Citation: Zhang Qian, Yu Yanting, Li Jiale, Li Dong. The C5 C-H Bond Functionalization of Quinolines under Transition-Metal Free Conditions[J]. Chemistry, ;2020, 83(7): 615-620. shu

The C5 C-H Bond Functionalization of Quinolines under Transition-Metal Free Conditions

School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan, 430068

Corresponding author: Li Dong, dongli@mail.hbut.edu.cn
Received Date: 5 February 2020
Accepted Date: 9 March 2020

Quinoline is an important class of heterocyclic compounds, and research on the synthesis of quinoline compounds has attracted much attention. It is simple and efficient to prepare substituted quinolines though direct C-H bond functionalization of quinolines. However, the C5-selective C-H bond functionalization of quinolines is still a challenge. Most current methods are achieved by transition metal catalysis. The reactions under transition metal-free conditions are desired. In this paper, the recent advance of C5 C-H bond functionalization of quinolines under transition-metal free conditions is reviewed according to the types of bond (C-X, C-N, C-S, C-O and C-C) formation. And the research status and current problems in this field are also summarized.
- Quinoline,
- Transition-metal free,
- C-H bond functionalization,
- C5 of quinoline
1. [1]
  (a) Kaur K, Jain M, Reddy R P, et al. Eur. J. Med. Chem., 2010, 45(8): 3245~3264; (b) Colomb J, Becker G, Fieux S, et al. J. Med. Chem., 2014, 57(9): 3884~3890; (c) Hughes C C, MacMillan J B, Gaudêncio S P, et al. Angew. Chem. Int. Ed., 2009, 48(4): 725~727; (d) Pan E, Oswald N W, Legako A G, et al. Chem. Sci., 2013, 4(1): 482~488; (e) Pandey R R, Srivastava A, Malasoni R, et al. Bioorg. Med. Chem. Lett., 2012, 22(17): 5735~5738; (f) Vandekerckhove S, Müller C, Vogt D, et al. Bioorg. Med. Chem. Lett., 2013, 23(1): 318~322; (g) Vandekerckhove S, Tran H G, Desmet T, et al. Bioorg. Med. Chem. Lett., 2013, 23(16): 4641~4643; (h) Michael J P. Nat. Prod. Rep., 2008, 25(1): 166~187.
2. [2]
3. [3]
  (a) Berman A M, Lewis J C, Bergman R G, et al. J. Am. Chem. Soc., 2008, 130(45): 14926~14927; (b) Tobisu M, Hyodo I, Chatani N. J. Am. Chem. Soc., 2009, 131(34): 12070~12071; (c) Zhao D, Wang W, Yang F, et al. Angew. Chem. Int. Ed., 2009, 48(18): 3296~3300; (d) Ren X, Wen P, Shi X, et al. Org. Lett., 2013, 15(20): 5194~5197; (e) Sun K, Wang X, Liu L, et al. ACS Catal., 2015, 5(12): 7194~7198.
4. [4]
  (a) Ye M, Gao G L, Edmunds A J F, et al. J. Am. Chem. Soc., 2011, 133(47): 19090~19093; (b) Ye M, Gao G L, Yu J Q. J. Am. Chem. Soc., 2011, 133(18): 6964~6967; (c) Sun K, Lv Y, Wang J, et al. Org. Lett., 2015, 17(18) 4408~4411.
5. [5]
  (a) Tsai C, Shih W, Fang C, et al. J. Am. Chem. Soc., 2010, 132(34): 11887~11889; (b) Nakao Y, Yamada Y, Kashihara N, et al. J. Am. Chem. Soc., 2010, 132(39): 13666~13668; (c) Oshima K, Ohmura T, Suginome M. J. Am. Chem. Soc., 2011, 133(19): 7324~7327; (d) Hyodo I, Tobisu M, Chatani N. Chem. Asian J., 2012, 7(6): 1357~1365; (e) Chen Q, Jourdin X M D, Knochel P. J. Am. Chem. Soc., 2013, 135(13): 4958~4961; (f) Yamamoto S, Saga Y, Andou T, et al. Adv. Synth. Catal., 2014, 356(2~3): 401~405.
6. [6]
  (a) Kwak J, Kim M, Chang S. J. Am. Chem. Soc., 2011, 133(11) 3780~3787; (b) Konishi S, Kawamorita S, Iwai T, et al. Chem. Asian J., 2014, 9(2): 434~438.
7. [7]
  (a) Iwai T, Sawamura M. ACS Catal., 2015, 5(9): 5031~5040; (b) Khan B, Dutta H S, Koley D. Asian J. Org. Chem., 2018, 7, 1270~1297.
8. [8]
  Suess A M, Ertem M Z, Cramer C J, et al. J. Am. Chem. Soc., 2013, 135(26):9797~9804.
9. [9]
  Cong X, Zeng X. Org. Lett., 2014, 16(14):3716~3719.
10. [10]
  Zhu L, Qiu R, Cao X, et al. Org. Lett., 2015, 17(22):5528~5531.
11. [11]
  (a) Qiao H, Sun S, Yang F, et al. Org. Lett., 2015, 17(24): 6086~6089; (b) Liang H, Jiang K, Ding W, et al. Chem. Commun., 2015, 51(95): 16928~16931; (c) Wei J, Jiang J, Xiao X, et al. J. Org. Chem., 2016, 81(3): 946~955; (d) Zhu X, Zhang P, Ajitha M J, et al. Chem. Asian J., 2016, 11(6): 882~892.
12. [12]
