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Novel and efficient method for esterification catalyzed by 1-glycyl-3-methyl imidazolium chloride-iron (III) complex

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Abstract

1-Glycyl-3-methyl imidazolium chloride-iron (III) complex [[Gmim]Cl–Fe(III)] was found to be a heterogeneous catalyst for an efficient and greener solvent free synthesis of esters by the condensation of carboxylic acids and alcohols with excellent yield at ambient temperature. This operation formulates very interesting, ecological perspective due to simple reaction condition, isolation, and purification of products. In addition, this method features reusability of catalyst, reduced waste, thus making new protocol more environmentally suitable whilst no catalyst leaching was observed.

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References

  1. C. Salome, H. Kohn, Tetrahedron 65, 456 (2009)

    Article  CAS  Google Scholar 

  2. L.A. Paquette, Encyclopedia of reagents for organic synthesis (John Wiley, Chichester, 1995)

    Google Scholar 

  3. H. Shi, W. Zhu, H. Li, H. Liu, M. Zhang, Y. Yan, Z. Wang, Catal Comm 11, 588 (2010)

    Article  CAS  Google Scholar 

  4. Z. Yingwei, L. Zhen, X. Chungu, Chin. J. Catal. 32, 440 (2011)

    Article  Google Scholar 

  5. N. Nowrouzi, A.M. Mehranpour, J.A. Rad, Tetrahedron 66, 9596 (2010)

    Article  CAS  Google Scholar 

  6. S. Sunitha, S. Kanjilal, P. Srinivasa Reddy, R.B.N. Prasad, Tetrahedron Lett. 48, 6962 (2007)

    Google Scholar 

  7. J.-E. Won, H.-K. Kim, J.-J. Kim, H.-S. Yim, M.-J. Kim, S.-B. Kang, H.-A. Chung, S.-G. Lee, Y.-J. Yoon, Tetrahedron 63, 12720 (2007)

    Article  CAS  Google Scholar 

  8. Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 343, 393 (2001)

    Article  CAS  Google Scholar 

  9. R. Sebest, I. Kmentov, S. Tom, Green Chem. 10, 484 (2008)

    Article  Google Scholar 

  10. W.S. Miao, T.H. Chan, Adv Synth Cat 348, 1711 (2006)

    Article  CAS  Google Scholar 

  11. M. Lombardo, F. Pasi, S. Easwar, C. Trombini, Adv. Synth. Cat. 349, 2061 (2007)

    Article  CAS  Google Scholar 

  12. L. Zhou, L. Wang, Chem. Lett. 36, 628 (2007)

    Article  CAS  Google Scholar 

  13. M. Lombardo, F. Pasi, S. Easwar, C. Trombini, Synlett 2471 (2008)

  14. M. Lombardo, S. Easwar, A. DeMarco, F. Pasi, C. Trombini, Org. Biomol. Chem. 6, 4224 (2008)

    Article  CAS  Google Scholar 

  15. Y. Yang, Y. Zhang, S. Hao, Q. Kan, Chem. Eng. J. 171, 1356 (2011)

    Article  CAS  Google Scholar 

  16. S. Rani, B.R. Bhat, Tetrahedron Lett. 51, 6403 (2010)

    Article  CAS  Google Scholar 

  17. S.A. Moyer, T.W. Funk, Tetrahedron Lett. 51, 5430 (2010)

    Article  CAS  Google Scholar 

  18. C.T. Yeung, K.C. Sham, W.S. Lee, W.T. Wong, W.Y. Wong, H.L. Kwong, Inorg. Chim. Act. 362, 3267 (2009)

    Article  CAS  Google Scholar 

  19. J. Jankowsk, J. Paradowsk, J. Mlynarski, Tetrahedron Lett. 47, 5281 (2006)

    Article  Google Scholar 

  20. G. Xie, T. Li, A. Zhang, Inorg. Chem. Comm. 13, 1199 (2010)

    Article  CAS  Google Scholar 

  21. T. Hatanaka, R. Miyake, Y. Ishida, H. Kawaguchi, J. Organomet. Chem. 696, 4046 (2011)

    Article  CAS  Google Scholar 

  22. L. Chang, D. Shang, J. Xin, X. Liu, X. Feng, Tetrahedron Lett. 49, 6663 (2008)

    Article  CAS  Google Scholar 

  23. M. Kawatsura, Y. Komatsu, M. Yamamoto, S. Hayase, T. Itoh, Tetrahedron Lett. 48, 6480 (2007)

    Article  CAS  Google Scholar 

  24. W. Miao, T. Chan, Acc. Chem. Res. 39, 897 (2006)

    Article  CAS  Google Scholar 

  25. T.J. Geldbach, P.J. Dyson, J. Am. Chem. Soc. 126, 8114 (2004)

    Article  CAS  Google Scholar 

  26. D.B. Zhao, Z. Fei, T.J. Geldbach, R. Scopelliti, P.J. Dyson, J. Am. Chem. Soc. 126, 15876 (2004)

    Article  CAS  Google Scholar 

  27. K. Yamaguchi, C. Yoshida, S. Uchida, N. Mizuno, J. Am. Chem. Soc. 127, 530 (2005)

    Article  CAS  Google Scholar 

  28. P. Karthikeyan, P.N. Muskawar, S.A. Aswar, P.R. Bhagat, S.K. Sythana, J. Mol. Catal. A Chem. 358, 112 (2012)

    Article  CAS  Google Scholar 

  29. M.S. Niasari, T. Khosousi, S. Hydarzadeh, J. Mol. Catal. A Chem. 235, 150 (2005)

    Article  Google Scholar 

  30. M. Lakshmi Kantam, V. Bhaskar, B.M. Choudary, Catalysis Lett. 78, 1 (2002)

    Article  Google Scholar 

  31. P. Karthikeyan, S.A. Aswar, P.N. Muskawar, S.K. Sythana, P.R. Bhagat, S. Senthil Kumar, P.S. Satvat, Arabian J. Chem. (2011). doi:10.1016/j.arabjc.2011.11.007

    Google Scholar 

  32. S.D. Yang, L.Y. Wu, Z.Y. Yan, Z.L. Pan, Y.M. Liang, J. Mol. Catal. A: Chem. 268, 107 (2007)

    Article  CAS  Google Scholar 

  33. X. Hu, J. Mao, Y. Sun, H. Chen, H. Li, Catal Comm. 10, 1908 (2009)

    Article  CAS  Google Scholar 

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Acknowledgments

We greatfully acknowledge the management of VIT University for providing required facilities and SAIF (IITM) for providing the spectral data.

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Correspondence to Pundlik Rambhau Bhagat.

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Karthikeyan, P., Bhagat, P.R., Kumar, S.S. et al. Novel and efficient method for esterification catalyzed by 1-glycyl-3-methyl imidazolium chloride-iron (III) complex. J IRAN CHEM SOC 9, 983–990 (2012). https://doi.org/10.1007/s13738-012-0116-1

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