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Hydrogenation of Ketones on Dispersed Chiral-Modified Palladium Nanoparticles

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Abstract

Hydrogenation of acetophenone and esters of ketoacids with molecular hydrogen in the presence of the Pd(acac)2–(–)-cinchonidine–H2 catalytic system has been studied. The dependence of the molar ratio of (–)-cinchonidine/Pd on size and shape of palladium nanoparticles, formed in the system, also on reaction rate and enantioselectivity has been established. The nature of the regularities observed for the Pd(acac)2–(–)-cinchonidine–H2 catalytic system was discussed.

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References

  1. Bukhtiyarov, V.I. and Slin’ko, M.G., Russ. Chem. Rev., 2001, vol. 70, no. 2, p. 147. doi 10.1070/RC2001v070n02ABEH000637

    Article  CAS  Google Scholar 

  2. Borah, B.J., Saikia, K., Saikia, P.P., Barua, N.Ch., and Dutta, D.K., Catalysis Today, 2012, vol. 198, no. 1, p. 174. doi 10.1016/j.cattod.2012.03.083

    Article  CAS  Google Scholar 

  3. Dinç, M., Metina Ö., and Özkar, S., Catalysis Today, 2012, vol. 183, no. 1, p. 10. doi 10.1016/j.cattod.2011.05.007

    Article  Google Scholar 

  4. Zhu, C., Zeng, J., Lu, P., Liu, J., Gu, Zh., and Xia, Y., Chem. Eur. J., 2013, vol. 19, no. 16, p. 5127. doi 10.1002/chem.201203787

    Article  CAS  Google Scholar 

  5. Zhang, H., Jin, M., Xiong, Y., Lim, B., and Xia, Y., Acc. Chem. Res., 2013, vol. 46, no. 8, p. 1783. doi 10.1021/ar300209w

    Article  CAS  Google Scholar 

  6. Ramsurn, H. and Gupta, R.B., in New and Future Developments in Catalysis. Catalysis by Nanoparticles, Suib, S.L., Ed., Amsterdam; Boston; Heidelberg: Elsevier, 2013, ch. 15, p. 347.

  7. Mallick, K., Witcomb, M., J., Dinsmore, A., and Scurrell, M.S., J. Mater. Sci., 2006, vol. 41, no. 6, p. 1733. doi 10.1007/s10853-006-3950-7

    Article  CAS  Google Scholar 

  8. Pushkarev, V.V., Zhu, Z., An, K., Hervier, A., and Somorjai, G.A., Top Catal., 2012, vol. 55, nos. 19–20, p. 1257. doi 10.1007/s11244-012-9915-y

    Article  CAS  Google Scholar 

  9. Roy, S. and Perics, M.A., Org. Biomol. Chem., 2009, vol. 7, no. 13, p. 2669. doi 10.1039/b903921j

    Article  CAS  Google Scholar 

  10. Barbaro, P., Santo, V.D., and Liguori, F., Dalton Trans., 2010, vol. 39, no. 36, p. 8391. doi 10.1039/c002051f

    Article  CAS  Google Scholar 

  11. Harris, K.D.M. and Thomas, J.M., ChemCatChem., 2009, vol. 1, no. 2, p. 223. doi 10.1002/cctc.200900181

    Article  CAS  Google Scholar 

  12. Wu, B. and Zheng, N., Nano Today, 2013, vol. 8, no. 2, p. 168. doi 10.1016/j.nantod.2013.02.006

    Article  Google Scholar 

  13. Watt, J., Cheong, S., and Tilley, R.D., Nano Today, 2013, vol. 8, no. 2, p. 198. doi 10.1016/j.nantod.2013.03.001

    Article  CAS  Google Scholar 

  14. Semagina, N., Renken, A., and Kiwi-Minsker, L., J. Phys. Chem. (C), 2007, vol. 111, no. 37, p. 13933. doi 10.1021/jp073944k

