Citation: Zhiwei Wang, Qishun Liu, Ruisheng Liu, Zhongyin Ji, Yan Li, Xiaohui Zhao, Wei Wei. Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones[J]. Chinese Chemical Letters, ;2022, 33(3): 1479-1482. doi: 10.1016/j.cclet.2021.08.036 shu

Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones

Zhiwei Wang ^a ,
Qishun Liu ^a ,
Ruisheng Liu ^a ,
Zhongyin Ji ^a ,
Yan Li ^a ,
Xiaohui Zhao ^b ,
Wei Wei ^{a, *,}

a.
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China
b.
Qinghai Provincial Key Laboratory of Tibetan Medicine Research and Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Qinghai 810008, China

weiweiqfnu@163.com

Received Date: 9 June 2021
Revised Date: 6 August 2021
Accepted Date: 8 August 2021
Available Online: 12 August 2021

Figures(7)

A mild and efficient photochemical multi-component tandem reaction of quinoxalin-2(1H)-ones, alkenes and sulfinic acids is reported. This tandem reaction could be conveniently carried out at room temperature by employing 4CzIPN as the metal-free photocatalyst and dioxygen (air) as the environmentally benign oxidant. A number of sulfonated quinoxalin-2(1H)-ones were obtained in satisfactory yields with favorable functional group tolerance. Radical trapping experiment and fluorescence quenching experiments were performed to elucidate this visible-light mediated radical reaction process.
- Visible-light,
- Multi-component reaction,
- Radical process,
- Sulfonated quinoxalin-2(1H)-ones
1. [1]
  N. Udilova, A.V. Kozlov, W. Bieberschulte, et al., Biochem. Pharmacol. 65(2003) 59-65. doi: 10.1016/S0006-2952(02)01452-1
2. [2]
  H. Nohl, W. Bieberschulte, B. Dietrich, N. Udilova, A.V. Kozlov, J. Heterocycl. Chem. 43(2006) 541-548. doi: 10.1002/jhet.5570430304
3. [3]
  Q. Ke, G. Yan, J. Yu, X. Wu, Org. Biomol. Chem. 17(2019) 5863-5881. doi: 10.1039/C9OB00782B
4. [4]
  J. Yuan, S. Liu, Y. Xiao, et al., Org. Biomol. Chem. 17(2019) 876-884. doi: 10.1039/C8OB03061H
5. [5]
  Y. Li, M. Gao, L. Wang, X. Cui, Org. Biomol. Chem. 14(2016) 8428-8432. doi: 10.1039/C6OB01283C
6. [6]
  W. Wei, L. Wang, P. Bao, et al., Org. Lett. 20(2018) 7125-7130. doi: 10.1021/acs.orglett.8b03079
7. [7]
  J.W. Yuan, J.H. Fu, S.N. Liu, et al., Org. Biomol. Chem. 16(2018) 3203-3212. doi: 10.1039/C8OB00206A
8. [8]
  L.Y. Xie, S. Peng, T.G. Fan, et al., Sci. China Chem. 62(2019) 460-464. doi: 10.1007/s11426-018-9446-1
9. [9]
  P. Bao, F. Liu, Y. Lv, et al., Org. Chem. Front. 7(2020) 492-498. doi: 10.1039/C9QO01334B
10. [10]
  L.Y. Xie, Y.S. Bai, X.Q. Xu, et al., Green Chem. 22(2020) 1720-1725. doi: 10.1039/C9GC03899J
11. [11]
  J. Yuan, J. Fu, J. Yin, et al., Org. Chem. Front. 5(2018) 2820-2828. doi: 10.1039/C8QO00731D
12. [12]
  W. Wei, L. Wang, H. Yue, et al., ACS Sustain. Chem. Eng. 6(2018) 17252-17257. doi: 10.1021/acssuschemeng.8b04652
13. [13]
