Citation: Yiyang Zhang, Wen Li, Zuofeng Hu, Xiaobi Jing, Lei Yu. Mo@PANI-catalyzed oxidative deoximation reaction[J]. Chinese Chemical Letters, ;2024, 35(2): 108938. doi: 10.1016/j.cclet.2023.108938 shu

Mo@PANI-catalyzed oxidative deoximation reaction

Yiyang Zhang ^{a, b, *,} ,
Wen Li ^b ,
Zuofeng Hu ^{b, c} ,
Xiaobi Jing ^b ,
Lei Yu ^{b, *,}

a.
School of Mechanical Engineering, Yangzhou University, Yangzhou 225127, China
b.
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
c.
Yangzhou Yangzi Auto Interior & Exterior Co., Ltd., Yangzhou 225119, China

008011@yzu.edu.cn

yulei@yzu.edu.cn

Received Date: 12 June 2023
Revised Date: 2 August 2023
Accepted Date: 17 August 2023
Available Online: 19 August 2023

Figures(4)

Deoximation is an important transformation in synthetic industry. It can be employed in protection, characterization and purification of the carbonyls, and in the synthesis of ketones from non-carbonyl molecules. In the field, oxidative deoximation reaction can utilize the driving force caused by the oxidation process so that the reaction can occur under relatively mild conditions. Recently, we designed and prepared polyaniline-supported molybdenum (Mo@PANI) just by immersing PANI into the EtOH/H₂O solution of MoCl₅. The material was successfully applied as the efficient catalyst for oxidative deoximation reactions, which were performed in ethanol using H₂O₂ as the clean oxidant. The substrate scope of the reaction was wide. It could be applied on heterocycle-containing substrates, making this protocol preferable for pharmaceutical intermediate synthesis. Since Mo is a necessary trace element for both animals and plants, this method is environment-friendly and is suitable for large-scale preparation. This work as the first example of Mo-catalyzed oxidative deoximation reaction may inspire novel ideas for both catalyst design and synthetic process development.
- Molybdenum,
- Polyaniline,
- Oxidation,
- Deoximation,
- Carbonyl
1. [1]
  G. Zhang, X. Wen, Y. Wang, W. Mo, C. Ding, Prog. Chem. 24 (2012) 361–369.
2. [2]
  Y. Zheng, A. Wu, Y. Ke, H. Cao, L. Yu, Chin. Chem. Lett. 30 (2019) 937–941. doi: 10.1016/j.cclet.2019.01.012
3. [3]
  E.J. Corey, P.B. Hopkins, S. Yoo, et al., J. Am. Chem. Soc. 101 (1979) 71311–77134.
4. [4]
  Q. Tong, Y. Liu, X. Gao, et al., Adv. Synth. Catal. 361 (2019) 3137–3145. doi: 10.1002/adsc.201900202
5. [5]
  E.E. Royals, S.E. Horne Jr, J. Am. Chem. Soc. 73 (1951) 5856–5857. doi: 10.1021/ja01156a119
6. [6]
  A. Grirrane, A. Corma, H. Garcia, J. Catal. 268 (2009) 350–355. doi: 10.1016/j.jcat.2009.10.005
7. [7]
  C. Isart, D. Bastida, J. Burés, J. Vilarrasa, Angew. Chem. Int. Ed. 50 (2011) 3275–3279. doi: 10.1002/anie.201007269
8. [8]
  P.K. Pradhan, S. Dey, P. Jaisankar, V.S. Giri, Synth. Commun. 35 (2005) 913–922. doi: 10.1081/SCC-200051681
9. [9]
  M.H. Lin, H.J. Liu, C.Y. Chang, W.C. Lin, T.H. Chuang, Molecules 17 (2012) 2464–2473. doi: 10.3390/molecules17032464
10. [10]
  L. Du, J. Gao, S. Yang, et al., Russ. J. Gen. Chem. 84 (2014) 2200–2204. doi: 10.1134/S1070363214110267
11. [11]
