Abstract
Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS 13C NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer–Emmett–Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A3-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product.
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E. Doustkhah, J. Lin, S. Rostamnia, C. Len, R. Luque, X. Luo, Y. Bando, K.C.-W. Wu, J. Kim, Y. Yamauchi, Y. Ide, Chem. Eur. J. 25, 1614 (2019)
L.-Y. Xie, S. Peng, L.-H. Lu, J. Hu, W.-H. Bao, F. Zeng, Z. Tang, X. Xu, W.-M. He, ACS Sustain. Chem. Eng. 6, 7989 (2018)
C. Wu, L.-H. Lu, A.-Z. Peng, G.-K. Jia, C. Peng, Z. Cao, Z. Tang, W.-M. He, X. Xu, Green Chem. 20, 3683 (2018)
L.-H. Lu, Z. Wang, W. Xia, P. Cheng, B. Zhang, Z. Cao, W.-M. He, Chin. Chem. Lett. 30, 1237 (2019)
J.H. Clark, Acc. Chem. Res. 35, 791 (2002)
L.M. Gilbertson, J.B. Zimmerman, D.L. Plata, J.E. Hutchison, P.T. Anastas, Chem. Soc. Rev. 44, 5758 (2015)
M. Vafaeezadeh, H. Alinezhad, J. Mol. Liq. 218, 95 (2016)
R. Ratti, Adv. Chem. 2014, 1 (2014)
A. Riisager, R. Fehrmann, M. Haumann, P. Wasserscheid, Eur. J. Inorg. Chem. 2006, 695 (2006)
G. Busca, Chem. Rev. 107, 5366 (2007)
A.F. Lee, J.A. Bennett, J.C. Manayil, K. Wilson, Chem. Soc. Rev. 43, 7887 (2014)
H.R. Shaterian, A. Hosseinian, Res. Chem. Intermed. 40, 3011 (2014)
H.-P. Steinrück, P. Wasserscheid, Catal. Lett. 145, 380 (2015)
R. Skoda-Földes, Molecules 19, 8840 (2014)
L.L. Chng, N. Erathodiyil, J.Y. Ying, Acc. Chem. Res. 46, 1825 (2013)
A. Ramazani, M. Abrvash, S. Sadighian, K. Rostamizadeh, M. Fathi, Res. Chem. Intermed. 44, 7891 (2018)
P. Das, S. Ganguly, S. Banerjee, N.C. Das, Res. Chem. Intermed. 45, 3823 (2019)
Y. Chen, C. Tan, H. Zhang, L. Wang, Chem. Soc. Rev. 44, 2681 (2015)
H.Y. Hafeez, S.K. Lakhera, P. Karthik, M. Anpo, B. Neppolian, Appl. Surf. Sci. 449, 772 (2018)
R. Garg, N.K. Dutta, N.R. Choudhury, Nanomaterials 4, 267 (2014)
H.D. Hanoon, E. Kowsari, M. Abdouss, H. Zandi, M.H. Ghasemi, Res. Chem. Intermed. 43, 1751 (2017)
P. Marion, B. Bernela, A. Piccirilli, B. Estrine, N. Patouillard, J. Guilbot, F. Jérôme, Green Chem. 19, 4973 (2017)
S. Narwal, S. Kumar, P.K. Verma, Res. Chem. Intermed. 43, 2765 (2017)
R.H.F. Manske, M. Kukla, Org. React. 7, 59 (1953)
S.E. Denmark, S. Venkatraman, J. Org. Chem. 71, 1668 (2006)
P. Friedlander, C.F. Gohring, Ber 16, 1833 (1883)
J.A. Knight, H.K. Porter, P.K. Calaway, J. Am. Chem. Soc. 66, 1893 (1944)
R.H. Reitsema, Chem. Rev. 43, 47 (1948)
F.W. Bergstrom, Chem. Rev. 35, 156 (1944)
Y. Zhang, P. Li, L. Wang, J. Heterocycl. Chem. 48, 153 (2011)
Y. Kuninobu, Y. Inoue, K. Takai, Chem. Lett. 36, 1422 (2007)
H.Z. Sueda Huma, R. Halder, S.S. Kalra, J. Das, J. Iqbal, Tetrahedron Lett. 43, 6485 (2002)
R. Kurane, J. Jadhav, S. Khanapure, R. Salunkhe, G. Rashinkar, Green Chem. 15, 1849 (2013)
S. Khanapure, M. Jagadale, R. Salunkhe, G. Rashinkar, Res. Chem. Intermed. 42, 2075 (2016)
