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Synthesis and Metal Complexes of Thiourea Ligands Containing Carbohydrate-Derived Substituents

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Rust,  Jörg
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Sternberg, M., Rust, J., Lehmann, C. W., & Mohr, F. (2013). Synthesis and Metal Complexes of Thiourea Ligands Containing Carbohydrate-Derived Substituents. Helvetica Chimica Acta, 96(2), 280-288. doi:10.1002/hlca.201200386.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-C935-3
Abstract
Two glucose-derived thiourea derivatives, 2a and 2b, were prepared by addition of the corresponding amino sugars to a solution of 4-nitrobenzoyl isothiocyanate (Scheme 1). The thioureas were isolated as colorless solids in good yields and were fully characterized by NMR spectroscopy, optical rotation, elemental analysis, and also by single-crystal X-ray diffraction. Attempts to obtain CuII and NiII bis(chelate) complexes with these thioureas failed. However, the C(1)-protected thiourea derivative 2a reacted with orthopalladated acetato-bridged dimers to afford the corresponding monomeric PdII complexes 3 and 4 (Scheme 2). In these compounds, the thiourea coordinates to the metal as monoanionic O,S chelate ligand, which was confirmed by X-ray crystallography.