Citation: Cong Yikang, Zeng Xianghua. Nano Cu-CuFe₂O₄-Catalyzed Selective Reduction of α, β, γ, δ-Unsaturated Carbonyls in Alcohol Medium[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2411-2418. doi: 10.6023/cjoc202003049 shu

Nano Cu-CuFe₂O₄-Catalyzed Selective Reduction of α, β, γ, δ-Unsaturated Carbonyls in Alcohol Medium

Cong Yikang ,
Zeng Xianghua ^,

College of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001

Corresponding author: Zeng Xianghua, xianghuazeng@zjxu.edu.cn
Received Date: 20 March 2020
Revised Date: 11 May 2020
Available Online: 27 May 2020
Fund Project: National Natural Science Foundation of Zhejiang Province LY17B030011Project supported by the National Natural Science Foundation of Zhejiang Province (No. LY17B030011)

Figures(6)

An efficient Cu-CuFe₂O₄ nanoparticle-catalyzed protodeboronation strategy has been developed for the chemoselective 1, 4-reduction of α, β, γ, δ-unsaturated ketones, carboxylic ester and cyano-ester. This protocol has the advantageous of the use of alcohol as hydrogen source and solvent, low catalyst loading (0.5 mol%), and excellent catalyst recyclability. Additionally, the Cu-CuFe₂O₄ catalyst has shown excellent performance in gram-scale reactions. Furthermore, the catalytic mechanism has also been discussed. The reactivity of (E)-γ, δ-unsaturated carbonyl products, an important class of γ, δ-unsaturated alkenes, enables easy access to 3-buten-1-ols, 3-buten-1-amines, γ-keto acids, cyclic ethers, and cyclic nitrones.
- α, β, γ, δ-unsaturated carbonyls,
- nano Cu-CuFe₂O₄,
- chemoselective,
- 1, 4-reduction
1. [1]
  (a) Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley & Sons, Hoboken, NJ, 2007.
  (b) Andersson, P. G.; Munslow, I. J. Modern Reduction Methods, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008.
2. [2]
  For selected examples, see: (a) Wang, X.; Han, Z.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 936.
  (b) Sasson, Y.; Blum, J. J. Org. Chem. 1975, 40, 1887.
  (c) Li, W.; Wu, X-F. Eur. J. Org. Chem. 2015, 331.
  (d) Ding, B.; Zhang, Z.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Org. Lett. 2013, 15, 3690.
  (e) Zhang, B.-H.; Shi, L.-X.; Guo, R.-X. Helv. Chim. Acta 2013, 96, 2152.
  (f) Zhou, X.; Li, X.; Zhang, W.; Chen, J. Tetrahedron Lett. 2014, 55, 5137.
3. [3]
  Nussim, M.; Mazur, Y.; Sondheimer, F. J. Org. Chem. 1964, 29, 1120. doi: 10.1021/jo01028a032
4. [4]
  Ranu, B. C.; Samanta, S. J. Org. Chem. 2003, 68, 7130. doi: 10.1021/jo0347821
5. [5]
  Huang, X.; Hu, J.; Wu, M.; Wang, J.; Peng, Y.; Song, G. Green Chem. 2018, 20, 255. doi: 10.1039/C7GC02863F
6. [6]
  Zhou, Y.; Rao, C.; Song, Q. Org. Lett., 2016, 18, 4000. doi: 10.1021/acs.orglett.6b01816
7. [7]
