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Vol. 25 No. 2 (2013): Vol 25 Issue 2

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Copper(I)-Catalyzed N-Arylation of N1,N3-Dibenzylmalonamide and N1,N3-Dibutylmalonamide Followed by Cleavage of the Malonyl Group with Aryl Halides Under Ligand-Free Conditions

https://doi.org/10.14233/ajchem.2013.13614
W.J. Zheng
Zhejiang Provincial Key Laboratory of Biometrology and Inspection & Quarantine, College of Life Sciences, China Jiliang University, Zhejiang 310018, P.R. China
W.F. Xu
Zhejiang Provincial Key Laboratory of Biometrology and Inspection & Quarantine, College of Life Sciences, China Jiliang University, Zhejiang 310018, P.R. China
C.X. Shi
School of Environmental and Chemical Engineering, Shanghai University, 99 Shangda Road, BaoShan District 200444, Shanghai, P.R. China
F.B. Ren
Zhejiang Provincial Key Laboratory of Biometrology and Inspection & Quarantine, College of Life Sciences, China Jiliang University, Zhejiang 310018, P.R. China ; Zhejiang Apeloa Medical Technology Co. Ltd, Dongyang 322118, P.R. China
X.L. Lu
Zhejiang Provincial Key Laboratory of Biometrology and Inspection & Quarantine, College of Life Sciences, China Jiliang University, Zhejiang 310018, P.R. China
Y.F. Zhou
Zhejiang Provincial Key Laboratory of Biometrology and Inspection & Quarantine, College of Life Sciences, China Jiliang University, Zhejiang 310018, P.R. China ; Zhejiang Apeloa Medical Technology Co. Ltd, Dongyang 322118, P.R. China

Corresponding Author(s) : X.L. Lu

cjluyh@163.com

Asian Journal of Chemistry, Vol. 25 No. 2 (2013): Vol 25 Issue 2

Abstract

We primarily developed a practical and convenient protocol to synthesize of aromatic amines based on CuI-catalyzed N-arylation of N1,N3-dibenzylmalonamide and N1,N3-dibutylmalonamide followed by cleavage of the malonyl group with aryl halides under ligand-free conditions giving good yields.