  L.Y. Xie, L.L. Jiang, J.X. Tan, et al., ACS Sustain. Chem. Eng. 7(2019) 14153-14160. doi: 10.1021/acssuschemeng.9b02822
14. [14]
  S. Paul, J.H. Ha, G.E. Park, Y.R. Lee, Adv. Synth. Catal. 359(2017) 1515-1521. doi: 10.1002/adsc.201700070
15. [15]
  J. Yuan, S. Liu, L. Qu, Adv. Synth. Catal. 359(2017) 4197-4207. doi: 10.1002/adsc.201701058
16. [16]
  L. Wang, P. Bao, W. Liu, et al., Chin. J. Org. Chem. 38(2018) 3189-3196. doi: 10.6023/cjoc201807014
17. [17]
  M. Gao, Y. Li, L. Xie, R. Chauvin, X. Cui, Chem. Commun. 52(2016) 2846-2849. doi: 10.1039/C5CC08049E
18. [18]
  K.J. Li, Y.Y. Jiang, K. Xu, C.C. Zeng, B.G. Sun, Green Chem. 21(2019) 4412-4421. doi: 10.1039/C9GC01474H
19. [19]
  J. Wang, B. Sun, L. Zhang, et al., Org. Chem. Front. 7(2020) 113-118. doi: 10.1039/C9QO01055F
20. [20]
  L. Yang, P. Gao, X.H. Duan, Y.R. Gu, L.N. Guo, Org. Lett. 20(2018) 1034-1037. doi: 10.1021/acs.orglett.7b03984
21. [21]
  L.Y. Xie, Y.L. Chen, L. Qin, et al., Org. Chem. Front. 6(2019) 3950-3955. doi: 10.1039/C9QO01240K
22. [22]
  J. Zhou, P. Zhou, T. Zhao, Q. Ren, J. Li, Adv. Synth. Catal. 361(2019) 5371-5382. doi: 10.1002/adsc.201901008
23. [23]
  J. Xu, H. Yang, H. Cai, et al., Org. Lett. 21(2019) 4698-4702. doi: 10.1021/acs.orglett.9b01578
24. [24]
  L.Y. Xie, Y.S. Liu, H.R. Ding, et al., Chin. J. Catal. 41(2020) 1168-1173. doi: 10.1016/S1872-2067(19)63526-6
25. [25]
  Q.W. Gui, F. Teng, S.N. Ying, et al., Chin. Chem. Lett. 31(2020) 3241-3244. doi: 10.1016/j.cclet.2020.07.017
26. [26]
  L.H. Lu, Z. Wang, W. Xia, et al., Chin. Chem. Lett. 30(2019) 1237-1240. doi: 10.1016/j.cclet.2019.04.033
27. [27]
  Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31(2019) 373-376.
28. [28]
  Z. Gan, G. Li, Q. Yan, et al., Green Chem. 22(2020) 2956-2962. doi: 10.1039/D0GC00070A
29. [29]
  D. Hu, L. Yang, J.P. Wan, Green Chem. 22(2020) 6773-6777. doi: 10.1039/D0GC02806A
30. [30]
  L. Yang, J.P. Wan, Green Chem. 22(2020) 3074-3078. doi: 10.1039/D0GC00738B
31. [31]
  Q.W. Gui, X. He, W. Wang, et al., Green Chem. 22(2020) 118-122. doi: 10.1039/C9GC02657F
32. [32]
  Y. Wu, J.Y. Chen, J. Ning, et al., Green Chem. 23(2021) 3950-3954. doi: 10.1039/D1GC00562F
33. [33]
  J. Shen, J. Xu, L. Huang, Q. Zhu, P. Zhang, Adv. Synth. Catal. 362(2020) 230-241. doi: 10.1002/adsc.201901314
34. [34]
  C.D. Clinton, C.D. Prasad, R.S. Thombal, Y.R. Lee, Adv. Synth. Catal. 363(2021) 776-784. doi: 10.1002/adsc.202001182
35. [35]
  Z. Shao, S. Zhang, Y. Chen, et al., Tetrahedron 76(2020) 131199. doi: 10.1016/j.tet.2020.131199
36. [36]
  N. Meng, L. Wang, Q. Liu, et al., J. Org. Chem. 85(2020) 6888-6896. doi: 10.1021/acs.joc.9b03505
37. [37]
  H.S. Dutta, A. Ahmad, A.A. Khan, et al., Adv. Synth. Catal. 361(2019) 5534-5539. doi: 10.1002/adsc.201901212
38. [38]
  J.R. Chen, X.Q. Hu, L.Q. Lu, W.J. Xiao, Chem. Soc. Rev. 45(2016) 2044-2056. doi: 10.1039/C5CS00655D
39. [39]
