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

  • Kong Qingshan ,
  • Li Xinglong ,
  • Xu Huajian ,
  • Fu Yao
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  • 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

Received date: 2020-03-08

  Revised date: 2020-04-02

  Online published: 2020-04-17

Supported by

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 Universities.

Abstract

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.

Cite this article

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

References

[1] (a) Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411.
(b) Gong, B.-X.; Yan, L.; Chen, M.-Y.; Deng, J.; Fu, Y. Chin. J. Org. Chem. 2017, 37, 3170(in Chinese). (龚宝祥, 严龙, 陈蒙远, 邓晋, 傅尧, 有机化学, 2017, 37, 3170.)
(c) Yang, Z.; Fu, Y.; Guo, Q.-X. Chin. J. Org. Chem. 2014, 34, 273(in Chinese). (杨珍, 傅尧, 郭庆祥, 有机化学, 2014, 34, 273.)
(d) Wang, H.-J.; Zhao, Y.; Wang, C.; Fu, Y.; Guo, Q.-X. Acta Chim. Sinica 2009, 67, 893(in Chinese). (王华静, 赵岩, 王晨, 傅尧, 郭庆祥, 化学学报, 2009, 67, 893.)
(e) Li, J.; Huang, Y.-B.; Guo, Q.-X.; Fu, Y. Acta Chim. Sinica 2014, 72, 1223(in Chinese) (李江, 黄耀兵, 郭庆祥, 傅尧, 化学学报, 2014, 72, 1223.)
(f) Xu, J.; Fan, W.-G.; Popowycz, F.; Queneau, Y.; Gu, Y.-L. Chin. J. Org. Chem. 2019, 39, 2131(in Chinese). (徐静, 范维刚, 波波维奇•弗洛伦斯, 葛诺伊夫, 顾彦龙, 有机化学, 2019, 39, 2131.)
[2] (a) Paul, S. F. US 5697987, 1997.
(b) Serrano-Ruiz, J. C.; Wang, D.; Dumesic, J. A. Green Chem. 2010, 12, 574.
[3] Geilen, F. M.; Engendahl, B.; Harwardt, A.; Marquardt, W.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2010, 49, 5510.
[4] Mehdi, H.; Fábos, V.; Tuba, R.; Bodor, A.; Mika, L. T.; Horváth, I. T. Top. Catal. 2008, 48, 49.
[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] (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] Lange, J. P.; Vestering, J. Z.; Haan, R. J. Chem. Commun. 2007, 33, 3488.
[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] (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] Tietze, L. F.; Brand, S.; Pfeiffer, T. Angew. Chem., Int. Ed. 1985, 24, 784.
[11] (a) Hellberg, L. H.; Beeson, C.; Somannathan, R. Tetrahedron Lett. 1986, 3955.
(b) Sakai, K.; Oisaki, K.; Kanai, M. Adv. Synth. Catal. 2019.
(c) Qi, J.; Sun, C.; Tian, Y.; Wang, X.; Li, G.; Xiao, Q.; Yin, D. Org. Lett. 2014, 16, 190.
(d) Yao, Y.; Li, W.-D.; Tong, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2015, 35, 223(in Chinese). (姚远, 李伟东, 仝文婷, 陈建新, 有机化学, 2015, 35, 223.)
(e) Chen, C.; Xu, S.-S.; Liu, W.-B. Chin. J. Org. Chem. 2016, 36, 1890(in Chinese). (陈翠, 徐松森, 刘卫兵, 有机化学, 2016, 36, 1890.)
[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] (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] Chalid, M.; Heeres, H. J.; Broekhuis, A. A. J. Appl. Polym. Sci. 2012, 123, 3556.
[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] (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] (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] Shi, M. S.; Cui, C.; Yin, W. P. Eur. J. Org. Chem. 2005, 11, 2379.
[19] Ghosh, R.; Maiti, S.; Chakraborty, A. Tetrahedron Lett. 2005, 46, 147.
[20] Sun, H. B.; Hua, R.M.; Yin, Y. W. Molecules 2006, 11, 263.
[21] Firouzabadi, H.; Iranpoor, N.; Jafarpour, M.; Ghaderi, A. J. Mol. Catal., A: Chem. 2006, 252, 150.
[22] Eftekhari-Sis, B.; Abdollahifar, A.; Hashemi, M. M.; Zirak, M. Eur. J. Org. Chem. 2006, 22, 5152.
[23] Zhang, Z. H.; Li, T. S.; Li, J. J. Catal. Commun. 2007, 8, 1615.
[24] Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2008, 73, 6029.
[25] Shen, W. L.; Wang, M.; Feng, J. J.; Tian, H. Tetrahedron Lett. 2008, 49, 4047.
[26] Gliozzi, G.; Innorta, A.; Mancini, A.; Bortolo, R.; Perego, C.; Ricci, M.; Cavani, F. Appl. Catal. B-Environ. 2014, 145, 24.
[27] Liao, Y.; Liu, Q.; Wang, T.; Long, J.; Ma, L.; Zhang, Q. Green Chem. 2014, 16, 3305.
[28] Li, F.; France, L. J.; Cai, Z.; Li, Y.; Liu, S.; Lou, H.; Li, X. Appl. Catal. B-Environ. 2017, 214, 67.
[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] Wu, C.; Luo, X.; Zhang, H.; Liu, X.; Ji, G.; Liu, Z.; Liu, Z. Green Chem. 2017, 19, 3525.
[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] Vollema, G.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1963, 82, 305.
[33] De Jonge A. P.; Van der Ven B. Recl. Trav. Chim. Pays-Bas 1965, 84, 1177.
[34] Xu, Z.; Yan, P.; Jiang H.; Liu, K.; Zhang, Z. C. Chin. J. Chem. 2017, 35, 581.
[35] Lukeš, R.; Koblicova, Z.; Blaha, K. Chem. Commun. 1963, 28, 2182.
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