygen as Terminal Oxidant[J]. Acta Chimica Sinica, ;2019, 77(9): 906-910. doi: 10.6023/A19020070
Grieb, P. Philos. Trans. R. Soc. Lond. 1864, 13, 377.
(a) He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451; (b) Xie, F.; Qi, Z.; Li, X. Angew. Chem. Int. Ed. 2013, 52, 11862; (c) Dou, Y.; Xie, Z.; Sun, Z.; Fang, H.; Shen, C.; Zhang, P.; Zhu, Q. ChemCatChem 2016, 8, 3570; (d) Hussain, M. K.; Ansari, M. I.; Kant, R.; Hajela, K. Org. Lett. 2014, 16, 560; (e) Azad, C. S.; Narula, A. K. RSC Adv. 2015, 5, 100223; (f) Yan, Y.-M.; Gao, Y.; Ding, M.-W. Tetrahedron 2016, 72, 5548; (g) Yamamoto, K.; Kamino, S.; Sawada, D. Tetrahedron Lett. 2017, 58, 3936; (h) Dhineshkumar, J.; Gadde, K.; Prabhu, K. R. J. Org. Chem. 2018, 83, 228; (i) Dou, Y.; Yin, B.; Zhang, P.; Zhu, Q. Eur. J. Org. Chem. 2018, 2018, 4571.
Tang, C.; Jiao, N. J. Am. Chem. Soc. 2012, 134, 18924.
doi: 10.1021/ja3089907
Fan, Y.; Wan, W.; Ma, G.; Gao, W.; Jiang, H.; Zhu, S.; Hao, J. Chem. Commun. 2014, 50, 5733.
doi: 10.1039/C4CC01481B
Fang, H.; Dou, Y.; Ge, J.; Chhabra, M.; Sun, H.; Zhang, P.; Zheng, Y.; Zhu, Q. J. Org. Chem. 2017, 82, 11212.
doi: 10.1021/acs.joc.7b01594
(a) Liang, Y.-F.; Wu, K.; Liu, Z.; Wang, X.; Liang, Y.; Liu, C.; Jiao, N. Sci. China Chem. 2015, 58, 1334; (b) Huang, X.; Li, X.; Zou, M.; Song, S.; Tang, C.; Yuan, Y.; Jiao, N. J. Am. Chem. Soc. 2014, 136, 14858; (c) Liang, Y.; Jiao, N. Angew. Chem. Int. Ed. 2016, 55, 4035; (d) Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem. Int. Ed. 2009, 48, 4572; (e) Song, S.; Zhang, Y.; Yeerlan, A.; Zhu, B.; Liu, J.; Jiao, N. Angew. Chem. Int. Ed. 2017, 56, 2487; (f) Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem. Int. Ed. 2011, 50, 11088; (g) Li, X.; Jiao, N. Chin. J. Chem. 2017, 35, 1349.
(a) Zhang, C.; Jiao, N. Angew. Chem. Int. Ed. 2010, 49, 6174; (b) Lu, W.; Xi, C. Tetrahedron Lett. 2008, 49, 4011; (c) Wang, J.; He, J.; Zhi, C.; Luo, B.; Li, X.; Pan, Y.; Cao, X.; Gu, H. RSC Adv. 2014, 4, 16607.
Lin, W.; Zhang, X.; He, Z.; Jin, Y.; Gong, L.; Mi, A. Synth. Commun. 2002, 32, 3279.
doi: 10.1081/SCC-120014032
Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Ruiqing LIU , Wenxiu LIU , Kun XIE , Yiran LIU , Hui CHENG , Xiaoyu WANG , Chenxu TIAN , Xiujing LIN , Xiaomiao FENG . Three-dimensional porous titanium nitride as a highly efficient sulfur host. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 867-876. doi: 10.11862/CJIC.20230441
Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO2 hydrogenation over a Mg-doped In2O3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO2 reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H2 production activity of BaTiO3 nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
Zhaomei LIU , Wenshi ZHONG , Jiaxin LI , Gengshen HU . Preparation of nitrogen-doped porous carbons with ultra-high surface areas for high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 677-685. doi: 10.11862/CJIC.20230404
Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO2 reduction performance of Z-scheme Ag-Cu2O/BiVO4 photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO3 for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO2-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO2 methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276