W.S. Hummers, R.E. Offeman, J. Am. Chem. Soc. 80, 1339 (1958)
M. Fang, K. Wang, H. Lu, Y. Yang, S. Nutt, J. Mater. Chem. 19, 7098 (2009)
S. Gajare, A. Patil, D. Kale, P. Bansode, P. Patil, G. Rashinkar, Catal. Lett. 150, 243 (2019)
H. Naeimi, Z. Ansarian, Inorg. Chim. Acta 466, 417 (2017)
C.Y. Lee, Q.V. Le, C. Kim, S.Y. Kim, Phys. Chem. Chem. Phys. 17, 9369 (2017)
K. Miyatake, H. Iyotani, K. Yamamoto, E. Tsuchida, Macromolecules 29, 6969 (1996)
R. Langner, G. Zundel, J. Phys. Chem. 99, 12214 (1995)
J. Ji, G. Zhang, H. Chen, S. Wang, G. Zhang, F. Zhang, X. Fan, Chem. Sci. 2, 484 (2011)
T.M.G. Mohiuddin, A. Lombardo, R.R. Nair, A. Bonetti, G. Savini, R. Jalil, N. Bonini, D.M. Basko, C. Galiotis, N. Marzari, K.S. Novoselov, A.K. Geim, A.C. Ferrari, Phys. Rev. B 79, 205433 (2009)
A.C. Ferrari, J.C. Meyer, V. Scardaci, C. Casiraghi, M. Lazzeri, F. Mauri, S. Piscanec, D. Jiang, K.S. Novoselov, S. Roth, A.K. Geim, Phys. Rev. Lett. 97, 187401 (2006)
S.H. Lee, D.R. Dreyer, J. An, A. Velamakanni, R.D. Piner, S. Park, Y. Zhu, S.O. Kim, C.W. Bielawski, R.S. Ruoff, Macromol. Rapid Commun. 31, 281 (2010)
S. Ayyaru, Y.H. Ahn, J MembSci. 525, 210 (2017)
M.G. Rabbani, H.M. El-Kaderi, Chem. Mater. 24, 1511 (2012)
V. Panwar, K. Cha, J.O. Park, S. Park, Sens. Actuators B Chem. 161, 460 (2011)
M. Saikia, L. Saikia, RSC Adv. 6, 15846 (2016)
Q. Dong, X. Zhuang, Z. Li, B. Li, B. Fang, C. Yang, H. Xie, F. Zhang, X. Feng, J. Mater. Chem. A 3, 7767 (2015)
L. Jiao, Y. Hu, H. Ju, C. Wang, M.-R. Gao, Q. Yang, J. Zhu, S.-H. Yu, H.L. Jiang, J. Mater. Chem. A 5, 23170 (2017)
W. Ai, W. Zhou, Z. Du, Y. Du, H. Zhang, X. Jia, L. Xie, M. Yi, T. Yu, W. Huang, J. Mater. Chem. 22, 23439 (2012)
Q. Huang, L. Zhou, X. Jiang, Y. Zhou, H. Fan, W. Lang, A.C.S. Appl, Mater. Interfaces 6, 13502 (2014)
M. Brahmayya, S.A. Dai, S.Y. Suen, Sci. Rep. 7, 4675 (2017)
A. Kulkarni, B. Torok, Green Chem. 12, 875 (2010)
G.M. Ziarani, A. Badiei, N.H. Mohatasham, N. Lashgiri, J. Chil. Chem. Soc. 59, 2271 (2014)
H. Sharghi, M. Aberi, J. Aboonajmi, J. Iran. Chem. Soc. 13, 2229 (2016)
W. Wu, Y. Guo, X. Xu, Z. Zhou, X. Zhang, B. Wu, W. Yi, Organ. Chem. Front. 5, 1713 (2018)
Acknowledgements
We gratefully acknowledge Indian Institute of Bombay (IITB), North-Eastern Hill University Shillong (NEHU), Indian Institute of Technology, Madras (IITM) for providing spectral facilities and Shivaji University Kolhapur for providing financial assistance and Golden Jubilee Research Fellowship (GJRF).
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Gajare, S., Patil, A., Hangirgekar, S. et al. Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Brønsted acidic ionic liquid. Res Chem Intermed 46, 2417–2436 (2020). https://doi.org/10.1007/s11164-020-04099-7
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DOI: https://doi.org/10.1007/s11164-020-04099-7