Abstract
Nickel nanoparticles on the BAU-A active carbon or NaX zeolite catalyze hydrogenation of imines and enamines in a flow reactor in a gas phase or in a gas–liquid–solid catalyst system. The process occurs at atmospheric pressure of hydrogen and gives secondary or tertiary amines in a high yield.
Similar content being viewed by others
References
Popov, Yu.V., Mokhov, V.M., Nebykov, D.N., Shcherbakova, K.V., and Dontsova, A.A., Russ. J. Gen. Chem., 2018, vol. 88, no. 1, p. 20. doi 10.1134/S1070363218010048
Tarasevich, V.A. and Kozlov, N.G., Russ. Chem. Rev., 1999, vol. 68, no. 1, p. 55. doi 10.1070/RC1999v068n01ABEH000389
Abdel-Magid, A.F., Carson, K.G., Harris, B.D., Maryanoff, C.A., and Shah, R.D., J. Org. Chem., 1996, vol. 61, p. 3849. doi 10.1021/jo960057x
Gavrilov, M.S., Shklyaev, V.S., and Aleksandrov, B.B., Chem. Heterocycl. Compd., 1987, vol. 23, no. 8, p. 871. doi 10.1007/BF00473462
Tararov, V.I., Kadyrov, R., Riermeier, T.H., Holz, J., and Borner, A., Tetrahedron Lett., 2000, vol. 41, no. 14, p. 2351. doi 10.1016/S0040-4039(00)00197-0
Tararov, V.I., Kadyrov, R., Riermeier, T.H., and Borner, A., Adv. Synth. Catal., 2002, vol. 344, no. 2, p. 200. doi 10.1002/1615-4169(200202)344
Horwell, D.C. and Timms, G.H., Synth. Commun., 1979, vol. 9, no. 3, p. 223. doi 10.1080/00397917908066700
Cohen, J.H., Abdel-Magid, A.F., Almond, H.R., and Maryanoff, C.A., Tetrahedron Lett., 2002, vol. 43, no. 11, p. 1977. doi 10.1016/S0040-4039(02)00172-7
Mokhov, V.M., Popov, Yu.V., and Nebykov, D.N., Russ. J. Gen. Chem., 2014, vol. 84, no. 11, P., 2073. doi 10.1134/S1070363214110036
Korton, D.G., Haury, V.E., Davis, F.C., Mitchell, L.J., and Ballard, S.A., J. Org. Chem., 1954, vol. 19, no. 7, p. 1054. doi 10.1021/jo01372a010
Nilsson, A. and Carlson, R., Acta Chim. Scand. (B), 1985, vol. 39, no. 3, p. 187. doi 10.3891/acta.chem.scand.39b-0187
Imamoto, T., Iwadate, N., and Yoshida, K., Org. Lett., 2006, vol. 8, no. 11, p. 2289. doi 10.1021/ol060546b
Abdur-Rashid, K., Lough, A.J., and Morris, R.H., Organometallics, 2001, vol. 20, p. 1047. doi 10.1021/om001054k
Pickard, P.L. and Jenkins, S.H., J. Am. Chem. Soc., 1953, vol. 75, no. 23, p. 5899. doi 10.1021/ja01119a035
Xie, J.-H., Zhu Sh.-F., and Zhou, Q.-L., Chem. Rev., 2011, vol. 111, p. 1713. doi 10.1021/cr100218m
Willoughby, C.A., Buchwald, S.L., J. Am. Chem. Soc., 1992, vol. 114, p. 7562. doi 10.1021/ja00045a038
Burling, S., Whittlesey, M.K., and Williams, J.M.J., Adv. Synth. Catal., 2005, vol. 347, p. 591. doi.1002/adsc.200600638
Alonso, F., Riente, P., and Yus, M., Synlett., 2008, no. 9, p. 1289. doi 10.1055/s-2008-1072748
Alonso, F. and Yus, M., Chem. Soc. Rev., 2004, vol. 33, p. 284. doi 10.1039/B315131J
Mokhov, V.M. and Popov, Yu.V., Russ. J. Gen. Chem., 2014, vol. 84, no. 10, p. 1921. doi 10.1134/S1070363214100090
Popov, Yu.V., Mokhov, V.M., Latyshova, S.E., Nebykov, D.N., Panov, A.O., and Pletneva, M.Yu., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2276. doi 10.1134/S107036321710005X
Rahimizadeh, M., Bakhtiarpoor, Z., Eshghi, H., Pordel, M., and Rajabzadeh, G., Monatsh. Chem., 2009, vol. 140, no. 12, p. 1465. doi 10.1007/s00706-009-0205-8
Choudary, B.M., Ranganath, K.V.S., Yadav, J., and Kantam, M.L., Tetrahedron Lett., 2005, vol. 46, no. 8, p. 1369. doi 10.1016/j.tetlet.2004.12.078
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.V. Popov, V.M. Mokhov, S.E. Latyshova, D.N. Nebykov, A.O. Panov, T.M. Davydova, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 10, pp. 1585–1589.
For communication XIX, see [1].
Rights and permissions
About this article
Cite this article
Popov, Y.V., Mokhov, V.M., Latyshova, S.E. et al. Colloidal and Nanosized Catalysts in Organic Synthesis: XX. Continuous Hydrogenation of Imines and Enamines Catalyzed by Nickel Nanoparticles. Russ J Gen Chem 88, 2035–2038 (2018). https://doi.org/10.1134/S1070363218100018
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363218100018