Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines
- Corresponding author: Hao Wenyan, wenyanhao@jxnu.edu.cn
Citation:
Hao Wenyan, Wang Yuyun, Liu Yunyun. Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines[J]. Chinese Journal of Organic Chemistry,
;2017, 37(12): 3198-3203.
doi:
10.6023/cjoc201705041
(a) Solomon, V. R. ; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
(b) Liu, G. ; Yi, M. ; Liu, L. ; Wang, J. ; Wang, J. Chem. Commun. 2015, 51, 2911.
Wan, J.; Y. Jing, Y.; Wei, L. Asian J. Org. Chem. 2017, 6, 668.
Gharpure, S. J.; Nanda, S. K.; Adate, P. A.; Shelke, Y. G. J. Org. Chem. 2017, 82, 2067.
doi: 10.1021/acs.joc.6b02896
Ali, W.; Dahiya, A.; Pandey, R.; Alam, T.; Patel, B. K. J. Org. Chem. 2017, 82, 2089.
doi: 10.1021/acs.joc.6b02912
Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
doi: 10.1021/ja9053509
Sun, K.; Lv, Y.; Wang, J.; Sun, J.; Liu, L.; Jia, M.; Liu, X.; Z. Li, Z.; Wang, X. Org. Lett. 2015, 17, 4408.
doi: 10.1021/acs.orglett.5b01857
Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
doi: 10.1021/ja8059396
Boudet, N.; Lachs, J. R.; Knochel, P. Org. Lett. 2007, 9, 5525.
doi: 10.1021/ol702494k
(a) Cong, X. ; Zeng, X. Org. Lett. 2014, 16, 3716.
(b) Reddy, M. D. ; Fronczek, F. R. ; Watkins, E. B. Org. Lett. 2016, 18, 5620.
(c) Chen, H. ; Li, P. ; Wang, M. ; Wang, L. Org. Lett. 2016, 18, 4794.
(d) Kuninobu, Y. ; Nishia, M. ; Kanai, M. Org. Biomol. Chem. 2016, 14, 8092.
(e) Shen, C. ; Xu, J. ; Beibei Ying, B. ; Zhang, P. ChemCatChem 2016, 8, 3557.
(f) Zhang, J. ; Hao, X. ; Wang, Z. ; Ren, C. ; Niu, J. ; Song, M. Chin. J. Org. Chem. 2017, 37, 1237.
(g) Luo, F. ; Long, Y. ; Li, Z. ; Zhou, X. Acta Chim. Sinica 2016, 74, 805.
(a) Ji, D. ; He, X. ; Xu, Y. ; Xu, Z. ; Bian, Y. ; Liu, W. ; Zhu, Q. ; Xu, Y. Org. Lett. 2016, 18, 4478.
(b) Whiteoak, C. J. ; Planas, O. ; Company, A. ; Ribasa, X. Adv. Synth. Catal. 2016, 358, 1679.
(c) He, Y. ; Zhao, N. ; Qiu, L. ; Zhang, X. ; Fan, X. Org. Lett. 2016, 18, 6054.
(d) Dou, Y. ; Xie, Z. ; Sun, Z. ; Fang, H. ; Shen, C. ; Zhang, P. ; Qing Zhu, Q. ChemCatChem 2016, 8, 3570.
(e) Sahoo, H. ; Kesava, M. ; Ramakrishna, R. ; Baidya, M. Chem. -Eur. J. 2016, 22, 1592.
(a) Liang, H. ; Jiang, K. ; Ding, W. ; Yuan, Y. ; Shuai, Li. ; Chen, Y. ; Ye Wei, Y. Chem. Commun. 2015, 51, 16928.
(b) Qiao, H. ; Sun, S. ; Yang, F. ; Zhu, Y. ; Zhu, W. ; Dong, Y. ; Wu, Y. ; Kong, X. ; Jiang, L. ; Wu, Y. Org. Lett. 2015, 17, 6086.
(c) Wei, J. ; Jiang, J. ; Xiao, X. ; Lin, D. ; Deng, Y. ; Ke, Z. ; Jiang, H. ; Zeng, W. J. Org. Chem. 2016, 81, 946.
(d) Xu, J. ; Shen, C. ; Zhu, X. ; Zhang, P. ; Ajitha, M. J. ; Huang, K. ; An, Z. ; Liu, X. Chem. Asian J. 2016, 11, 882.
(e) Zhu, L. ; Qiu, R. ; Cao, X. ; Xiao, S. ; Xu, X. ; Au, C. ; Yin, S. Org. Lett. 2015, 17, 5528.
(a) Suess, A. M. ; Mehmed Z. Ertem, M. Z. ; Cramer, C. J. Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
(b) Guo, H. ; Chen, M. ; Jiang, P. ; Chen, J. ; Pan, L. ; Wang, M. ; Xie, C. ; Zhang, Y. Tetrahedron 2015, 71, 70.
(c) Liu, X. ; Wu, Z. ; Luo, X. ; He, Y. ; Zhou, X. ; Fan, Y. ; Huang, G. RSC Adv. 2016, 6, 71485.
(d) Xu, J. ; Zhu, X. ; Zhou, G. ; Ying, B. ; Ye, P. ; Su, L. ; Shen, C. ; Zhang, P. Org. Biomol. Chem. 2016, 14, 3016.
(e) Khan, B. ; Ruchir Kant, R. ; Koley, D. Adv. Synth. Catal. 2016, 358, 2352.