  (a) An, K.; Somorjai, G. A. Catal. Lett. 2015, 145, 233.
  (b) Singh, A. K.; Xu, Q. ChemCatChem 2013, 5, 652.
  (c) Sankar, M.; Dimitratos, N.; Miedziak, P. J.; Wells, P. P.; Kiely, C. J.; Hutchings, G. J. Chem. Soc. Rev. 2012, 41, 8099.
8. [8]
  Valden, M.; Lai, X.; Goodman, D. W. Science 1998, 281, 1647. doi: 10.1126/science.281.5383.1647
9. [9]
  Jin, C.; Wang, Y.; Wei, H.; Tang, H.; Liu, X.; Lu, T.; Wang, J. J. Mater. Chem. A 2014, 2, 11202. doi: 10.1039/c4ta00258j
10. [10]
  Yang, W.; Wei, L.; Yi, F.; Cai, M. Catal. Sci. Technol. 2016, 6, 4554. doi: 10.1039/C5CY02159F
11. [11]
  Wang, D.; Etienne, L.; Echeverria, M.; Moya, S.; Astruc, D. Chem.-Eur. J. 2014, 20, 4047. doi: 10.1002/chem.201304536
12. [12]
  Jang, J.; Byun, S.; Kim, B. M.; Lee, S. Chem. Commun. 2018, 54, 3492. doi: 10.1039/C7CC09926F
13. [13]
  Zhang, L.; Li, P.; Liu, C.; Yang, J.; Wang M.; Zhang, L. Catal. Sci. Technol. 2014, 4, 1979. doi: 10.1039/C4CY00040D
14. [14]
  Polshettiwar, V.; Varma, R. S. Chem.-Eur. J. 2009, 15, 1582. doi: 10.1002/chem.200802264
15. [15]
  Abu-Reziq, R.; Alper, H.; Wang, D.; Post, M. L. J. Am. Chem. Soc. 2006, 128, 5279. doi: 10.1021/ja060140u
16. [16]
  Mohan, B.; Park, J. C.; Park, K. H. ChemCatChem 2016, 8, 2345. doi: 10.1002/cctc.201600280
17. [17]
  Zeng, X.; Gong, C.; Guo, H.; Xu, H.; Zhang, J.; Xie, J. New J. Chem. 2018, 42, 17346. doi: 10.1039/C8NJ03708F
18. [18]
  Perez-Mayoral, E.; Matos, I.; Fonseca, I.; Cejka, J. Chem.-Eur. J. 2010, 16, 12079. doi: 10.1002/chem.201001593
19. [19]
  Francesco, I. N.; Cacciuttolo, B.; Pucheault, M.; Antoniotti, S. Green Chem. 2015, 17, 837. doi: 10.1039/C4GC01990C
20. [20]
  Ma, Z.; Xie, F.; Yu, H.; Zhang, Y.; Wu, X.; Zhang, W. Chem. Commun. 2013, 49, 5292. doi: 10.1039/c3cc42088d
21. [21]
  Peng, X.; Tong, B.; Hirao, H.; Chiba, S. Angew. Chem., Int. Ed. 2014, 53, 1959. doi: 10.1002/anie.201308617
22. [22]
  Ding, W.; Song, Q. Org. Chem. Front. 2016, 3, 14. doi: 10.1039/C5QO00289C
23. [23]
  Kobayashi, S.; Xu, P.; Endo, T.; Ueno, M.; Kitanosono, T. Angew. Chem., Int. Ed. 2012, 51, 12763. doi: 10.1002/anie.201207343
24. [24]
  Zhou, X.-F.; Sun, Y.-Y.; Wu, Y.-D.; Dai, J.-J.; Xu, J.; Huang, Y.; Xu, H.-J. Tetrahedron 2016, 72, 5691. doi: 10.1016/j.tet.2016.07.079
25. [25]
  Belhomme, M., Wang, D., Szabó, K. J. Org. Lett. 2016, 18, 2503. doi: 10.1021/acs.orglett.6b01132
26. [26]
  Ranu, B. C., Samanta, S. J. Org. Chem. 2003, 68, 7130. doi: 10.1021/jo0347821
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Nano Cu-CuFe2O4-Catalyzed Selective Reduction of α, β, γ, δ-Unsaturated Carbonyls in Alcohol Medium

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Nano Cu-CuFe₂O₄-Catalyzed Selective Reduction of α, β, γ, δ-Unsaturated Carbonyls in Alcohol Medium