Citation: Yufen Lv, Hongyu Ding, Jinmao You, Wei Wei, Dong Yi. Additive-free synthesis of S-substituted isothioureas via visible-light-induced four-component reaction of α-diazoesters, aryl isothiocyanates, amines and cyclic ethers[J]. Chinese Chemical Letters, ;2024, 35(2): 109107. doi: 10.1016/j.cclet.2023.109107 shu

Additive-free synthesis of S-substituted isothioureas via visible-light-induced four-component reaction of α-diazoesters, aryl isothiocyanates, amines and cyclic ethers

Yufen Lv ^{a, 1} ,
Hongyu Ding ^{a, 1} ,
Jinmao You ^{a, b, *,} ,
Wei Wei ^{a, *,} ,
Dong Yi ^{c, **,}

a.
Key Laboratory of Catalytic Conversion and Clean Energy in Universities of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China
b.
College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, China
c.
School of Pharmacy, Southwest Medical University, Luzhou 646000, China

^**

jmyou6304@163.com

weiweiqfnu@163.com

yidong@swmu.edu.cn

Received Date: 25 July 2023
Revised Date: 8 September 2023
Accepted Date: 14 September 2023
Available Online: 16 September 2023

Figures(8)

An additive-free and environmentally friendly strategy has been realized for the construction of S-substituted isothioureas through visible-light-induced multicomponent reaction starting from α-diazoesters, aryl isothiocyanates, amines and cyclic ethers. This methodology features simple operation, mild reaction conditions, favorable functional group tolerance, easily available starting materials and high efficiency.
- Visible-light,
- Additive-free,
- Four-component reaction,
- S-Substituted isothioureas
1. [1]
  T. Castanheiro, J. Suffert, M. Donnard, M. Gulea, Chem. Soc. Rev. 45 (2016) 494–505. doi: 10.1039/C5CS00532A
2. [2]
  A. Kamble, R. Kamble, S. Dodamani, et al., Arch. Pharmacal. Res. 40 (2017) 444–4573. doi: 10.1007/s12272-017-0887-0
3. [3]
  H. Xu, X. Li, J. Ma, et al., Chin. Chem. Lett. 34 (2023) 108403. doi: 10.1016/j.cclet.2023.108403
4. [4]
  Y. Lv, H. Cui, N. Meng, et al., Chin. Chem. Lett. 33 (2022) 97–114. doi: 10.1117/12.2642676
5. [5]
  X. Wang, Z. Wang, Z. Li, K. Sun, Chin. Chem. Lett. 34 (2023) 108045. doi: 10.1016/j.cclet.2022.108045
6. [6]
  J. Jiang, Z. Wang, W.M. He, Chin. Chem. Lett. 32 (2021) 1591–1592. doi: 10.1016/j.cclet.2021.02.067
7. [7]
  X. Wang, J. Meng, D. Zhao, et al., Chin. Chem. Lett. 34 (2023) 107736. doi: 10.1016/j.cclet.2022.08.016
8. [8]
  Y. Qi, X. Gu, X. Huang, et al., Chin. Chem. Lett. 32 (2021) 3544–3547. doi: 10.1016/j.cclet.2021.05.069
9. [9]
  A. Mertens, B. Koenig, U. Leser, Patent: DE4325741, 1995.
10. [10]
  Q. Chen, X.L. Zhu, L.L. Jiang, et al., Eur. J. Med. Chem. 43 (2008) 595–603. doi: 10.1016/j.ejmech.2007.04.021
11. [11]
  D. Kommula, P. K. Chintakunta, K. Garikapati, M.S.R. Murty, Mol. Divers. 27 (2023) 425–441. doi: 10.1007/s11030-022-10432-6
12. [12]
  A. Pascual, A. Rindlisbacher, Pest. Manage. Sci. 42 (1994) 253–263. doi: 10.1002/ps.2780420402
13. [13]
  G.L. Perlovich, A.N. Proshin, T.V. Volkova, et al., J. Med. Chem. 52 (2009) 1845–1852. doi: 10.1021/jm8012882
14. [14]
  P. Polucci, P. Magnaghi, M. Angiolini, J. Med. Chem. 56 (2013) 437–450. doi: 10.1021/jm3013213
15. [15]
  V.N. Danilenko, A.Y. Simonov, S.A. Lakatosh, J. Med. Chem. 51 (2008) 7731–7736. doi: 10.1021/jm800758s
