Citation: Kong Qingshan, Li Xinglong, Xu Huajian, Fu Yao. Study on Reaction of γ-Valerolactone and Amine Catalyzed by Zirconium-Based Lewis Acids[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 2062-2070. doi: 10.6023/cjoc202003008 shu

Study on Reaction of γ-Valerolactone and Amine Catalyzed by Zirconium-Based Lewis Acids

Kong Qingshan ^a,b ,
Li Xinglong ^b ,
Xu Huajian ^a,, ,
Fu Yao ^b,,

a.
School of Food and Biological Engineering, University of Science and Technology of China, Hefei 230601
b.
Hefei National Laboratory for Physical Sciences at the Microscale, Collaborative Innovation Center of Chemistry for Energy Materials, Chinese Academy of Sciences Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei 230026

Corresponding author: Xu Huajian, hjxu@hfut.edu.cn Fu Yao, fuyao@ustc.edu.cn
Received Date: 8 March 2020
Revised Date: 2 April 2020
Available Online: 17 April 2020
Fund Project: Project supported by the National Key Research and Development Program of China (No. 2018YFB1501604), the National Natural Science Foundation of China (No. 21472033), the Key Research and Development Program Projects in Anhui Province (No. 201904a07020069), and the Fundamental Research Funds for the Central Universitiesthe Key Research and Development Program Projects in Anhui Province No. 201904a07020069the National Natural Science Foundation of China (No. 21472033the National Key Research and Development Program of China No. 2018YFB1501604

