Abstract
The reactions of hydrogen transfer from 2-propanol on acetophenone in the presence of the system [Rh(cod)Cl]2–L] (L is bisaldimine ligands based on (R,R)-1,2-cyclohexanediimine and pyridine-, quinoline-, and thiophenecarboxaldehyde) were studied. Rhodium(I) complexes with optically active ligand showed a high catalytic activity (up to 345 h–1) and moderate enantioselectivity [up to 55% ee of (R)-1-phenyethanol]. The structure of rhodium complex with N,N'-(1R,2R)-cyclohexane-1,2-diyl-bis[1-(pyridine-2-yl)methanimine] was determined on the basis of the data of 1H and 13C NMR spectroscopy and quantum chemical calculations.
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Botteghi, C., Chelucci, G., Chessa, G., Delogu, G., Gladiali, S., and Soccolini, F.J., J. Organomet. Chem., 1986, vol. 304, nos. 1–2, p. 217. doi 10.1016/S0022-328X(00)99687-6
Chelucci, G., Coord. Chem. Rev., 2013, vol. 257, nos. 11–12, p. 1887. doi 10.1016/j.ccr.2012.12.002
Paredes, P., Díez, J., and Gamasa, M.P., Organometallics, 2008, vol. 27, no. 11, p. 2597. doi 10.1021/om7011997
Gladiali, S., Chelucci, G., Soccolini, F., Delogu, G., and Chessa, G., J. Organomet. Chem., 1989, vol. 370, nos. 1–3, p. 285. doi 10.1016/0022-328X(89)87292-4
Zassinovich, G. and Mestroni, G., J. Mol. Cat., 1987, vol. 42, no. 1, p. 81. doi 10.1016/0304-5102(87)85041-1
Desimoni, G., Faita, G., and Jørgensen, K.A., Chem. Rev., 2011, vol. 111, no. 11, p. 284. doi 10.1021/cr100339a
Pavlov, V.A., Vinogradov, M.G., Starodubtseva, E.V., Chel’tsova, G.V., Ferapontov, V.A., Malyshev, O.R., and Heise, G.L., Russ. Chem. Bull., 2001, vol. 50, no. 4, p. 734. doi 10.1023/A:1011393702787
Maillard, D., Pozzi, G., Quici, S., and Sinou, D., Tetrahedron, 2002, vol. 58, no. 20, p. 3971. doi 10.1016/S0040-4020(02)00247-8
Touchard, F., Bernard, M., Fache, F., Delbecq, F., Guiral, V., Sautet, P., and Lemaire, M., J. Organomet. Chem., 1998, vol. 567, no. 1, p. 133. doi 10.1016/0022-328X(89)87292-4
Murata, K., Ikariya, T., and Noyori, R., J. Org. Chem., 1999, vol. 64, no. 7, p. 2186. doi 10.1021/jo990213a
Touchard, F., Bernard, M., Fache, F., and Lemaire, M., J. Mol. Catal. (A), 1999, vol. 140, no. 1, p. 1. doi 10.1016/S1381-1169(98)00212-X
Cross, W.B., Daly, C.G., Boutadla, Y., and Singh, K., Dalton Trans., 2011, vol. 40, no. 38, p. 9722. doi 10.1039/C1DT10753D
Roszkowski, P., Maurin, J.K., and Czarnocki, Z., Tetrahedron: Asym., 2013, vol. 24, no. 11, p. 643. doi 10.1016/S1381-1169(98)00212-X
Foubelo, F., Nájera, C., and Yus, M., Tetrahedron: Asym., 2015, vol. 26, nos. 15–16, p. 769. doi 10.1016/S1381-1169(98)00212-X
Wang, D. and Astruc, D., Chem. Rev., 2015, vol. 115, no. 13, p. 6621. doi 10.1021/acs.chemrev.5b00203
Ito, J.-I. and Nishiyama, H., Tetrahedron Lett., 2014, vol. 55, no. 20, p. 3133. doi 10.1021/acs.chemrev.5b00203.
