Supported Ionic Liquid H2PMo12O40-NMPIL@SiO2 as an Efficient Catalyst for Alkylation of Indoles with Epoxides or Alcohols under Mild Conditions

Authors

  • Jin Tan China Three Gorges University
  • Dong Fang Yancheng Teachers University
  • Yu Lin Hu China Three Gorges University

DOI:

https://doi.org/10.29356/jmcs.v62i1.584

Keywords:

Supported ionic liquid, alkylation, indoles, 3-alkylindoles, heterogeneous catalysis

Abstract

3-Alkylindoles have been prepared in 91~99% excellent yields by alkylation of indoles with epoxides or alcohols catalyzed by the recyclable heteropoly acid based supported functionalized ionic liquid H2PMo12O40-NMPIL@SiO2 under heterogeneous catalysis atroom temperature. The influence of various reaction parameters including catalyst selection, catalyst amount, reaction time, solvent, and reaction temperature were studied. The heterogeneous supported catalyst was easily recoverable by filtration, and could be used for six consecutive runs without significant loss in catalytic activity. This study demonstrated a green and highly efficient chemistry technology in the preparation of 3-alkylindoles.

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Author Biographies

Jin Tan, China Three Gorges University

College of Materials and Chemical Engineering, Key laboratory of inorganic nonmetallic crystalline and energy conversion materials

Dong Fang, Yancheng Teachers University

College of Chemistry and Environmental Engineering

Yu Lin Hu, China Three Gorges University

College of Materials and Chemical Engineering, Key laboratory of inorganic nonmetallic crystalline and energy conversion materials

References

Bartoli, G.; Dalpozzo, R.; Nardi, M. Chem. Soc. Rev. 2014, 43, 4728-4750.

Kiamehr, M.; Moghaddam, F. M.; Erami, M. S. Tetrahedron Lett. 2015, 56, 7190-7192.

Anderson, L. L.; Kroc, M. A.; Reidl, T. W.; Son, J. J. Org. Chem. 2016, 81, 9521-9529.

Zhang, C.; Qu, Y.; Niu, B. Bioorgan. Med. Chem. 2016, 24, 5781-5786.

Chen, Y.; Xie, Z. Chin. J. Org. Chem. 2012, 32, 462-471.

Bandini, M.; Umani-Ronchi, A. Catalytic asymmetric Friedel-Crafts alkylations, Wiley-VCH, Weinheim, 2009.

Bhadury, P. S.; Pang, J. Curr. Org. Chem. 2014, 18, 2108-2124.

Xu, F.; Huang, D.; Han, C.; Shen, W.; Lin, X.; Wang, Y. J. Org. Chem. 2010, 75, 8677-8680.

Hui, Y. H.; Chen, Y. C.; Gong, H. W.; Xie, Z. F. Chin. Chem. Lett. 2014, 25, 163-165.

Li, W. J. Catal. Commun. 2014, 52, 53-56.

Arai, T.; Awata, A.; Wasai, M.; Yokoyama, N.; Masu, H. J. Org. Chem. 2011, 76, 5450-5456.

Subramanian, T.; Kumarraja, M.; Pitchumani, K. J. Mol. Catal. A: Chem. 2012, 363-364, 115-121.

Blay, G.; Cano, J.; Cardona, L.; Fernández, I.; Muñoz, M. C.; Pedro, J. R.; Vila, C. J. Org. Chem. 2012, 77, 10545-10556.

Adachi, S.; Tanaka, F.; Watanabe, K.; Harada, T. Org. Lett. 2009, 11, 5206-5209.

Taheri, A.; Lai, B.; Cheng, C.; Gu, Y. Green Chem. 2015, 17, 812-816.

Downey, C. W.; Poff, C. D.; Nizinski, A. N. J. Org. Chem. 2015, 80, 10364-10369.

Kubczyk, T. M.; Williams, S. M.; Kean, J. R.; Davies, T. E.; Taylor, S. H.; Graham, A. E. Green Chem. 2011, 13, 2320-2325.

Khorshidi, A. Ultrason. Sonochem. 2012, 19, 570-575.

Das, B.; Thirupathi, P.; Kumar, R. A.; Reddy, K. R. Catal. Commun. 2008, 9, 635-638.

Bandgar, B. P.; Patil, A. V. Tetrahedron Lett. 2007, 48, 173-176.

Naveen, R. P.; Babu, S. A. Catal. Commun. 2012, 29, 118-121.

Hikawa, H.; Suzuki, H.; Azumaya, I. J. Org. Chem. 2013, 78, 12128-12135.

Cano, R.; Yus, M.; Ramón, D. J. Tetrahedron Lett. 2013, 54, 3394-3397.

Robertson, F. J.; Kenimer, B. D.; Wu, J. Tetrahedron 2011, 67, 4327-4332.

