Abstract
Modification of Leucart-Wallach reaction using catalytic amounts of copper colloid particles was developed. Reductive amination of a series of cyclic ketones proceeds at 100°C under a small excess of formamide or of alkyl(aryl)ammonium formate.
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Mokhov, V.M., Popov, Yu.V., and Nebykov, D.N., Russ. J. Gen. Chem., 2014, vol. 84, no. 9, p. 1656.
Bekker, H., Berger, B., and Domschke, G., Organicum, Oxford: Pergamob, 1973. Translated under the title Organikum, Moscow: Mir, 2008, p. 180.
Mizuta, T., Sakaguchi, S., and Ishii, Y., J. Org. Chem., 2005, vol. 70, p. 2195. DOI: 10.1021/jo481708.
Storer, R.I., Carrera, D.E., Ni, Y., and MacMillan, D.W.C., J. Am. Chem. Soc., 2006, vol. 128, no. 1, p. 84. DOI: 10.1021/ja057222n.
Kitamura, M., Lee, D., Hayashi, Sh., Tanaka, Sh., and Yoshimura, M., J. Org. Chem., 2002, vol. 67, p. 8685. DOI: 10.1021/jo02032701.
Frolog, Yu.G., Kurs kolloidnoi khimii. Poverkhnostnye yavleniya i dispersnye sistemy (Course of Colloid Chemistry. Surface Phenomena and Disperse Systems), Moscow: Khimiya, 1998.
Zhou, X., Huang, Y., Liu, Ch., Loao, J., Lu, T., and Xing, W., Chem. Sus. Chem., 2010, vol. 3, p. 1379. DOI: 10.1002/cssc.201000199.
Mori, K., Dojo, M., and Yamashita, H., ACS Catal., 2013, vol. 3, p. 1114. DOI: org/10.1021/cs4000148n.
Bi, Q.-Y, Du, X.-L, Liu, Y.-M, Cao, Y., He, H.-Y., and Fan, K.-N., J. Am Chem. Soc., 2012, vol. 134, p. 8926. DOI: org/10.1021/ja301696e.
Zhang, S., Metin, O., Su, D., and Sun, Sh., Angew Chem. Int. Ed., 2013, vol. 52, p. 1. DOI: 10.1002/anie.201300276.
Alfa Aesar. Research Chemicals, Metals and Materials, 2006–2007, p. 720.
Sasaki, T., Eguchi, Sh., and Katada, T., J. Org. Chem., 1974, vol. 39, p. 1239. DOI: 10.1021/jo00923a017.
Skoldinov, A.P., Vikhlyaev, Yu.I., Klimova, N.V., Shmar’yan, M.I., Ul’yanova, O.V., and Lavrova, L.N., USSR Authors Certificate no. 580864, 1974; Byull. Izobret., 1977, no. 43.
Reynolds, D.D. and Kenyon, W.O., J. Am. Chem. Soc., 1950, vol. 72, p. 1597. DOI: 10.1021/ja01160a046.
Storesund, H.J. and Whiting, C.M., J. Chem. Soc., Perkin Trans. 2, 1975, no. 13, p. 1452. DOI: 10.1039/P29750001452.
USSR Patent no. 653726, 1977; Byll. Izobret., 1993, no. 3.
US Patent no. 4223138, 1978.
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Original Russian Text © Yu.V. Popov, V.M. Mokhov, I.I. Budko, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 10, pp. 1636–1641.
For communication VI, see [1].
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Popov, Y.V., Mokhov, V.M. & Budko, I.I. Colloid and nanosize catalysts in organic synthesis: VII. Catalysis with copper colloid particles in Leucart-Wallach reaction. Russ J Gen Chem 84, 1915–1920 (2014). https://doi.org/10.1134/S1070363214100089
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DOI: https://doi.org/10.1134/S1070363214100089