Issue 12, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
10 Dec 2014
Accepted
22 Jan 2015
First published
27 Jan 2015

Dalton Trans., 2015,44, 5602-5610

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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