Putra, A. E.; Takigawa, K.; Tanaka, H.; Ito, Y. ; Oe, Y.; Ohta, T. Eur. J. Org. Chem. 2013, 6344-6354.

Zou, K.; Ye, J.; Wu, X. Y. Tetrahedron 2015, 71, 7869-7873.

George, J.; Reddy, B. V. S. Org. Biomol. Chem. 2012, 10, 4731-4738.

García-García, C.; Ortiz-Rojano, L.; Álvarez, S.; Álvarez, R.; Ribagorda, M.; Carreño, M. C. Org. Lett. 2016, 18, 2224-2227.

Yao, S. J.; Ren, Z. H.; Wang, Y. Y.; Guan, Z. H. J. Org. Chem. 2016, 81, 4226-4234.

Wu, J.; Wang, D.; Wu, F.; Wan, B. J. Org. Chem. 2013, 78, 5611-5617.

Wolf, C.; Zhang, P. Adv. Synth. Catal. 2011, 353, 760-766.

de Nanteuil, F.; Loup, J.; Waser, J. Org. Lett. 2013, 15, 3738-3741.

Chen, Q. A.; Klare, H. F. T.; Oestreich, M. J. Am. Chem. Soc. 2016, 138, 7868-7871.

Goossens, K.; Lava, K.; Bielawski, C. W.; Binnemans, K. Chem. Rev. 2016, 116, 4643-4807.

Doherty, A. P.; Patterson, S.; Diaconu, L.; Graham, L.; Barhdadi, R.; Puchelle, V.; Wagner, K.; Office, D. L.; Chen, J.; Wallace, G. G. J. Mex. Chem. Soc. 2015, 59, 263-268; Martínez-Palou, R. J. Mex. Chem. Soc. 2007, 51, 252-264.

Zare, A.; Khanivar, R.; Hatami, M.; Mokhlesi, M.; Zolfigol, M. A.; Moosavi-Zare, A. R.; Hasaninejad, A.; Khazaei, A.; Khakyzadeh, V. J. Mex. Chem. Soc. 2012, 56, 389-394; Leticia G. R.; Ignacio, A. R. J. Mex. Chem. Soc. 2012, 56, 201-206.

Lin, J. H.; Zhang, C. P.; Zhu, Z. Q.; Chen, Q. Y.; Xiao, J. C. J. Fluorine Chem. 2009, 130, 394-398.

Pohako-Esko, K.; Bahlmann, M.; Schulz, P. S.; Wasserscheid, P. Ind. Eng. Chem. Res. 2016, 55, 7052-7059.

Jadhav, A. H.; Thorat, G. M.; Lee, K.; Lim, A. C.; Kang, H.; Seo, J. G. Catal. Today 2016, 265, 56-67.

Kim, M. I.; Choi, S. J.; Kim, D. W.; Park, D. W. J. Ind. Eng. Chem. 2014, 20, 3102-3107.

Li, M.; Zhang, M.; Wei, A.; Zhu, W.; Xun, S.; Li, Y.; Li, H. J. Mol. Catal. A: Chem. 2015, 406, 23-30.

Xin, B.; Hao, J. Chem. Soc. Rev. 2014, 43, 7171-7187.

Agrigento, P.; Al-Amsyar, S. M.; Sorée, B.; Taherimehr, M.; Gruttadauria, M.; Aprile, C.; Pescarmona, P. P. Catal. Sci. Technol. 2014, 4, 1598-1607.

Zhang, J.; Zheng, Y.; Lan, L.; Yu, P.; Shi, W.; Li, J.; Tan, Y. Chin. J. Org. Chem. 2011, 31, 1076-1080.

Zhao, Z.; Li, N.; Bhutto, A. W.; Abdeltawab, A. A.; Al-Deyab, S. S.; Liu, G.; Chen, X.; Yu, G. Sci. China Chem. 2016, 59, 564-570.

Guo, H.; Li, X.; Wang, J. L.; Jin, X. H.; Lin, X. F. Tetrahedron 2010, 66, 8300-8303.

Hu, Y. L.; Fang, D. J. Mex. Chem. Soc. 2016, 60, 207-217.

Zhang, L.; Xian, M.; He, Y.; Li, L.; Yang, J.; Yu, S.; Xu, X. Bioresource Technol. 2009, 100, 4368-4373.

Zhang, W.; Leng, Y.; Zhu, D.; Wu, Y.; Wang, J. Catal. Commun. 2009, 11, 151-154.

Ayati, A.; Ahmadpour, A.; Bamoharram, F. F.; Heravi, M. M.; Sillanpää, M. Gold Bull. 2012, 45, 145-151.

Aldrich. Aldrich handbook- a catalog of fine chemicals and laboratory equipment, Sigma-Aldrich Chemical Co., Milwaukee, 2012-2014.

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Published

2018-05-25

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Regular Articles