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Issue 12, 2015
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Lanthanide derivatives comprising arylhydrazones of β-diketones: cooperative E/Z isomerization and catalytic activity in nitroaldol reaction

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Abstract

Two complexes [KLa(HL1)2{(CH3)2NCHO}2(H2O)3] (1) and [Sm(H2O)9](E-H2L2)3·2H2O (2) were synthesized by the reaction of lanthanum(III) and samarium(III) nitrates with potassium 3-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonate (KH2L1) and potassium (E,Z)-5-chloro-3-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)-2-hydroxybenzenesulfonate (KH2L2), respectively. Both complexes were fully characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy, ESI-MS and single-crystal X-ray diffraction. Cooperative E,ZE isomerization of KH2L2, induced by resonance assisted hydrogen bonding and ionic interactions, occurs upon the interaction with Sm(III). Catalytic activities of KH2L1,2 and their lanthanide derivatives were evaluated in the Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes. Good yields (up to 91%) and diastereoselectivities (syn/anti 3 : 1) were observed in the reactions catalyzed by 1 in water.

Graphical abstract: Lanthanide derivatives comprising arylhydrazones of β-diketones: cooperative E/Z isomerization and catalytic activity in nitroaldol reaction

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Publication details

The article was received on 10 Dec 2014, accepted on 22 Jan 2015 and first published on 27 Jan 2015


Article type: Paper
DOI: 10.1039/C4DT03788J
Citation: Dalton Trans., 2015,44, 5602-5610
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    Lanthanide derivatives comprising arylhydrazones of β-diketones: cooperative E/Z isomerization and catalytic activity in nitroaldol reaction

    K. T. Mahmudov, M. F. C. Guedes da Silva, M. Sutradhar, M. N. Kopylovich, F. E. Huseynov, N. T. Shamilov, A. A. Voronina, T. M. Buslaeva and A. J. L. Pombeiro, Dalton Trans., 2015, 44, 5602
    DOI: 10.1039/C4DT03788J

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