  Z.J. Shen, H.N. Shi, W.J. Hao, S.J. Tu, B. Jiang, Chem. Commun. 54(2018) 11542-11545. doi: 10.1039/C8CC06086J
40. [40]
  Y. Chen, L.Q. Lu, D.G. Yu, C.J. Zhu, W.J. Xiao, Sci. China Chem. 63(2020) 1652-1658. doi: 10.1007/s11426-020-9811-6
41. [41]
  P. Bao, F. Liu, Y. Lv, et al., Org. Chem. Front. 7(2020) 492-498. doi: 10.1039/C9QO01334B
42. [42]
  W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31(2020) 1895-1898. doi: 10.1016/j.cclet.2020.02.011
43. [43]
  S. He, X. Chen, F. Zeng, et al., Chin. Chem. Lett. 31(2020) 1863-1867. doi: 10.1016/j.cclet.2019.12.031
44. [44]
  Z. Gan, G. Li, X. Yang, et al., Sci. China. Chem. 63(2020) 1652-1658. doi: 10.1007/s11426-020-9811-6
45. [45]
  L.Y. Xie, T.G. Fang, J.X. Tan, et al., Green Chem. 21(2019) 3858-3863. doi: 10.1039/C9GC01175G
46. [46]
  D.Q. Dong, L.X. Li, G.H. Li, et al., Chin. J. Catal. 40(2019) 1494-1498. doi: 10.1016/S1872-2067(19)63420-0
47. [47]
  Q. Liu, L. Wang, H. Yue, et al., Green Chem. 21(2019) 1609-1613. doi: 10.1039/C9GC00222G
48. [48]
  M.H. Huang, C.F. Zhu, C.L. He, et al., Org. Chem. Front. 5(2018) 1643-1650. doi: 10.1039/C8QO00098K
49. [49]
  Q.Q. Ge, J.S. Qian, J. Xuan, J. Org. Chem. 84(2019) 8691-8701. doi: 10.1021/acs.joc.9b00552
50. [50]
  D. Chen, Y. Sun, D. Dong, Q. Han, Z. Wang, Chin. J. Org. Chem. 40(2020) 4267-4273. doi: 10.6023/cjoc202006025
51. [51]
  S. Peng, Y. Lin, W. He, Chin. J. Org. Chem. 40(2020) 541-542. doi: 10.6023/cjoc202000006
52. [52]
  X.Y. Yu, J.R. Chen, W.J. Xiao, Chem. Rev. 121(2021) 506-561. doi: 10.1021/acs.chemrev.0c00030
53. [53]
  X. Gong, X. Li, W. Xie, J. Wu, S. Ye, Org. Chem. Front. 6(2019) 1863-1867. doi: 10.1039/C9QO00410F
54. [54]
  S. Garbarino, D. Ravelli, S. Protti, A. Basso, Angew. Chem. Int. Ed. 55(2016) 15476-15484. doi: 10.1002/anie.201605288
55. [55]
  X. Gong, M. Yang, J.B. Liu, et al., Green Chem. 22(2020) 1906-1910. doi: 10.1039/D0GC00332H
56. [56]
  Y. Li, T. Miao, P. Li, L. Wang, Org. Lett. 20(2018) 1735-1739. doi: 10.1021/acs.orglett.8b00171
57. [57]
  Y. Lv, P. Bao, H. Yue, J.S. Li, W. Wei, Green Chem. 21(2019) 6051-6055. doi: 10.1039/C9GC03253C
58. [58]
  D. Zheng, A. Studer, Org. Lett. 21(2019) 325-329. doi: 10.1021/acs.orglett.8b03849
59. [59]
  N. Meng, Y. Lv, Q. Liu, et al., Chin. Chem. Lett. 32(2021) 258-262. doi: 10.1016/j.cclet.2020.11.034
60. [60]
  M.D. McReynolds, J.M. Dougherty, P.R. Hanson, Chem. Rev. 104(2004) 2239-2258. doi: 10.1021/cr020109k
61. [61]
  Q.A. Acton, Sulfones-Advances in Research and Application, Scholarly Editions, Atlanta, 2013.
62. [62]
  Q. Yu, Y. Liu, J.P. Wan, Chin. Chem. Lett. 32(2021) 3514-3517. doi: 10.1016/j.cclet.2021.04.037
63. [63]
  L. Wang, M. Zhang, Y. Zhang, et al., Chin. Chem. Lett. 31(2020) 67-70. doi: 10.1016/j.cclet.2019.05.041
64. [64]
  W. Wei, C. Liu, D. Yang, et al., Chem. Commun. 49(2013) 10239-10241. doi: 10.1039/c3cc45803b
65. [65]
