SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 6: 1792 - 1798

DOI: https://doi.org/10.6023/cjoc202112014

ARTICLES

Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction

  • Huili Liu ,
  • Chaojie Zhu ,
  • Tiandi Tang
Expand
  • a School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
    b School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189
*E-mail: ;

Received date: 2021-12-06

  Revised date: 2022-01-12

  Online published: 2022-02-25

Supported by

National Natural Science Foundation of China(21776022); National Natural Science Foundation of China(22178029)

Fold

Abstract

The Friedel-Crafts alkenylation of various alkynes and electron-rich arenes was achieved under mild conditions by using acidic zeolite Hbeta as catalyst. HBeta possesses Lewis acid sites (LAS) and Bronsted acid sites (BAS), which are adsorption activation sites and protonation sites for alkynes, respectively. Preliminary studies have shown that the reaction proceeds through a BAS-promoted alkenyl cation process. The strong interaction between the alkenyl cation and BAS prevents the highly reactive alkenyl cation from polymerizing, avoiding the formation of oligomerized by-products. HBeta, as a heterogeneous catalyst, showed excellent reproducibility in the alkyne alkenylation reaction and could be recycled at least 5 times without significant loss of activity. Finally, according to the experimental results, the reaction mechanism of HBeta-catalyzed alkyne alkenylation was proposed.

Key words： HBeta zeollite; alkyne; Friedel-Crafts alkenylation reaction; alkenyl cation

Cite this article

Huili Liu , Chaojie Zhu , Tiandi Tang . Acidic Zeolite HBeta Catalyzed Friedel-Crafts Alkenylation Reaction[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1792 -1798 . DOI: 10.6023/cjoc202112014

References

[1]
(a) Chinchilla, R.; Nájera, C. Chem. Rev. 2014, 114, 1783.
[1]
(b) Lee, M. T.; Lalic, G. J. Am. Chem. Soc. 2021, 143, 16663.
[2]
(a) Meijere, A. D.; Meyer, F. E. Angew. Chem., Int. Ed. 1994, 33, 2379.
[2]
(b) Belteskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
[3]
Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
[4]
(a) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
[4]
(b) Edwards, J. T.; Merchant, R. R.; McClymont, K. S.; Knouse, K. W.; Qin, T.; Malins, L. R.; Vokits, B.; Shaw, S. A.; Bao, D.-H.; Wei, F.-L.; Zhou, T.; Eastgate, M. D.; Baran, P. S. Nature 2017, 545, 213.
[4]
(c) Gunnoe, T. B.; Schinski, W. L.; Jia, X.; Zhu, W. ACS Catal. 2020, 10, 14080.
[4]
(d) Zhou, F.; Li, M.; Jiang, H.; Wu, W. Adv. Synth. Catal. 2021, 363, 4841.
[5]
Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485, 3485.
[6]
Tokunaga, Y.; Sakakura, T.; Tanaka, M. Mol. Catal. 1989, 56, 305.
[7]
Werner, H.; Hohn, A.; Dziallas, M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1090.
[8]
Tsuchimoto, T.; Maeda, T.; Shirakara, E.; Karakami, Y. Chem. Commun. 2000, 1573.
[9]
(a) Jia, C.-G.; Piao, D.-G.; Oyamada, J.; Lu, W.-J.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
[9]
(b) Jia, C.-G.; Piao, D.-G.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
[10]
Song, C. E.; Jung, D. U; Choung, S. Y.; Roh, E. J.; Lee, S. G. Angew. Chem., Int. Ed. 2004, 43, 6183.
[11]
Yoon, M. Y.; Kim, J. H.; Choi, D. S.; Shin, U. S.; Lee, J. Y.; Song, C. E. Adv. Synth. Catal. 2007, 349, 1725.
[12]
Jia, C.-G.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 63.
[13]
(a) Haldar, S.; Koner, S. Beilstein J. Org. Chem. 2013, 9, 49.
[13]
(b) Zhao, Z.-K.; Wang, X.-H. Appl. Catal., 2015, 503, 103.
[13]
(c) Zhao, Z.-K.; Wang, X.-H. Appl. Catal., 2016, 526, 139.
[13]
(d) Zhao, Z.-K.; Ran, J.-F.; Jiao, Y.-H.; Li, W.-Z.; Miao, B.-Y. Appl. Catal., 2016, 513, 1.
[14]
(a) Liu, L.-C.; Corma, A. Chem. Rev. 2018, 118, 4981.
[14]
(b) Dusselier, M.; Davis, M. E. Chem. Rev. 2018, 118, 5265.
[14]
(c) Chen, L.-H.; Sun, M.-H.; Wang, Z.; Yang, W.-M.; Xie, Z.-K.; Su, B.-L. Chem. Rev. 2020, 120, 11194.
[15]
(a) Zhang, Q.; Yu, J.-H.; Corma, A. Adv. Matter. 2020, 32, 2002927.
[15]
(b) Gordon, C. P.; Engler, H.; Tragl, A. S.; Plodinec, M.; Lunkenbein, T.; Berkessel, A.; Teles, J. H.; Parvulescu, A. N.; Copéret, C. Nature 2020, 586, 708.
[15]
(c) Jin, Z.; Wang, L.; Zuidema, E.; Mondal, K.; Zhang, M.; Zhang, J.; Xiao, F.-S. Science 2020, 367, 193.
[16]
(a) Xie, B.; Song, J.; Ren, L.; Ji, Y.; Li, J.; Xiao, F.-S. Chem. Mater. 2008, 20, 4533.
[16]
(b) Escola, J. M.; Serrano, D. P.; Sanz, R.; Garcia, R. A.; Peral, A.; Moreno, I.; Linares, M. Catal. Today 2018, 304, 89.
[17]
Fu, W.-Q.; Shen, R.-S.; Bai, E.-H.; Zhang, L.; Chen, Q.; Fang, Z.-X.; Li, G.-C.; Yi, X.-F.; Zheng, A.-M.; Tang, T.-T. ACS Catal. 2018, 8, 9043.
[18]
Zhao, Z.-K.; Dai, Y.-T.; Bao, T.; Li, R.-Z.; Wang, G.-R. J. Catal. 2012, 288, 44.
[19]
Rhodes, C. J. J. Chem. Soc., Faraday Trans. 1991, 87, 3179.
Options
Outlines

/

〈 〉