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Nano SiO2-bonded Ru-TsDPEN for catalytic resolution of 1,2-propanediol by two transfer hydrogenation

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Abstract

A new strategy was introduced for the catalytic resolution of 1,2-propanediol involving the successive oxidative kinetic resolution and asymmetric hydrogenation by two hydrogen transfer reactions catalyzed by nano SiO2-bonded Ru-TsDPEN [TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylene diamine]-derived catalysts composed of two opposite configurations. The catalysts were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), Brunauer-Emmett-Teller (BET), Fourier-transform infrared spectroscopy (FT-IR), thermogravimetry-derivative thermogravimetry (TG-DTG) analysis, and inductively coupled plasma atomic emission spectrometry (ICP-AES). Results showed that Ru-TsDPEN derived catalysts were successfully grafted on the nano SiO2, affording high catalytic conversions of >99 and 99%, selectivities of 47 and 98% and maximum ee values of >99 and >99% in the two reactions, which were due to the nano SiO2 with Ru-TsDPEN in the reaction system with high dispersion. Additionally, the catalysts exhibited excellent durability and were filtered and reused at least five times without noticeable catalysts deactivations.

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References

  1. Gupta, P., Naidu, S.V., and Kumar, P., Tetrahedron Lett., 2004, vol. 45, pp. 849–851.

    Article  CAS  Google Scholar 

  2. Yoshikawa, N., Xu, F., Arredondo, J.D., and Itoh, T., Org. Process Res. Dev., 2011, vol. 15, pp. 824–830.

    Article  CAS  Google Scholar 

  3. Barral, K., Priet, S., Sire, J., Neyts, J., Balzarini, J., Canard, B., and Alvarez, K., J. Med. Chem., 2006, vol. 49, pp. 7799–7806.

    Article  CAS  Google Scholar 

  4. Dehury, S.K., Hariharakrishnan, V.S., Tetrahedron Lett., 2007, vol. 48, pp. 2493–2496.

    Article  CAS  Google Scholar 

  5. Bálint, J., Egri, G., Kolbert, A., Dianóczky, C., Fogassy, E., Novák, L., and Poppe, L., Tetrahedron: Asymmetry, 1999, vol. 10, pp. 4017–4028.

  6. Poppe, L., Novák, L., Kajtár-Peredy, M., and Szántay, C., Tetrahedron: Asymmetry, 1993, vol. 4, pp. 2211–2217.

    Google Scholar 

  7. Busygin, I., Taskinen, A., Nieminen, V., Toukoniitty, E., Stillger, T., Leino, R., and Murzin, D.Y., J. Am. Chem. Soc., 2009, vol. 131, pp. 4449–4462.

    Article  CAS  Google Scholar 

  8. Petursson, S. and Jonsdottir, S., Tetrahedron: Asymmetry, 2011, vol. 22, pp. 1809–1812.

    Article  CAS  Google Scholar 

  9. Edin, M., Martín-Matute, B., and Bäckvall, J-E., Tetrahedron: Asymmetry, 2006, vol. 17, pp. 708–715.

    Article  CAS  Google Scholar 

  10. Shuklov, I.A., Dubrovina, N.V., Schulze, J., Tietz, W., and Börner, A., Tetrahedron Lett., 2014, vol. 55, pp. 3495–3497.

    Article  CAS  Google Scholar 

  11. Montes, V., Checa, M., Marinas, A., Boutonnet, M., Marinas, J.M., Urbano, F.J., Järas, S., and Pinel, C., Catal. Today, 2014, vol. 223, pp. 129–137.

    Article  CAS  Google Scholar 

  12. Yue, C.J., Gu, L.P., Su, Y., and Zhu, S.P., Reac. Kinet. Mech. Cat., 2014, vol. 111, pp. 633–645.

    Article  CAS  Google Scholar 

  13. Jiménez-Morales, I., Vila, F., Mariscal, R., and Jiménez–López, A., Appl.Catal. B, 2012, vols. 117, vol. 118, pp. 253–259.

    Article  Google Scholar 

  14. Iwasaki, F., Maki, T., Nakashima, W., Onomura, O., and Matsumura, Y., Org.Lett., 1999, vol. 1, pp. 969–972.

    Google Scholar 

  15. Kadyrov, R., Koenigs, R.M., Brinkmann, C., Voigtlaender, D., and Rueping, M., Angew. Chem. Int. Ed., 2009, vol. 48, pp. 7556–7559.

    Article  CAS  Google Scholar 

  16. Xu, H., Meng, Q.H., and Zhang, Z.G., Chin. J. Chem., 2008, vol. 26, pp. 1656–1658.

    Article  CAS  Google Scholar 

  17. Ohkuma, T., Utsumi, N., Watanabe, M., Tsutsumi, K., Arai, N., and Murata, K., Org. Lett., 2007, vol. 9, pp. 2565–2567.