(f) Wu, C. ; Zhou, H. ; Wu, Q. ; He, M. ; Li, P. ; Su, Q. ; Mu, Y. Synlett. 2016, 27, A~H.
(g) Sahoo, H. ; Ramakrishna, I. ; Baidya, M. Chem. Select 2016, 1, 1949.
(h) He, X. ; Xu, Y. ; Kong, L. ; Wu, H. ; Ji, D. ; Wang, Z. ; Xu, Y. ; Zhu, Q. Org. Chem. Front. 2017, 4, 1046.
(i) Rao, N. S. ; Reddy, G. M. ; Sridhar, B. ; Sarma, M. S. Eur. J. Org. Chem. 2017, 438.
Sun, M.; Sun, S.; Qiao, H.; Yang, F.; Zhu, Y.; Kang, J.; Wu, Y.; Wu, Y. Org. Chem. Front. 2016, 3, 1646.
doi: 10.1039/C6QO00379F
Xia, C.; Wang, K.; Xu, J.; Shen, C.; Sun, D.; Li, H.; Wang, G.; Zhang, P. Org. Biomol. Chem., 2017, 15, 531.
doi: 10.1039/C6OB02375D
(a) Abouelhassan, Y. ; Garrison, V. G. ; Burch, M. ; Wong, W. ; Norwood, V. M. ; Huigens, R. W. Bioorg. Med. Chem. Lett. 2014, 24, 5076.
(b) Liu, Y. -C. ; Wei, J. -H. ; Chen, Z. -F. ; Liu, M. ; Gu, Y. -Q. ; Huang, K. -B. ; Li, Z. -Q. ; Liang, H. Eur. J. Med. Chem. 2013, 69, 554.
(c) Tardito, S. ; Barilli, A. ; Bassanetti, I. ; Tegoni, M. ; Bussolati, O. ; Franchi-Gazzola, R. ; Mucchino, C. ; Marchio, L. J. Med. Chem. 2012, 55, 10448.
(d) Bhat, S. ; Shim, J. S. ; Zhang, F. ; Chong, C. R. ; Liu, J. O. Org. Biomol. Chem. 2012, 10, 2979.
(e) Madrid, P. B. ; Sherrill, J. ; Liou, A. P. ; Weisman, J. L. ; Derisi, J. L. ; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015.
(a) Jiang, H. ; Taggart, H. ; Zhang, X. ; Benbrook, D. M. ; Lind, S. E. ; Ding, W. -Q. Cancer Lett. 2011, 312, 11.
(b) Heidary, D. K. ; Howerton, B. S. ; Glazer, E. C. J. Med. Chem. 2014, 57, 8936.
During the preparation of our manuscript, a water-mediated C5-H halogenations of 8-amidoquinolines has been reported. Chen, J. ; Wang, T. ; Liu, Y. ; Wang, T. ; Lin, A. ; Yao, H. ; Xu, J. Org. Chem. Front. 2017, 4, 622.
Hao, W.-Y.; Liu, Y.-Y. Beilstein J. Org. Chem. 2015, 11, 2132.
doi: 10.3762/bjoc.11.230
Menini, L.; da Cruz Santos, J. C.; Gusevskaya, E. V. Adv. Synth. Catal. 2008, 350, 2052.
doi: 10.1002/adsc.v350:13
Wang, Y.; Wang, Y.; Jiang, K.; Zhang, Q.; Li, D. Org. Biomol. Chem. 2016, 14, 10180.
doi: 10.1039/C6OB02079H
Qiao, H. J.; Sun, S. Y.; Yang, F.; Zhu, Y.; Kang, J. X.; Wu, Y. S.; Wu, Y. J. Adv. Synth. Catal. 2017, 359, 1976.
doi: 10.1002/adsc.v359.11
Min Yan , Zihao Ye , Ping Lu . Catalyst-free, visible-light-induced [2π + 2σ] cycloaddition towards azabicyclohexanes. Chinese Chemical Letters, 2025, 36(6): 110540-. doi: 10.1016/j.cclet.2024.110540
Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H4PMo11VO40 catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO2 catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
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
Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe2O4@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Kezhen Qi , Shu-yuan Liu , Ruchun Li . Selective dissolution for stabilizing solid electrolyte interphase. Chinese Chemical Letters, 2024, 35(5): 109460-. doi: 10.1016/j.cclet.2023.109460
Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
Rui PAN , Yuting MENG , Ruigang XIE , Daixiang CHEN , Jiefa SHEN , Shenghu YAN , Jianwu LIU , Yue ZHANG . Selective electrocatalytic reduction of Sn(Ⅳ) by carbon nitrogen materials prepared with different precursors. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1015-1024. doi: 10.11862/CJIC.20230433
Zhipeng Wan , Hao Xu , Peng Wu . Selective oxidation using in-situ generated hydrogen peroxide over titanosilicates. Chinese Journal of Structural Chemistry, 2024, 43(6): 100298-100298. doi: 10.1016/j.cjsc.2024.100298
Xuan Liu , Qing Li . Tailoring interatomic active sites for highly selective electrocatalytic biomass conversion reaction. Chinese Chemical Letters, 2025, 36(4): 110670-. doi: 10.1016/j.cclet.2024.110670
Shengtao Jiang , Mengjiao Xie , Limin Jin , Yifan Ren , Wentian Zheng , Siping Ji , Yanbiao Liu . New insights into electrocatalytic singlet oxygen generation for effective and selective water decontamination. Chinese Chemical Letters, 2025, 36(5): 110293-. doi: 10.1016/j.cclet.2024.110293
Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112