  Q. Liu, F. Liu, H. Yue, et al., Adv. Synth. Catal. 361(2019) 5277-5282. doi: 10.1002/adsc.201900984
66. [66]
  Q. Liu, Y. Lv, R. Liu, et al., Chin. Chem. Lett. 32(2021) 136-139. doi: 10.1016/j.cclet.2020.11.059
67. [67]
  T.Y. Shang, L.H. Lu, Z. Cao, et al., Chem. Commun. 55(2019) 5408-5419. doi: 10.1039/C9CC01047E
68. [68]
  S. He, X. Chen, F. Zeng, et al., Chin. Chem. Lett. 31(2020) 1863-1867. doi: 10.1016/j.cclet.2019.12.031
69. [69]
  A.K. Ghosh, S. Mondal, A. Hajra, Org. Lett. 22(2020) 2771-2775. doi: 10.1021/acs.orglett.0c00759
70. [70]
  Q. Lu, J. Zhang, F. Wei, et al., Angew. Chem. Int. Ed. 52(2013) 7156-7159. doi: 10.1002/anie.201301634
71. [71]
  W. Wei, J. Wen, D. Yang, et al., Org. Biomol. Chem. 12(2014) 7678-7681. doi: 10.1039/C4OB01369G
72. [72]
  Z. Peng, Y.Y. Hong, S. Peng, et al., Org. Biomol. Chem. 19(2021) 4537-4541. doi: 10.1039/D1OB00552A
1. [1]
  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
2. [2]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
3. [3]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
4. [4]
  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
5. [5]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
6. [6]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
7. [7]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
8. [8]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
9. [9]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
10. [10]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
11. [11]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329
12. [12]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
13. [13]
  Xin Wang , Changzhao Chen , Qishen Wang , Kai Dai . Graphene quantum dot modified Bi2MoO6 nanoflower for efficient degradation of BPA under visible light. Chinese Journal of Structural Chemistry, 2024, 43(12): 100473-100473. doi: 10.1016/j.cjsc.2024.100473
14. [14]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
15. [15]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
16. [16]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
17. [17]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
18. [18]
  Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP₂/C anode with native oxidation PO_x component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
19. [19]
  Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
20. [20]
  Zhao-Bo Hu , Ling-Ao Gui , Long-He Li , Tong-Tong Xiao , Adam T. Hand , Pagnareach Tin , Mykhaylo Ozerov , Yan Peng , Zhongwen Ouyang , Zhenxing Wang , Zi-Ling Xue , You Song . Co^Ⅱ single-ion magnet and its multi-dimensional aggregations: Influence of the structural rigidity on magnetic relaxation process. Chinese Chemical Letters, 2025, 36(2): 109600-. doi: 10.1016/j.cclet.2024.109600

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(709)
HTML views(137)

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