502723-66-2Relevant articles and documents
Syntheses of zinc complexes with multidentate nitrogen ligands: New catalysts for aldol reactions
Darbre, Tamis,Dubs, Christian,Rusanov, Eduard,Stoeckli-Evans, Helen
, p. 3284 - 3291 (2002)
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.
