研究论文

锆基路易斯酸催化γ-戊内酯与胺的反应研究

  • 孔庆山 ,
  • 李兴龙 ,
  • 许华建 ,
  • 傅尧
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  • a 合肥工业大学食品与生物工程学院 合肥 230601;
    b 中国科学技术大学化学系 合肥微尺度物质科学国家实验室 能源材料化学协同创新中心 中国科学院城市污染物转化重点实验室 安徽省生物质洁净能源重点实验室 合肥 230026

收稿日期: 2020-03-08

  修回日期: 2020-04-02

  网络出版日期: 2020-04-17

基金资助

国家重点研发项目(No.2018YFB1501604)、国家自然科学基金(No.21472033)、安徽省重点科研开发项目(No.201904a07020069)、中央高校基础研究基金资助项目.

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.

摘要

γ-戊内酯(GVL)是重要的生物质平台分子,将其转化为高附加值的化学品和燃料,具有重要的应用前景.介绍了一种在温和条件下通过还原胺化/环化反应,分别使用锆基路易斯酸催化剂Zr-P-O和ZrOCl2·8H2O,催化GVL与胺类化合物合成羟基酰胺类化合物和吡咯烷酮类化合物.特别值得一提的是,在无溶剂的情况下,均可以得到中等偏上的产物收率.该方法为GVL的应用研究进一步奠定了基础.

本文引用格式

孔庆山 , 李兴龙 , 许华建 , 傅尧 . 锆基路易斯酸催化γ-戊内酯与胺的反应研究[J]. 有机化学, 2020 , 40(7) : 2062 -2070 . DOI: 10.6023/cjoc202003008

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.

参考文献

[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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