T. Darbre, C. Dubs, E. Rusanov
Dec 1, 2002
Citations
0
Influential Citations
24
Citations
Journal
European Journal of Inorganic Chemistry
Abstract
The ligands 2,6-bis{[(pyrid-2-ylmethyl)amino]methyl}pyridine with an N5 pattern and (6-{[(pyrid-2-ylmethyl)amino]methyl}pyrid-2-yl)methanol with an N3O pattern were synthesized. ZnII complexes of the two ligands could be obtained, and the single-crystal X-ray structure of (2,6-bis{[(pyrid-2-ylmethyl)amino]methyl}pyridine)zinc chloride showed Zn coordination to all five nitrogen atoms. The strong complexation of 2,6-bis{[(pyrid-2-ylmethyl)amino]methyl}pyridine and (6-{[(pyrid-2-ylmethyl)amino]methyl}pyrid-2-yl)methanol with ZnII were demonstrated by 1H NMR spectroscopic studies and electrospray mass spectrometry. The coupling of 2-hydroxyacetophenone and benzaldehyde was studied in the presence of the prepared Zn complexes, and it was shown that the coupling product was obtained at room temperature in up to 60% yield with 7.5 mol % of the zinc catalyst. The present complexes mimic the active site of the zinc-dependent class II aldolases, where ZnII is coordinated to three nitrogen atoms. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)