    Article  CAS  Google Scholar 

  15. Semagina, N., Renken, A., Laub, D., and Kiwi-Minsker, L., J. Catalysis, 2007, vol. 246, no. 2, p. 308. doi 10.1016/j.jcat.2006.12.011

    Article  CAS  Google Scholar 

  16. Yasukawa, T., Miyamura, H., and Kobayashi, S., ACS Catal., 2016, vol. 6, no. 11, p. 7979. doi 10.1021/acscatal.6b02446

    Article  CAS  Google Scholar 

  17. Yasukawa, T., Suzuki, A., Miyamura, H., Nishino, K., and Kobayashi, S., J. Am. Chem. Soc., 2015, vol. 137, no. 20, p. 6616. doi 10.1021/jacs.5b02213

    Article  CAS  Google Scholar 

  18. Bartók, M., Felföldi, K., Szöllösi, G., and Bartók, T., Catal. Lett., 1999, vol. 61, no. 1, p. 1. doi 10.1023/A:1019008519015

    Article  Google Scholar 

  19. Baiker, A., J. Mol. Cat. (A), 2000, vol. 163, nos. 1–2, p. 205. doi 10.1023/A:1019008519015

    Article  CAS  Google Scholar 

  20. Murzin, D.Yu. and Toukoniitty, E., React. Kinet. Catal. Lett., 2007, vol. 90, no. 1, p. 19. doi 10.1007/s11144-007-5004-9

    Article  CAS  Google Scholar 

  21. Szöllösi, G., Hermán, B., Fülöp, F., and Bartók, M., React. Kinet. Catal. Lett., 2006, vol. 88, no. 2, p. 391. doi 10.1007/s11144-006-0076-5

    Article  Google Scholar 

  22. Burgi, T. and Baiker, A., Acc. Chem. Res., 2004, vol. 37, no. 11, p. 909. doi 10.1021/ar040072l.

    Article  Google Scholar 

  23. Margitfalvi, J.L. and Tfirst, E., J. Mol. Cat. (A), 1999, vol. 139, no. 1, p. 81. doi 10.1016/S1381-1169(98) 00197-6

    Article  CAS  Google Scholar 

  24. Bartók, M., Balázsik, K., and Notheisz, F., React. Kinet. Catal. Lett., 2002, vol. 77, no. 2, p. 363. doi 10.1023/A:1020852405963

    Article  Google Scholar 

  25. Yasukawa, T., Suzuki, A., Miyamura, H., Nishino, K., and Kobayashi, S., J. Am. Chem. Soc., 2015, vol. 137, no. 20, p. 6616. doi 10.1021/jacs.5b02213

    Article  CAS  Google Scholar 

  26. Bonnemann, H. and Braun, G.A., Chem. Eur. J., 1997, vol. 3, no. 8, p. 1200. doi 10.1002/chem.19970030805

    Article  CAS  Google Scholar 

  27. Studer, M., Blaser, H.-U., and Exner, C., Adv. Synth. Catal., 2003, vol. 345, no. 1–2, p. 45. doi 10.1002/adsc.200390029

    Article  CAS  Google Scholar 

  28. Mink, L., Ma, Zh., Olsen, R.A., James, J.N., Sholl, D.S., Mueller, L.J., and Zaera, F., Top Catal., 2008, vol. 48, nos. 1–4, p. 120. doi 10.1007/s11244-008-9041-z

    Article  CAS  Google Scholar 

  29. Hisaki, I., Hiraishi, E., Sasaki, T., Orita, H., Tsuzuki, S., Tohnai, N., and Miyata, M., Chem. Asian J., 2012, vol. 7, no. 11, p. 2607. doi 10.1002/asia.201200566

