Efficient synthesis of aryl amines from aryl halides in the presence of melamine-supported CuO nanocatalyst in water

Document Type : Original Article

Authors

1 Department of chemistry, Faculty of science, Shahrekord university, Shahrekord, Iran

2 Department of chemistry, College of science, Shahrekord university, Shahrekord, Iran

3 Department of chemistry, College of science, Shahrekord university

10.22036/cr.2020.242339.1120

Abstract

In this research, an efficient procedure is reported for the synthesis of aryl amines from aryl halides using aqueous ammonia in the presence of melamine-supported CuO nanocatalyst (M-CuO-nanocatalyst) in water. The catalyst was prepared by co-precipitation method and characterized by various techniques such as SEM, EDS, TGA, XRD , XRF, and BET analysis.Various aryl halides reacted with aqueous ammonia and corresponding aryl amines were obtained in relatively short reaction times and high yields. M-CuO-nanocatalyst is a stable, safe and high performance catalyst that working with it is easy. It can be easily separated from the reaction medium. M-CuO nanocatalyst is easily prepared, easy to handle and recyclable and up to 6 consecutive runs catalyzes the synthesis of aryl amines well. It could be reused more than 6 times without considerable loss of its initial activity. Furthermore, heterogeneous reaction conditions, clean procedure, simple work-up, high yields of products and short reaction times are other advantages of this method.

Graphical Abstract

Efficient synthesis of aryl amines from aryl halides in the presence of melamine-supported CuO nanocatalyst in water

Keywords

References

1) K. Y. Law, Chem. Rev. 93, 449 (1993)
2) D. M.Roundhill, Chem. Rev. 92, 1 (1992)
3) S. Park, A. L. Rheingold, D. M. Roundhill, Organometallics. 10, 615 (1991)
4) S. Jiang, X. Dong, Y. Qiu, D. Chen, X. Wu, S. Jiang, Tetrahedron. Lett. 61, 151683 (2020)
5) M. Takagi, A. Watanabe, S. Murata, R. Takita, Org. Biomol. Chem. 17, 1791 (2019)
6) J. Gao, S. Bhunia, K. Wang, L. Gan, S. Xia, D. Ma, Org. Lett. 19, 2809 (2017)
7) H. S. Jung, T. Yun, Y. Cho, H. B. Jeon, Tetrahedron. 72, 5988 (2016)
8) N. Noori, M. Nikoorazm, A. Ghorbani-Choghamarani. Catal. Lett. 147, 204 (2017)
9) A. Naghipour, A. Ghorbani-Choghamarani, H. Babaee, M. Hashemi, B. Notash, J. Organometa. Chem. 841, 31 (2017)
10) A. Ghorbani-Choghamarani, A. Naghipour, F. Heidarizadi, R. Shirkhani, B. Notash, Inorganica. Chim. Acta. 446, 97 (2016)
11) H.S. Jung, T. Yun, Y. Cho, H.B. Jeon, Tetrahedron. 72, 5988 (2016)
12) X. Wang, F. Meng, J. Zhang, J. Xie, B. Dai, Catal Lett. 148, 1142 (2018)
13) S. S. Chavan, S. K. Sawan, V. A. Sawant, G. K. Lahiri, Inorg Chem Commun. 14, 1373 (2011)
14) B.Yang, L. Liao, Y. Zeng, X. Zhu, Y. Wan, Catal Commun. 45, 100 (2014)
15) A. Sirvastava, N. Jain, Tetrahedron. 69, 5092 (2013)
16) A. Ghorbani-Choghamarani, B. Tahmasbi, N. Noori, R. Ghafouri-najad, J. Iran. Chem. Soc. 14, 681 (2017)
17) S. Scgauermann, N. Nilius, S. Shaikhutdinov, H.J. Freund, Acc. Chem. Res. 46, 1673 (2013)
18) B. Gerard, J. Ryan, A.B. Beeler, J.A. Porco, Tetrahedron. 62, 6405 (2006)
19) M. Rajabi, J. Albadi, A. R, Momeni, Res. Chem. Intermed. 46, 3879 (2020)
20) J. Albadi, A. Alihoseinzadeh, A. Razeghi, Catal. Commun. 49, 1 (2014)
21) J. Albadi, A. Alihoseinzadeh, M. Jalali, M. Shahrezaei, A. Mansournezhad, Mol. Catal. 440, 133 (2017)
22) J. Albadi, A. Mansournezhad, Chin. J. Chem. 32, 396 (2014)
23) J. Albadi, M. Jalali, H.A. Samimi, Catal. Lett. 148, 3750 (2018)
24) J. Albadi, H.A. Samimi, A. R, Momeni, Chem. Methodol. 4, 565 (2020)
Iranian Journal of Chemistry
Volume 3, Issue 2 - Serial Number 5
March 2021
Pages 213-218

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History

  • Receive Date: 04 August 2020
  • Revise Date: 25 October 2020
  • Accept Date: 07 December 2020

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