Paper
NJC
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W.-T. Chang, Y.-H. Chao, C.-W. Li, K.-L. Lin, J.-J. Wang,
S. R. Kumar and S. J. Lue, J. Power Sources, 2019, 414, 86–95.
D. A. Dikin, S. Stankovich, E. J. Zimney, R. D. Piner, G. H.
Dommett, G. Evmenenko, S. T. Nguyen and R. S. Ruoff,
Nature, 2007, 448, 457.
1
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0 M. Zhou, Y. Wang, Y. Zhai, J. Zhai, W. Ren, F. Wang and
S. Dong, Chem. – Eur. J., 2009, 15, 6116–6120.
1 H. W. Kim, H. W. Yoon, S.-M. Yoon, B. M. Yoo, B. K. Ahn,
Y. H. Cho, H. J. Shin, H. Yang, U. Paik and S. Kwon, Science,
2013, 342, 91–95.
1
2 L. G. Cançado, A. Jorio, E. M. Ferreira, F. Stavale, C. Achete,
R. Capaz, M. Moutinho, A. Lombardo, T. Kulmala and
A. C. Ferrari, Nano Lett., 2011, 11, 3190–3196.
Fig. 5 Reusability of the catalyst over five cycles.
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3 P. Feicht and S. Eigler, ChemNanoMat, 2018, 4, 244–252.
4 I. B. Andelkovic, S. Kabiri, E. Tavakkoli, J. K. Kirby, M. J.
McLaughlin and D. Losic, J. Cleaner Prod., 2018, 185, 97–104.
5 M. Ramezanzadeh, M. Asghari, B. Ramezanzadeh and
G. Bahlakeh, Chem. Eng. J., 2018, 337, 385–397.
[
BIMIP]BF and the Fe O NPs are the active catalyst species which
4 3 4
provide the Breslow intermediate and oxidation of the product.
The recyclability and reusability of the catalyst was studied
five times for the direct amidation of benzaldehyde with aniline.
The catalytic activity of the catalyst was slightly decreased after five
cycles owing to leaching of a trace amount of the NHC organo-
catalyst (Fig. 5).
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6 W. Xie and M. Huang, Energy Convers. Manage., 2018, 159,
42–53.
7 M. Zhang, Y.-H. Liu, Z.-R. Shang, H.-C. Hu and Z.-H. Zhang,
Catal. Commun., 2017, 88, 39–44.
Conclusions
18 H. Sharma, S. Sharma, C. Sharma, S. Paul and J. H. Clark,
Mol. Catal., 2019, 469, 27–39.
In summary, we reported a novel magnetic-GO/NHC nanocatalyst
that was characterized by means of TEM, SEM, UV-Vis, FTIR, XRD
and EDS analysis, and used as a base for the direct aerobic
amidation of benzaldehydes with a variety of amines under
solvent-free conditions for the first time. In addition, this catalyst
system was used for the intra- and intermolecular dehydrogena-
tive coupling of aldehydes with Michael acceptors. This catalyst
system provided an efficient method for the synthesis of a wide
scope of compounds in good yields under solvent-free conditions.
The catalyst system was recoverable and reusable over five
repetitive cycles without demonstrating significant loss of activity.
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9 C. Gan, T. Liang, W. Li, X. Fan and M. Zhu, Appl. Surf. Sci.,
2019, 491, 105–115.
0 P. Bradder, S. K. Ling, S. Wang and S. Liu, J. Chem. Eng.
Data, 2010, 56, 138–141.
1 J. Balapanuru, J. X. Yang, S. Xiao, Q. Bao, M. Jahan,
L. Polavarapu, J. Wei, Q. H. Xu and K. P. Loh, Angew. Chem.,
Int. Ed., 2010, 49, 6549–6553.
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2 Y.-K. Yang, C.-E. He, R.-G. Peng, A. Baji, X.-S. Du, Y.-L.
Huang, X.-L. Xie and Y.-W. Mai, J. Mater. Chem., 2012, 22,
5666–5675.
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3 P. Damlin, M. Suominen, M. Heinonen and C. Kvarnstr o¨ m,
Carbon, 2015, 93, 533–543.
4 L. U. Nordstrøm, H. Vogt and R. Madsen, J. Am. Chem. Soc.,
Conflicts of interest
2008, 130, 17672–17673.
There are no conflicts to declare.
5 F. T. Wong, P. K. Patra, J. Seayad, Y. Zhang and J. Y. Ying,
Org. Lett., 2008, 10, 2333–2336.
6 B. Zhou, J. Du, Y. Yang and Y. Li, Org. Lett., 2013, 15,
References
2934–2937.
1
D. R. Dreyer, S. Park, C. W. Bielawski and R. S. Ruoff, Chem. 27 R. Mentlein and E. Heymann, Biochem. Pharmacol., 1984,
Soc. Rev., 2010, 39, 228–240.
33, 1243–1248.
Y. Zhu, S. Murali, W. Cai, X. Li, J. W. Suk, J. R. Potts and 28 C. A. Montalbetti and V. Falque, Tetrahedron, 2005, 61,
2
R. S. Ruoff, Adv. Mater., 2010, 22, 3906–3924.
10827–10852.
3
4
S. Pei and H.-M. Cheng, Carbon, 2012, 50, 3210–3228.
29 P. Tang, Org. Synth., 2003, 81, 262–272.
S. Yang, L. Zhi, K. Tang, X. Feng, J. Maier and K. M u¨ llen, 30 E. Valeur and M. Bradley, Chem. Soc. Rev., 2009, 38, 606–631.
Adv. Funct. Mater., 2012, 22, 3634–3640.
J. H. Dumont, U. Martinez, K. Artyushkova, G. M. Purdy,
31 E. A. B. Kantchev, C. J. O’Brien and M. G. Organ, Angew.
Chem., Int. Ed., 2007, 46, 2768–2813.
5
A. M. Dattelbaum, P. Zelenay, A. Mohite, P. Atanassov and 32 Y. Du, T. Barber, S. E. Lim, H. S. Rzepa, I. R. Baxendale and
G. Gupta, ACS Appl. Nano Mater., 2019, 2, 1675–1682. A. Whiting, Chem.l Commun., 2019, 55, 2916–2919.
C. Liang, H. Qiu, Y. Han, H. Gu, P. Song, L. Wang, J. Kong, 33 R. Ray, A. S. Hazari, S. Chandra, D. Maiti and G. K. Lahiri,
D. Cao and J. Gu, J. Mater. Chem. C, 2019, 7, 2725–2733. Chem. – Eur. J., 2018, 24, 1067–1071.
R. Yuan, J. Yuan, Y. Wu, P. Ju, L. Ji, H. Li, L. Chen, H. Zhou 34 G. Pandey, S. Koley, R. Talukdar and P. K. Sahani, Org. Lett.,
and J. Chen, Colloids Surf., A, 2018, 547, 56–63. 2018, 20, 5861–5865.
6
7
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