Copper Catalyzed Synthesis of Aryl Azides from Aryl Bromides and Sodium Azide

Ming Zeng; Yu Hua Yang; Jin Jing Li; Ying Chen; Dong Mei Cui; Chen Zhang

doi:10.14233/ajchem.2015.17551

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Issue Published : February 20, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Copper Catalyzed Synthesis of Aryl Azides from Aryl Bromides and Sodium Azide

https://doi.org/10.14233/ajchem.2015.17551

Ming Zeng

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China

Yu Hua Yang

Shanghai Mu Sen Pharmaceutical Technology Co., Ltd., Shanghai 200030 P.R. China

Jin Jing Li

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China

Ying Chen

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China

Dong Mei Cui

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China

Chen Zhang

School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P.R. China

Corresponding Author(s) : Dong Mei Cui

cuidongmei@zjut.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 5 (2015): Vol 27 Issue 5
Article Published : February 20, 2015

Abstract

Aryl azides were synthesized using heterogeneous porous Cu catalyst via a coupling reaction of aryl bromides with sodium azide under mild conditions. The catalyst can be recycled in five times without significant loss of their catalytic activity.

Keywords

Porous copper Aryl bromides Sodium azide Aryl azides

Zeng, M., Hua Yang, Y., Jing Li, J., Chen, Y., Mei Cui, D., & Zhang, C. (2015). Copper Catalyzed Synthesis of Aryl Azides from Aryl Bromides and Sodium Azide. Asian Journal of Chemistry, 27(5), 1698–1700. https://doi.org/10.14233/ajchem.2015.17551

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References

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S.D. Brown, T.A. Betley and J.C. Peters, J. Am. Chem. Soc., 125, 322 (2003); doi:10.1021/ja028448i.
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I. Salvatori, La Metallurgia Italiana, 98, 41 (2006).
T. Jin, M. Yan, Menggenbateer, T. Minato, M. Bao and Y. Yamamoto, Adv. Synth. Catal., 353, 3095 (2011); doi:10.1002/adsc.201100760.
C. Zhang, B. Huang, Y. Chen and D.M. Cui, New J. Chem., 37, 2606 (2013); doi:10.1039/c3nj00468f.
L. Di Nunno and A. Scilimati, Tetrahedron, 42, 3913 (1986); doi:10.1016/S0040-4020(01)87546-3.
M. Hu, J. Li and S. Q. Yao, Org. Lett., 10, 5529 (2008); doi:10.1021/ol802286g.
J.T. Markiewicz, O. Wiest and P. Helquist, J. Org. Chem., 75, 4887 (2010); doi:10.1021/jo101002p.
N.T. Pokhodylo, V.S. Matiichuk and N.D. Obushak, Russ. J. Org. Chem., 46, 556 (2010); doi:10.1134/S1070428010040196.
F. Alonso, Y. Moglie, G. Radivoy and M. Yus, Eur. J. Org. Chem., 1875 (2010); doi:10.1002/ejoc.200901446.
N.E. Travia, Z.G. Xu, J.M. Keith, E.A. Ison, P.E. Fanwick, M.B. Hall and M.M. Abu-Omar, Inorg. Chem., 50, 10505 (2011); doi:10.1021/ic2017853.

References

E.F.V. Scriven and K. Turnbull, Chem. Rev., 88, 297 (1988); doi:10.1021/cr00084a001.

S.D. Brown, T.A. Betley and J.C. Peters, J. Am. Chem. Soc., 125, 322 (2003); doi:10.1021/ja028448i.

G. Molteni and A. Ponti, Chem. Eur. J., 9, 2770 (2003); doi:10.1002/chem.200204681.

M. Carmen Paredes, G. Gonzalez and M. Victoria Martín, Heterocycles, 52, 237 (2000); doi:10.3987/COM-99-S15.

H.M.S. Kumar, B.V.S. Reddy, S. Anjaneyulu and J.S. Yadav, Tetrahedron Lett., 40, 8305 (1999); doi:10.1016/S0040-4039(99)01771-2.

J.A.R. Rodrigues, R.A. Abramovitch, J.D.F. de Sousa and G.C. Leiva, J. Org. Chem., 69, 2920 (2004); doi:10.1021/jo030287t.

Q. Liu and Y. Tor, Org. Lett., 5, 2571 (2003); doi:10.1021/ol034919+.

W. Zhu and D.W. Ma, Chem. Commun., 888 (2004); doi:10.1039/b400878b.

J. Andersen, U. Madsen, F. Björkling and X.F. Liang, Synlett, 2209 (2005); doi:10.1055/s-2005-872248.

Y.M.Z. Ahmed, M.I. Riad, A.S. Sayed, M.K. Ahlam and M.E.H. Shalabi, Powder Technol., 175, 48 (2007); doi:10.1016/j.powtec.2007.01.027.

I. Salvatori, La Metallurgia Italiana, 98, 41 (2006).

T. Jin, M. Yan, Menggenbateer, T. Minato, M. Bao and Y. Yamamoto, Adv. Synth. Catal., 353, 3095 (2011); doi:10.1002/adsc.201100760.

C. Zhang, B. Huang, Y. Chen and D.M. Cui, New J. Chem., 37, 2606 (2013); doi:10.1039/c3nj00468f.

L. Di Nunno and A. Scilimati, Tetrahedron, 42, 3913 (1986); doi:10.1016/S0040-4020(01)87546-3.

M. Hu, J. Li and S. Q. Yao, Org. Lett., 10, 5529 (2008); doi:10.1021/ol802286g.

J.T. Markiewicz, O. Wiest and P. Helquist, J. Org. Chem., 75, 4887 (2010); doi:10.1021/jo101002p.

N.T. Pokhodylo, V.S. Matiichuk and N.D. Obushak, Russ. J. Org. Chem., 46, 556 (2010); doi:10.1134/S1070428010040196.

F. Alonso, Y. Moglie, G. Radivoy and M. Yus, Eur. J. Org. Chem., 1875 (2010); doi:10.1002/ejoc.200901446.

N.E. Travia, Z.G. Xu, J.M. Keith, E.A. Ison, P.E. Fanwick, M.B. Hall and M.M. Abu-Omar, Inorg. Chem., 50, 10505 (2011); doi:10.1021/ic2017853.

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Copper Catalyzed Synthesis of Aryl Azides from Aryl Bromides and Sodium Azide

Corresponding Author(s) : Dong Mei Cui

Abstract

Keywords

Full Article

Download Citation

References

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