    Article  CAS  Google Scholar 

  30. Kubota, J. and Zaera, F., J. Am. Chem. Soc., 2001, vol. 123, no. 44, p. 11115. doi 10.1021/ja016722n

    Article  CAS  Google Scholar 

  31. Mallat, T., Orglmeister, E., and Baiker, A., Chem. Rev., 2007, vol. 107, no. 11, p. 4863. doi 10.1021/cr0683663

    Article  CAS  Google Scholar 

  32. Huang, Y., Chen, J., Chen, H., Li, R., Li, Y., Min, L., and Li, X., J. Mol. Cat. (A), 2001, vol. 170, nos. 1–2, p. 143. doi 10.1016/S1381-1169(01)00053-X

    Article  CAS  Google Scholar 

  33. Collier, P.J., Hall, T.J., Iggo, J.A., Johnston, P., Slipszenko, J.A., Wells, P.B., and Whyman, R., Chem. Commun., 1998, no. 14, p. 1451. doi 10.1039/A803901A

    Article  Google Scholar 

  34. Zhang, J., Yan, X., and Liu, H., J. Mol. Cat. (A), 2001, vol. 176, nos. 1–2, p. 281. doi 10.1016/S1381-1169(01) 00268-0

    Article  CAS  Google Scholar 

  35. Vargas, A., Hoxha, F., Bonalumi, N., Mallat, T., and Baiker, A., J. Catal., 2006, vol. 240, no. 2, p. 203. doi 10.1016/j.jcat.2006.03.022

    Article  CAS  Google Scholar 

  36. Gniewek, A., Ziółkowski, J.J., Trzeciak, A.M., and Kępiński, L., J. Catal., 2006, vol. 239, no. 2, p. 272. doi 10.1016/j.jcat.2006.02.002

    Article  CAS  Google Scholar 

  37. Durand, J., Teuma, E., and Gómez, M., Eur. J. Inorg. Chem., 2008, p. 3577. doi 10.1002/ejic.200800569

    Google Scholar 

  38. Khimicheskaya entsiklopediya (Chemical Encyclopedia), Knunyants, I.L., Ed., Moscow: Bol’shaya Rossiiskaya Entsiklopediya, 1992, vol. 3, p. 440.

  39. Ivanovskii, A.L., Russ. Chem. Rev., 2009, vol. 78, no. 4, p. 303. doi 10.1070/RC2009v078n04ABEH004036

    Article  CAS  Google Scholar 

  40. Baiker, A., Catalysis Today, 2005, vol. 100, p. 159. doi 10.1016/j.cattod.2004.12.001

    Article  CAS  Google Scholar 

  41. Kraynov, A., Suchopar, A., and Richards, R., Catal. Lett., 2006, vol. 110, nos. 1–2, p. 91. doi 10.1007/s10562-006-0090-2

    Article  CAS  Google Scholar 

  42. USA Patent 3474464, 1969; Ross. Zh. Khim., 1970, 19N102P.

  43. Chambers, W.J., Brasen, W.R., and Hause, Ch.R., J. Am. Chem. Soc., 1957, vol. 79, no. 4, p. 879. doi 10.1021/ja01561a025

    Article  Google Scholar 

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Authors and Affiliations

  1. Irkutsk National Research Technical University, ul. Lermontova 83, Irkutsk, 664074, Russia

    L. O. Nindakova, V. O. Strakhov & S. S. Kolesnikov

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  1. L. O. Nindakova
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  2. V. O. Strakhov
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  3. S. S. Kolesnikov
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Correspondence to L. O. Nindakova.

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Original Russian Text © L.O. Nindakova, V.O. Strakhov, S.S. Kolesnikov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 2, pp. 219–227.

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Nindakova, L.O., Strakhov, V.O. & Kolesnikov, S.S. Hydrogenation of Ketones on Dispersed Chiral-Modified Palladium Nanoparticles. Russ J Gen Chem 88, 199–207 (2018). https://doi.org/10.1134/S1070363218020044

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  • DOI: https://doi.org/10.1134/S1070363218020044

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