16. [16]
  C. Mugnaini, F. Manetti, J. A. Este, et al., Bioorg. Med. Chem. Lett. 16 (2006) 3541–3544. doi: 10.1016/j.bmcl.2006.03.080
17. [17]
  A.R. Katritzky, B.V. Rogovoy, ARKIVOC. 4 (2005) 49–87. doi: 10.3998/ark.5550190.0006.406
18. [18]
  T.R.M. Rauws, B.U.W. Maes, Chem. Soc. Rev. 41 (2012) 2463–2497. doi: 10.1039/c1cs15236j
19. [19]
  C. Alonso-Moreno, A. Antiñolo, F. Carillo-Hermosilla, Chem. Soc. Rev. 43 (2014) 3406–3425. doi: 10.1039/C4CS00013G
20. [20]
  G. Khalili, Monatsh Chem. 146 (2015) 1891–1894. doi: 10.1007/s00706-015-1465-0
21. [21]
  A.R. Katritzky, B. Rogovoy, C. Klein, et al., J. Org. Chem. 66 (2001) 2854–2857. doi: 10.1021/jo001685o
22. [22]
  C. Levallet, J. Lerpiniere, S.Y. Ko, Tetrahedron 53 (1997) 5291–5304. doi: 10.1016/S0040-4020(97)00193-2
23. [23]
  S.K. Hamilton, D.E. Wilkinson, G.S. Hamilton, Y.Q. Wu, Org. Lett. 7 (2005) 2429–2431. doi: 10.1021/ol050728q
24. [24]
  H. Sandin, M.L. Swanstein, E. Wellner, J. Org. Chem. 69 (2004) 1571–1580. doi: 10.1021/jo030338m
25. [25]
  X. Liu, H. Zhu, S.B. Zhang, et al., Tetrahedron Lett. 59 (2018) 3165–3170. doi: 10.1016/j.tetlet.2018.07.012
26. [26]
  H. Zhu, X. Liu, C. Chang, Z. Dong, Synthesis 49 (2017) 5211–5216. doi: 10.1055/s-0036-1590879
27. [27]
  G. He, Y. Huang, Y. Tong, et al., Tetrahedron Lett 54 (2013) 5318–5321. doi: 10.1016/j.tetlet.2013.07.096
28. [28]
  Y.X. Wu, X. Wang, J.H. Li, et al., Eur. J. Org. Chem. (2022) e202200707.
29. [29]
  X.H. Xu, E.J. Hao, Z. Shi, Z.B. Dong, J. Org. Chem. 87 (2022) 9675–9687. doi: 10.1021/acs.joc.2c00728
30. [30]
  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
31. [31]
  Q. Huang, L. Zhu, D. Yi, et al. Chin. Chem. Lett. 31 (2020) 373–376. doi: 10.1016/j.cclet.2019.07.049
32. [32]
  N. Meng, Q. Liu, R. Liu, et al., Chin. J. Org. Chem. 41 (2022) 4639–4650.
33. [33]
  D. Hu, L. Yang, J. P. Wan, Green Chem. 22 (2020) 6773–6777. doi: 10.1039/d0gc02806a
34. [34]
  P. Mampuys, Y. Zhu, T. Vlaar, et al., Angew. Chem. Int. Ed. 53 (2014) 12849–12854. doi: 10.1002/anie.201406717
35. [35]
  D. Mishra, P. Phukan, J. Org. Chem. 86 (2021) 17581–17593. doi: 10.1021/acs.joc.1c01578
36. [36]
  S. Liu, L. Jiang, Org. Lett. 24 (2022) 7157–7162. doi: 10.1021/acs.orglett.2c02854
37. [37]
  W.B. He, S.J. Zhao, J.Y. Chen, et al., Chin. Chem. Lett. 34 (2023) 107640. doi: 10.1016/j.cclet.2022.06.063
38. [38]
  N. Meng, Y. Lv, Q. Liu, et al., Chin. Chem. Lett. 32 (2021) 258–262. doi: 10.1016/j.cclet.2020.11.034
39. [39]
  J. Xuan, X. K. He, W. J. Xiao, Chem. Soc. Rev. 49 (2020) 2546–2556. doi: 10.1039/c9cs00523d
40. [40]
  D. Yang, Q. Yan, E. Zhu, et al., Chin. Chem. Lett. 33 (2022) 1798–1816. doi: 10.1016/j.cclet.2021.09.068
41. [41]
  X.Y. Yu, J.R. Chen, W.J. Xiao, Chem. Rev. 121 (2021) 506–561. doi: 10.1021/acs.chemrev.0c00030
42. [42]
  T. Zou, Y. He, R. Liu, et al., Chin. Chem. Lett. 34 (2023) 107822. doi: 10.1016/j.cclet.2022.107822
43. [43]
  Z. Wang, N. Meng, Y. Lv, et al., Chin. Chem. Lett. 34 (2023) 107599. doi: 10.1016/j.cclet.2022.06.022
44. [44]
  H. Xu, J. Zhang, J. Zuo, et al., Chin. J. Org. Chem. 42 (2022) 4037–4059. doi: 10.6023/cjoc202209004
45. [45]
  S. Zhou, B. Cai, C. Hu, et al., Chin. Chem. Lett. 32 (2021) 2577–2581. doi: 10.1016/j.cclet.2021.03.010
46. [46]