  Y. Liu, N. Yang, C. Chu, R. Liu, Chin. J. Chem. 33 (2015) 1011–1014. doi: 10.1002/cjoc.201500325
12. [12]
  C. Chen, Y. Yao, X. Wu, et al., Chin. Chem. Lett. 31 (2020) 1078–1082. doi: 10.1016/j.cclet.2019.12.019
13. [13]
  X. Xiao, Z. Shao, L. Yu, Chin. Chem. Lett. 32 (2021) 2933–2938. doi: 10.1016/j.cclet.2021.03.047
14. [14]
  J. Liu, Y. Cai, H. Pang, et al., Chin. Chem. Lett. 33 (2022) 4061–4063. doi: 10.1016/j.cclet.2021.12.068
15. [15]
  X. Jing, D. Yuan, L. Yu, Adv. Synth. Catal. 359 (2017) 1194–1201. doi: 10.1002/adsc.201601353
16. [16]
  C. Chen, X. Zhang, H. Cao, et al., Adv. Synth. Catal. 361 (2019) 603–610. doi: 10.1002/adsc.201801163
17. [17]
  X. Deng, H. Cao, C. Chen, H. Zhou, L. Yu, Sci. Bull. 64 (2019) 1280–1284. doi: 10.1016/j.scib.2019.07.007
18. [18]
  X. Deng, R. Qian, H. Zhou, L. Yu, Chin. Chem. Lett. 32 (2021) 1029–1032. doi: 10.1016/j.cclet.2020.09.012
19. [19]
  F. Wang, C. Yang, Y. Shi, L. Yu, Mol. Catal. 514 (2021) 111849. doi: 10.1016/j.mcat.2021.111849
20. [20]
  H. Li, X. Jing, Y. Shi, et al., React. Chem. Eng. 6 (2021) 119–124. doi: 10.1039/d0re00333f
21. [21]
  F. Wang, T. Chen, Y. Shi, L. Yu, Asian J. Org. Chem. 10 (2021) 614–618. doi: 10.1002/ajoc.202000675
22. [22]
  Z. Zeng, Y. Chen, X. Zhu, et al., Chin. Chem. Lett. 34 (2023) 107728. doi: 10.1016/j.cclet.2022.08.008
23. [23]
  H. Zhao, B. Zhu, J. Sekine, S.C. Luo, H.H. Yu, ACS Appl. Mater. Interfaces 4 (2012) 680–686. doi: 10.1021/am2012905
24. [24]
  Y. Liu, D. Tang, K. Cao, et al., J. Catal. 360 (2018) 250–260. doi: 10.1016/j.jcat.2018.01.026
25. [25]
  X. Meng, Y. Zhang, H. Hong, et al., ACS Sustain. Chem. Eng. 10 (2022) 7658–7663. doi: 10.1021/acssuschemeng.2c01540
26. [26]
  Y. Chen, L. Yu, H. Zhou, J. Phys. Chem. C 126 (2022) 17084–17092. doi: 10.1021/acs.jpcc.2c05290
27. [27]
  L. Yu, Y. Huang, Z. Wei, et al., J. Org. Chem. 80 (2015) 8677–8683. doi: 10.1021/acs.joc.5b01358
28. [28]
  A. Vijayakumar, Y. Zhao, J. Zou, et al., ChemSusChem 13 (2020) 5023–5030. doi: 10.1002/cssc.202001248
29. [29]
  M.J. García-Fernández, M.M. Pastor-Blas, F. Epron, Appl. Catal. B: Env. 225 (2018) 162–171. doi: 10.1016/j.apcatb.2017.11.064
30. [30]
  M. Sun, Z. Gong, J. Yi, et al., Chem. Commun. 56 (2020) 8798–8801. doi: 10.1039/d0cc03410j
31. [31]
  Y. Chen, X. Jing, L. Yu, Chin. J. Org. Chem. 40 (2020) 2570–2574. doi: 10.6023/cjoc202003044
32. [32]
  W. Li, F. Wang, Y. Shi, L. Yu, Chin. Chem. Lett. 34 (2023) 107505. doi: 10.1016/j.cclet.2022.05.019
33. [33]
  G. Gao, J. Han, L. Yu, Q. Xu, Synlett 30 (2019) 1703–1707. doi: 10.1055/s-0037-1612088
34. [34]
  Y. Chen, C. Chen, Y. Liu, L. Yu, Chin. Chem. Lett. 34 (2023) 108489. doi: 10.1016/j.cclet.2023.108489
35. [35]
  Y. Yuan, Z. Wang, Y. Su, J. Chem. Eng. Chin. Univ. 20 (2006) 548–553.
36. [36]
  K.R. Huber, R. Sridhar, E.H. Griffith, et al., Biochim. Biophys. Acta 915 (1987) 267–276. doi: 10.1016/0167-4838(87)90309-8
37. [37]
  G. Wood, C.J. Easton, A. Rauk, et al., J. Phys. Chem. A 110 (2006) 10316–10323. doi: 10.1021/jp062916j
38. [38]
  H. Mikami, S. Saito, S. Yamamoto, J. Chem. Phys. 94 (1991) 3415–3422. doi: 10.1063/1.459764
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