    Google Scholar 

  18. Ikariya, T. and Blacker, A.J., Acc.Chem.Res., 2007, vol. 40, pp. 1300–1308.

    Article  CAS  Google Scholar 

  19. Fujii, A., Hashiguchi, S., Uematsu, N., Ikariya, T.., and Noyori, R., J.Am.Chem.Soc., 1996, vol. 118, pp. 2521–2567.

    Article  CAS  Google Scholar 

  20. Faller, J.W. and Lavoie, A.R., Org. Lett., 2001, vol. 3, pp. 3703–3706.

    Article  CAS  Google Scholar 

  21. Patti, A. and Pedotti, S., Tetrahedron: Asymmetry, 2010, vol. 21, pp. 2631–2637.

    Article  CAS  Google Scholar 

  22. Shi, J., Li, X., Wang, Q.R., Zhang, Y.H, and Tang, Y., J. Catal., 2012, vol. 291, pp. 87–94.

    Article  CAS  Google Scholar 

  23. Sahoo, S., Kumar, P., Lefebvre, F., and Halligudi, S.B., Appl.Catal., A, 2009, vol. 354, pp. 17–25.

    Article  CAS  Google Scholar 

  24. Mihalcik, D.J., and Lin, W.B., Angew. Chem. Int. Ed., 2008, vol. 47, pp. 6229–6232.

    Article  CAS  Google Scholar 

  25. Im, J-S., Ahn, S-H., and Park, Y-H., Chem. Eng. J., 2013, vol. 234, pp. 49–56.

    Article  CAS  Google Scholar 

  26. Li, J., Zhang, Y.M., Han, D.F., Gao, Q., and Li, C., J. Mol. Catal. A, Chem., 2009, vol. 298, pp. 31–35.

    Article  CAS  Google Scholar 

  27. Liu, P.N., Gu, P.M., Wang, F., and Tu, Y.Q., Org. Lett., 2004, vol. 6, pp. 169–172.

    Google Scholar 

  28. Ikariya, T., Hashiguchi, S., Murata, K., and Noyori, R., Organic Syntheses, 2005, vol. 82, pp. 10–17.

    Article  CAS  Google Scholar 

  29. Mukharjee, B.B. and Barai, S.V., Construction and Building Materials, 2014, vol. 68, pp. 416–425.

    Article  Google Scholar 

  30. Liu, P.N., Gu, P.M., Deng, J.G., Tu, Y.Q., and Ma, Y.P., Eur. J. Org. Chem., 2005, vol. 15, pp. 3221–3227.

    Article  Google Scholar 

  31. Liu, R., Cheng, T.Y., Kong, L.Y., Chen, C., Liu, G.H., and Li, H.X., J. Catal., 2013, vol. 307, pp. 55–61.

    Article  CAS  Google Scholar 

  32. Caro, Y., Torrado, M., Masaguer, C.F., and Raviña, E., Tetrahedron: Asymmetry, 2003, vol. 14, pp. 3689–3696.

    Article  CAS  Google Scholar 

  33. Ros, A., Magriz, A., Dietrich, H., Lassaletta, J.M., and Fernandez, R., Tetrahedron, 2007, vol. 63, pp. 7532–7537.

    Article  CAS  Google Scholar 

  34. Zhang, J.N., Yang, X.R., Zhou, H., Li, Y.Y., Dong, Z.R., and Gao, J.X., Green Chem., 2012, vol. 14, pp. 1289–1292.

    Article  Google Scholar 

  35. Han, M.L., Hu, X.P., Huang, J.D., Chen, L.G., and Zheng, Z., Tetrahedron: Asymmetry, 2011, vol. 22, pp. 222–225.

    Article  CAS  Google Scholar 

  36. Koike, T., Murata, K., and Ikariya, T., Org.Lett. 2000, vol. 2, pp. 3833–3836.

    Google Scholar 

  37. Pecháek, J., Václavik, J., Prech, J., Šot, P., Janušcak, J., Vilhanova, B., Vavrik, J., Kuzma, M., and Kacer, P., Tetrahedron: Asymmetry, 2013, vol. 24, pp. 233–239.

    Article  Google Scholar 

  38. Comas-Vives, A., Ujaque, G., and Lledós, A., THEOCHEM 2009, vol. 903, pp. 123–132.

    Article  CAS  Google Scholar 

  39. Chelucci, G., Coord. Chem. Rev., 2013, vol. 257, pp. 1887–1932.

    Article  CAS  Google Scholar 

  40. Clavero, P., Grabulosa, A., Font-Bardia, M., Muller, G., J. Mol. Catal. A: Chem., 2014, vol. 391, pp. 183–190.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemical Engineering, School of Science, Changzhou Institute of Technology, Changzhou, 213022, China

    Chuan-Jun Yue, Li-Ping Gu, Ya-Feng Zhuang & Bao-Liang Liu

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  1. Chuan-Jun Yue
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  2. Li-Ping Gu
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  3. Ya-Feng Zhuang
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  4. Bao-Liang Liu
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Correspondence to Chuan-Jun Yue.

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Yue, CJ., Gu, LP., Zhuang, YF. et al. Nano SiO2-bonded Ru-TsDPEN for catalytic resolution of 1,2-propanediol by two transfer hydrogenation. Russ J Appl Chem 88, 1207–1218 (2015). https://doi.org/10.1134/S1070427215070162

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