Noyori, R. and Hashiguchi, S., Acc. Chem. Res., 1997, vol. 30, no. 2, p. 97. doi 10.1021/ar9502341
Fujii, A., Hashiguchi, S., Uematsu, N., Ikariya, T., and Noyori, R., J. Am. Chem. Soc., 1996, vol. 118, no. 18, p. 2521. doi 10.1021/ja954126l
Nindakova, L.O., Shainyan, B.A., Albanov, A.I., and Shmidt, F.K., Russ J. Org. Chem., 2003, vol. 39, no. 7, p. 926. doi 10.1023/B:RUJO.0000003180.30666.61
Himeda, Y., Onozawa-Komatsuzaki, N., Sugihara, H., Arakawa, H., and Kasuga, K., J. Mol. Catal. (A), 2003, vol. 195, nos. 1–2, p. 95. doi 10.1016/S1381-1169(02) 00576-9
Zassinovich, G., Bettella, R., Mestroni, G., Bresciani-Pahor, N., Geremia, S., and Randacco, L., J. Organomet. Chem., 1989, vol. 370, nos. 1–3, p. 187. doi 10.1016/0022-328X(89)87284-5
Gomez, M., Jansat, S., Muller, G., Bonnet, M.C., Breuzard, J.A.J., and Lemaire, M., J. Organomet. Chem., 2002, vol. 659, nos. 1–2, p. 186. doi 10.1016/S0022-328X(02)01767-9
Gladiali, S. and Alberico, E., Chem. Soc. Rev., 2006, vol. 35, no. 3, p. 226. doi 10.1039/B513396C
Kühl, O., Functionalised N-Heterocyclic Carbene Complexes, Chichester: Wiley, 2010. doi 10.1002/9780470685839.
Jiménez, M. V., Pérez-Torrente, J.J., Bartolomé, M.I., Gierz, V., Lahoz, F.J., and Oro, L.A., Organometallics, 2008, vol. 27, no. 2, p. 224. doi 10.1021/om700728a
Jiménez, M.V., Fernández-Tornos, J., Pérez-Torrente, J.J., Modrego, F.J., Winterle, S., Cunchillos, C., Lahoz, F.J., and Oro, L.A., Organometallics, 2011, vol. 30, no. 20, p. 5493. doi 10.1021/om200747k
Gao, J. and Martell, A.E., Org. Biomol. Chem., 2003, vol. 1, no. 15, p. 2801. doi 10.1039/B305582E
Mellah, M., Voituriez, A., and Schulz, E., Chem. Rev., 2007, vol. 107, no. 12, p. 5133. doi 10.1021/cr068440h
Jiménez, M.V., Pérez-Torrente, J.J., Bartolomé, M.I., Vispe, E., Lahoz, F.J., and Oro, L.A., Macromolecules, 2009, vol. 42, no. 21, p. 8146. doi 10.1021/ma901549g
Frauenlob, R., McCormack, M.M., Walsh, C.M., and Bergin, E., Org. Biomol. Chem., 2011, vol. 9, no. 20, p. 6934. doi 10.1039/C1OB06180A
Nindakova, L.O., Shainyan, B.A., and Albanov, A.I., Russ. Chem. Bull., 2001, vol. 50, no. 10, p. 1860. doi 10.1023/A:1014390314872
Granovsky, A.A., Firefly version 8, http://classic.chem.msu.su/gran/firefly/index.htmL
Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, no. 11, p. 1347. doi 10.1002/jcc.540141112
Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley Interscience Publication, 1972.
Liu, B., Zhang, M.-J., Cui, J., and Zhu, J., Acta Crystallogr. (E), 2006, vol. 62, no. 12, p. 5359. doi 10.1107/S1600536806043388
Brethon, A., Moreau, J.J.E., and Man, M.W.C., Tetrahedron: Asym., 2004, vol. 15, no. 3, p. 495. doi 10.1016/j.tetasy.2003.11.005
Abu-Surrah, A.S., Thewalt, U., and Rieger, B., J. Organomet. Chem., 1999, vol. 587, no. 1, p. 58. doi 10.1016/S0022-328X(99)00273-9
Fonseca, M.H., Eibler, E., Zabel, M., and König, B., Inorg. Chim. Acta, 2003, vol. 352, p. 136. doi 10.1016/S0020-1693(03)00131-2
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
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Original Russian Text © L.O. Nindakova, N.M. Badyrova, E.Kh. Sadykov, I.A. Ushakov, S.Ch. Vanzarakshaeva, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 11, pp. 1794–1803.
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Nindakova, L.O., Badyrova, N.M., Sadykov, E.K. et al. Rhodium(I) bisaldimine complexes in transfer hydrogenation. Russ J Gen Chem 87, 2537–2545 (2017). https://doi.org/10.1134/S1070363217110056
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DOI: https://doi.org/10.1134/S1070363217110056