Keywords

Cleavage Cross-coupling N1 ,N3 -Dibenzylmalonamide N 1 ,N3 -Ditutylmalonamide Copper
Zheng, W., Xu, W., Shi, C., Ren, F., Lu, X., & Zhou, Y. (2012). Copper(I)-Catalyzed N-Arylation of N1,N3-Dibenzylmalonamide and N1,N3-Dibutylmalonamide Followed by Cleavage of the Malonyl Group with Aryl Halides Under Ligand-Free Conditions. Asian Journal of Chemistry, 25(2), 1117–1122. https://doi.org/10.14233/ajchem.2013.13614
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References
  1. (a) I.P. Beletskaya and A.V. Heprakov, Coord, Chem. Rev., 248, 2337 (2004); (b) E.M. Beccalli, G. Broggini and G. Martinelli, Chem. Rev., 107, 5318 (2007); (c) J.P. Corbert and G. Mingnani, Chem. Rev., 106, 2651 (2006); (d) S.V. Ley and A.W. Thomas, Angew. Chem. Int. Ed., 42, 5400 (2003).
  2. B.P. Fors, N.R. Davis and S.L. Buchwald, J. Am. Chem. Soc., 131, 5766 (2009); (b) M. Islam, P. Mondal, K. Tuhina, A.S. Roy, S. Mondal and D. Hossain, J. Organomet. Chem., 695, 2284 (2010); (c) A. Komaromi and Z. Novak, Adv. Synth. Catal., 352, 1523 (2010); (d) Q.L. Shen and J.F. Hartwig, Org. Lett., 10, 4109 (2008); (e) B.P. Fors and S.L. Buchwald, J. Am. Chem. Soc., 132, 15914 (2010); (f) Q.L. Shen, T. Ogata and J.F. Hartwig, J. Am. Chem. Soc., 130, 6586 (2008); (g) L. Chen, G.-A. Yu and S.-H. Liu, J. Organomet. Chem., 695, 1768 (2010); (h) A.A. Trabanco, J.A. Vega and M.A. Frenandez, J. Org. Chem., 72, 8146 (2007).
  3. (a) R. Giri and J.F. Hartwig, J. Am. Chem. Soc., 132, 15860 (2010); (b) L. Rout, S. Jammi and T. Punniyamurthy, Org. Lett., 9, 3397 (2007); (c) Y.-B. Huang, C.-T. Yang, J. Yi, X.-J. Deng, Y. Fu and L. Liu, J. Org. Chem., 76, 800 (2011); (d) T. Kubo, C. Katoh, K. Yamada, K. Okano, H. Tokuyama and T. Fukuyama, Tetrahedron, 64, 11230 (2008); (e) V.H. Jadhav, D.K. Dumbre, V.B. Phapale, H.B. Borate and R.D. Wakharkar, Catal. Commun., 8, 65 (2007).
  4. K. Swapna, A.V. Kumar, V.P. Reddy and K.R. Rao, J. Org. Chem., 74, 7514 (2009).
  5. L. Rout, P. Saha, S. Jammi and T. Punniyamurthy, Adv. Synth. Catal., 350, 395 (2008).
  6. F.-F. Yong and Y.-C. Teo, Tetrahedron Lett., 51, 3910 (2010).
  7. M. Kosugi, M. Kameyama and T. Migita, Chem. Lett., 927 (1983).
  8. D.L. Guo, H. Huang, J.Y. Xu, H.L. Jiang and H. Liu, Org. Lett., 10, 4513 (2008).
  9. A. Correa, M. Carril and C. Bolm, Chem. Eur. J., 14, 10919 (2008).
  10. Y.-S. Feng, Q.-S. Man, P. Pan, Z.-Q. Pan and H.-J. Xu, Tetrahedron Lett., 50, 2585 (2009).
  11. J.C. Mao, Q.Q. Hua, J. Guo and D.Q. Shi, Catal. Commun., 10, 341 (2008).
  12. M.H. Yang and F. Liu, J. Org. Chem., 72, 8969 (2007).
  13. (a) R.A. Altman, K.W. Anderson and S.L. Buchwald, J. Org. Chem., 73, 5167 (2008); (b) X. Guo, H.H. Rao, H. Fu, Y.Y. Jiang and Y.F. Zhao, Adv. Synth. Catal., 348, 2197 (2006).
  14. D.S. Jiang, H. Fu, Y.Y. Jiang and Y.F. Zhao, J. Org. Chem., 72, 672 (2007).
  15. Z. Wang, H. Fu, Y.Y. Jiang and Y.F. Zhao, Synlett, 16, 2540 (2008).
  16. J.W. Xie, X.H. Zhu, M. Huang, F. Meng, W.W. Chen and Y.Q. Wan, Eur. J. Org. Chem., 3219 (2010).
  17. Z.Q. Wu, L. Zhou, Z.Q. Jiang, D. Wu, Z.K. Li and X.G. Zhou, Eur. J. Org. Chem., 4971 (2010).
  18. X.H. Zhu, L. Su, L.Y. Huang, G. Chen, J.L. Wang, H.C. Song and Y.Q. Wan, Eur. J. Org. Chem., 635 (2009).
  19. X.H. Zhu, Y. Ma, L. Su, H.C. Song, G. Chen, D.C. Liang and Y.Q. Wan, Synthesis, 3955 (2006).
  20. K. Swapna, S.N. Murthy and Y.V.D. Nageswar, Eur. J. Org. Chem., 6678 (2010).
  21. Y.F. Liu, Y.J. Bai, J. Zhang, Y.Y. Li, J.P. Jiao and X.L. Qi, Eur. J. Org. Chem., 6084 (2007).
  22. Q. Jiang, D.S. Jiang, Y.Y. Jiang, H. Fu and Y.F. Zhao, Synlett, 1836 (2007).
  23. Z. Hu, W. Ye, H.B. Zou and Y.P. Yu, Synth. Commun., 40, 222 (2010).
  24. D.P. Wang and K. Ding, Chem. Commun., 1891 (2009).
  25. (a) C.-T. Yang, Y. Fu, Y.-B. Huang, J. Yi, Q.-X. Guo and L. Liu, Angew. Chem. Int. Ed., 48, 7398 (2009); (b) D.L. Guo, H. Huang, Y. Zhou, J.Y. Xu, H.L. Jiang, K.X. Chen and H. Liu, Green. Chem., 12, 276 (2010); (c) D. Zhu, R.L. Wang, J.C. Mao, L. Xu, F. Wu and B.S. Wan, J. Mol. Catal. A, 256, 256 (2006); (d) H.-J. Xu, F.-Y. Zheng, Y.-F. Liang, Z.-Y. Cai, Y.-S. Feng and D.-Q. Che, Tetrahedron Lett., 51, 669 (2010); (e) N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor and B.M. Bhanage, Tetrahedron Lett., 48, 6573 (2007); (f) H. Huang, X.H. Yan, W.L. Zhu, H. Li, H.L. Jiang and K.X. Chen, J. Comb. Chem., 10, 617 (2008).
  26. A. Correa, M. Carril and C. Bolm, Chem. Eur. J., 14, 10919 (2008).
  27. J.-Y. Goujon and M. Shipman, Tetrahedron Lett., 43, 9573 (2001).
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