  C. Qu, R. Liu, Z. Wang, et al., Green Chem. 24 (2022) 4915–4920. doi: 10.1039/d2gc00903j
47. [47]
  Z. Wang, Q. Liu, R. Liu, et al., Chin. Chem. Lett. 33 (2022) 1479–1482. doi: 10.1016/j.cclet.2021.08.036
48. [48]
  Q. Liu, Y. Lv, R. Liu, et al., Chin. Chem. Lett. 32 (2021) 136–139. doi: 10.1016/j.cclet.2020.11.059
49. [49]
  Q. Liu, L. Wang, H. Yue, et al., Green Chem. 21 (2019) 1609–1613. doi: 10.1039/c9gc00222g
50. [50]
  D. Yi, L. He, Z. Qi, et al., Chin. J. Chem. 39 (2021) 859–865. doi: 10.1002/cjoc.202000549
51. [51]
  Z. Yang, M.L. Stivanin, I.D. Jurberg, R.M. Koenigs, Chem. Soc. Rev. 49 (2020) 6833–6847. doi: 10.1039/d0cs00224k
52. [52]
  H. Ding, Z. Wang, C. Qu, et al., Org. Chem. Front. 9 (2022) 5530–5535. doi: 10.1039/d2qo01082h
53. [53]
  B.G. Cai, J. Xuan, Chin. J. Org. Chem. 41 (2021) 4565–4574. doi: 10.6023/cjoc202109040
54. [54]
  L. Qian, B.G. Cai, L. Li, J. Xuan, Org. Lett. 23 (2021) 6951–6955. doi: 10.1021/acs.orglett.1c02555
55. [55]
  B.G. Cai, Q. Li, Q. Zhang, et al., Org. Chem. Front. 8 (2021) 5982–5987. doi: 10.1039/d1qo01102b
56. [56]
  R. Liu, S. Fu, X. Chu, et al., Chin. J. Org. Chem. 42 (2022) 2462–2470. doi: 10.6023/cjoc202204014
57. [57]
  Y.N. Wang, X. Wang, S.J. Li, Y. Lan, Org. Chem. Front. 9 (2022) 1247–1253. doi: 10.1039/d1qo01730f
1. [1]
  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
2. [2]
  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
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]
  Jindong Hao , Yufen Lv , Shuyue Tian , Chao Ma , Wenxiu Cui , Huilan Yue , Wei Wei , Dong Yi . Additive-free synthesis of β-keto phosphorodithioates via geminal hydro-phosphorodithiolation of sulfoxonium ylides with P₄S₁₀ and alcohols. Chinese Chemical Letters, 2024, 35(9): 109513-. doi: 10.1016/j.cclet.2024.109513
5. [5]
  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
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]
  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
8. [8]
  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
9. [9]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
10. [10]
  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
11. [11]
  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
12. [12]
  Kunyao Peng , Xianbin Wang , Xingbin Yan . Converting LiNO₃ additive to single nitrogenous component Li₂N₂O₂ SEI layer on Li metal anode in carbonate-based electrolyte. Chinese Chemical Letters, 2024, 35(9): 109274-. doi: 10.1016/j.cclet.2023.109274
13. [13]
  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
14. [14]
  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
15. [15]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
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]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
18. [18]
  Yuting Wu , Haifeng Lv , Xiaojun Wu . Design of two-dimensional porous covalent organic framework semiconductors for visible-light-driven overall water splitting: A theoretical perspective. Chinese Journal of Structural Chemistry, 2024, 43(11): 100375-100375. doi: 10.1016/j.cjsc.2024.100375
19. [19]
  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
20. [20]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(291)
HTML views(12)

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