  (a) Sun M M, Sun S Y, Qiao H J, et al. Org. Chem. Front., 2016, 3(12): 1646~1650; (b) Qiao H J, Sun S Y, Zhang Y, et al. Org. Chem. Front., 2017, 4(10): 1981~1986
13. [13]
  (a) Guo H, Chen M, Jiang P, et al. Tetrahedron 2015, 71(1): 70~76; (b) Xu J, Zhu X, Zhou G, et al. Org. Biomol. Chem., 2016, 14(11): 3016~3021; (c) Qiao H J, Sun S Y, Yang F, et al. Adv. Synth. Catal., 2017, 359(11): 1976~1980.
14. [14]
15. [15]
  Wang Y, Wang Y, Jiang K, et al. Org. Biomol. Chem., 2016, 14(43):10180~10184.
16. [16]
  Jiao J Y, Mao Y J, Feng A W, et al. Tetrahedron, 2017, 73(11):1482~1488.
17. [17]
  Chen X X, Wang J X, et al. Synlett, 2017, 28, 1840~1844.
18. [18]
  Qiao L, Cao X T, Chai K J, et al. Tetrahed. Lett., 2018, 59(23):2243~2247.
19. [19]
  Sen C, Sahoo T, Ghosh S C. Chemistry Select, 2017, 2(9):2745~2749.
20. [20]
21. [21]
  Chen J, Wang T, Liu Y, et al. Org. Chem. Front., 2017, 4(4):622~626.
22. [22]
  Li Y, Zhu L Z, Cao X, et al. Adv. Synth. Catal., 2017, 359(1):1~11.
23. [23]
  Dutta H S, Khan B, Raziullah A A K, et al. Chemistry Select, 2017, 2(22):6488~6492.
24. [24]
  Huang B B, Zhao Y T, Yang C, et al. Org. Lett., 2017, 19(14):3799~3802.
25. [25]
  Motati D R, Uredi D, Watkins E B. Chem. Sci., 2018, 9(7):1782~1788.
26. [26]
  Zhang Y C, Wen C X, Li J Z. Org. Biomol. Chem., 2018, 16(11):1912~1920.
27. [27]
  Chen H, Li P H, Wang M, et al. Eur. J. Org. Chem., 2018, (18):2091~2097.
28. [28]
  Wang Y, Wang Y, Guo Z Y, et al. Asian J. Org. Chem., 2016, 5(12):1438~1441.
29. [29]
  Ji D Z, He X, Xu Y Z, et al. Org. Lett., 2016, 18(18):4478~4481.
30. [30]
  Samanta S, Ravi C, Rao S N, et al. Org. Biomol. Chem., 2017, 15(45):9590~9594.
31. [31]
  Tang R J, Milcent T, Crousse B. Eur. J. Org. Chem., 2017, (32):4753~4757.
32. [32]
  Wang Y, Wang Y, Zhang Q, et al. Org. Chem. Front., 2017, 4(4):514~518.
33. [33]
  Shen C, Yang M, Xu J, et al. RSC Adv., 2017, 7(78):49436~49439.
34. [34]
  Begum Z, Bhavani G, Sridhar B. Synthesis, 2018, 50(20):4089~4096.
35. [35]
  Thrimurtulu N, Dey A, Pal K, et al. ChemistrySelect, 2017, 2(24):7251~7254.
36. [36]
  Mondal S, Hajra A, J. Org. Chem., 2018, 83(18):11392~11398.
37. [37]
  Yao X H, Weng X, Wang K X, et al. Green Chem., 2018, 20(11):2472~2476.
38. [38]
  Wu Z Y, He Y Q, Ma C W, et al. Asian J. Org. Chem., 2016, 5(6):724~728.
39. [39]
  Xu J, Qiao L, Ying B, et al. Org. Chem. Front., 2017, 4(6):1116~1120.
40. [40]
  Arockiam P B, Guillemard L, Wencel-Delord J. Adv. Synth. Catal., 2017, 359(15):2571~2579.
41. [41]
  Zhao L, Li P, Xie X, et al. Org. Chem. Front., 2018, 5(10):1689~1697.
1. [1]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
2. [2]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
3. [3]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
4. [4]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
5. [5]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
6. [6]
  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
7. [7]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
8. [8]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
9. [9]
  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
10. [10]
  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
11. [11]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
12. [12]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
13. [13]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
14. [14]
  Wen Jiang , Jieli Lin , Zhongshu Li . 低配位含磷官能团的研究进展. University Chemistry, 2025, 40(8): 138-151. doi: 10.12461/PKU.DXHX202409144
15. [15]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
16. [16]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
17. [17]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d-Band Center Regulated O₂ Adsorption on Transition Metal Single Atoms Loaded COF: A DFT Study. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-0. doi: 10.3866/PKU.WHXB202407013
18. [18]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-0. doi: 10.3866/PKU.WHXB202407005
19. [19]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
20. [20]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1171)
HTML views(298)

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