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γ-Valerolactone (GVL) is an important biomass platform molecule, it can be converted into high value-added chemicals and fuel, which has important application prospects. This article describes a method for the synthesis of hydroxyamides and pyrrolidones from GVL and amine compounds by reductive amination/cyclization reactions under mild conditions using zirconium-based Lewis acid catalysts Zr-P-O and ZrOCl₂·8H₂O, respectively. In particular, a moderately high product yield can be obtained with the absence of a solvent. This method further lays the foundation for the application research of GVL.
- γ-valerolactone,
- hydroxyamide,
- pyrrolidone,
- Lewis acid catalysis,
- zirconium-based catalyst
1. [1]
2. [2]
  (a) Paul, S. F. US 5697987, 1997.
  (b) Serrano-Ruiz, J. C.; Wang, D.; Dumesic, J. A. Green Chem.2010, 12, 574.
3. [3]
  Geilen, F. M.; Engendahl, B.; Harwardt, A.; Marquardt, W.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2010, 49, 5510.
4. [4]
  Mehdi, H.; Fábos, V.; Tuba, R.; Bodor, A.; Mika, L. T.; Horváth, I.T. Top. Catal. 2008, 48, 49.
5. [5]
  Lange, J. P.; Price, R.; Ayoub, P. M.; Louis, J.; Petrus, L.; Clarke, L.; Gosselink, H. Angew. Chem., Int. Ed. 2010, 49, 4479.
6. [6]
  (a) Bond, J. Q.; Alonso, D. M.; Wang, D.; West, R. M.; Dumesic, J.A. Science 2010, 327, 1110.
  (b) Bond, J. Q.; Martin Alonso, D.; West, R. M.; Dumesic, J. A.Langmuir 2010, 26, 16291.
7. [7]
  Lange, J. P.; Vestering, J. Z.; Haan, R. J. Chem. Commun. 2007, 33, 3488.
8. [8]
  (a) Fieser, M.; Fieser, L. F.; Toromanoff, E.; Hirata, Y.; Heymann, H.; Tefft, M.; Bhattacharya, S. J. Am. Chem. Soc. 1956, 78, 2825.
  (b) Newkome, G. R.; Baker, G. R.; Saunders, M.J.; Russo, P. S.; Gupta, V. K.; Yao, Z.; Miller, J. E.; Bouillion, K. J. Am. Chem. Soc.1986, 108, 752.
  (c) Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K.; Russo, P.S.; Saunders, M. J. J. Am. Chem. Soc. 1986, 108, 849.
9. [9]
  (a) Rodgers, S. J.; Ng, C. Y.; Raymond, K. N. J. Am. Chem. Soc.1985, 107, 4094.
  (b) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech, J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333.
10. [10]
  Tietze, L. F.; Brand, S.; Pfeiffer, T. Angew. Chem., Int. Ed. 1985, 24, 784.
11. [11]
12. [12]
  (a) Gresham, T. L.; Jansen, J. E.; Shaver, F. W.; Bankert, R. A.; Fiedorek, F. T. J. Am. Chem. Soc. 1951, 73, 3168.
  (b) Guo, W.; Gómez, J. E.; Martínez-Rodríguez, L.; Bandeira, N.A.; Bo, C.; Kleij, A. W. ChemSusChem 2017, 10, 1969.
13. [13]
  (a) Matsumoto, K.; Hashimoto, S.; Okamoto, T.; Otani, S.; Hayami, J. I. Chem. Lett. 1987, 16, 803.
  (b) Matsumoto, K.; Hashimoto, S.; Uchida, T.; Okamoto, T.; Otani, S. B. Chem. Soc. Jpn. 1989, 62, 3138.
14. [14]
  Chalid, M.; Heeres, H. J.; Broekhuis, A. A. J. Appl. Polym. Sci.2012, 123, 3556.
15. [15]
  (a) Das, S.; Addis, D.; Knöpke, L. R.; Bentrup, U.; Junge, K.; Brückner, A.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 9180.
  (b) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int.Ed. 2002, 41, 4526.
  (c) Du, X. L.; He, L.; Zhao, S.; Liu, Y. M.; Cao, Y.; He, H. Y.; Fan, K. N. Angew. Chem., Int. Ed. 2011, 123, 7961.
  (d) Gao, G.; Sun, P.; Li, Y.; Wang, F.; Zhao, Z.; Qin, Y.; Li, F. ACS Catal. 2017, 7, 4927.
16. [16]
  (a) Huang, Y.-B.; Dai, J.-J.; Deng, X.-J.; Qu, Y.-C.; Guo, Q.-X.; Fu, Y. ChemSusChem 2011, 4, 1578.
  (b) Touchy, A. S.; Hakim Siddiki, S. M. A.; Kon, K.; Shimizu, K.-I.ACS Catal. 2014, 4, 3045.
  (c) Vidal, J. D.; Climent, M. J.; Concepcion, P.; Corma, A.; Iborra, S.; Sabater, M. J. ACS Catal. 2015, 5, 5812.
  (d) Wei, Y.; Wang, C.; Jiang, X.; Xue, D.; Li, J.; Xiao, J.Chem.Commun. 2013, 49, 5408.
  (e) Sun, Z.; Chen, J.; Tu, T. Green Chem. 2017, 19, 789.
  (f) Ledoux, A.; Sandjong Kuigwa, L.; Framery, E.; Andrioletti, B.Green Chem. 2015, 17, 3251.
  (g) Du, X.-L.; He, L.; Zhao, S.; Liu, Y.-M.; Cao, Y.; He, H.-Y.; Fan, K.-N. Angew. Chem., Int. Ed. 2011, 50, 7815.
  (h) Ogiwara, Y.; Uchiyama, T.; Sakai, N. Angew. Chem., Int. Ed.2016, 55, 1864.
17. [17]
  (a) Mansoor, S. S.; Aswin, K.; Logaiya, K.; Sudhan, S. P. N. J.Saudi Chem. Soc. 2016, 20, 138.
  (b) Singh, R.; Jakhar, K.; Sharma, P. Chem. Sci. 2017, 6, 135.
  (c) Han, L.; Zhou, Z. Appl. Organomet. Chem. 2019, 33, e4755.
18. [18]
  Shi, M. S.; Cui, C.; Yin, W. P. Eur. J. Org. Chem. 2005, 11, 2379.
19. [19]
  Ghosh, R.; Maiti, S.; Chakraborty, A. Tetrahedron Lett. 2005, 46, 147.
20. [20]
  Sun, H. B.; Hua, R.M.; Yin, Y. W. Molecules 2006, 11, 263.
21. [21]
  Firouzabadi, H.; Iranpoor, N.; Jafarpour, M.; Ghaderi, A. J. Mol.Catal., A: Chem. 2006, 252, 150.
22. [22]
  Eftekhari-Sis, B.; Abdollahifar, A.; Hashemi, M. M.; Zirak, M. Eur.J. Org. Chem. 2006, 22, 5152.
23. [23]
  Zhang, Z. H.; Li, T. S.; Li, J. J. Catal. Commun. 2007, 8, 1615.
24. [24]
  Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2008, 73, 6029.
25. [25]
  Shen, W. L.; Wang, M.; Feng, J. J.; Tian, H. Tetrahedron Lett. 2008, 49, 4047.
26. [26]
  Gliozzi, G.; Innorta, A.; Mancini, A.; Bortolo, R.; Perego, C.; Ricci, M.; Cavani, F. Appl. Catal. B-Environ. 2014, 145, 24.
27. [27]
  Liao, Y.; Liu, Q.; Wang, T.; Long, J.; Ma, L.; Zhang, Q. Green Chem. 2014, 16, 3305.
28. [28]
  Li, F.; France, L. J.; Cai, Z.; Li, Y.; Liu, S.; Lou, H.; Li, X. Appl.Catal. B-Environ. 2017, 214, 67.
29. [29]
  Antonetti, C.; Melloni, M.; Licursi, D.; Fulignati, S.; Ribechini, E.; Rivas, S.; Galletti, A. M. R. Appl. Catal. B-Environ. 2017, 206, 364.
30. [30]
  Wu, C.; Luo, X.; Zhang, H.; Liu, X.; Ji, G.; Liu, Z.; Liu, Z. Green Chem. 2017, 19, 3525.
31. [31]
  (a) Burba, C.; Volland, H. G. US 4156779, 1979.
  (b) Nelson, S. G.; Spencer, K. L.; Cheung, W. S.; Mamie, S. J. Tetrahedron 2002, 58, 7081.
32. [32]
  Vollema, G.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1963, 82, 305.
33. [33]
  De Jonge A. P.; Van der Ven B. Recl. Trav. Chim. Pays-Bas 1965, 84, 1177.
34. [34]
  Xu, Z.; Yan, P.; Jiang H.; Liu, K.; Zhang, Z. C. Chin. J. Chem.2017, 35, 581.
35. [35]
  Lukeš, R.; Koblicova, Z.; Blaha, K. Chem. Commun. 1963, 28, 2182.
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