1D Zn(II) coordination polymer of arylhydrazone of 5,5-dimethylcyclohexane-1,3-dione as a pre-catalyst for the Henry reaction

• Published in: Catalysis communications Vol. 87; pp. 49 - 52
• Main Authors: Martins, Nuno M.R., Mahmudov, Kamran T., da Silva, M. Fátima C. Guedes, Martins, Luísa M.D.R.S., Guseinov, Firudin I., Pombeiro, Armando J.L.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.12.2016
• Subjects: Arylhydrazone of 5,5-dimethylcyclohexane-1,3-dione; Catalytic activity; Henry reaction; Zinc(II) coordination polymer; Zinc(II) coordination polymer; Catalytic activity; Arylhydrazone of 5,5-dimethylcyclohexane-1,3-dione; Henry reaction
• ISSN: 1566-7367; 1873-3905
• DOI: 10.1016/j.catcom.2016.08.039

Reaction of a new hydrazone of β-diketone, 5-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)isophthalic acid (H3L), with zinc(II) nitrate hexahydrate in a mixture of DMF and water (1:1) under hydrothermal conditions affords the 1D coordination polymer [Zn(μ3-HL)(H2O)2]n∙nH2O (1), where one of the carboxylic groups links two Zn(II) centers in a bridging bidentate (syn-syn-type) mode and the remaining one ligates a third metal cation in a monodentate fashion. It was characterized by IR and NMR spectroscopies, ESI-MS, elemental and single-crystal X-ray crystal structural analyses. 1 acts as an efficient pre-catalyst for the Henry reaction at 40°C in aqueous medium, providing β-nitroalcohols with good yields (67–86%) and diastereoselectivities (syn:anti 77:23–69:31). [Display omitted] •Dicarboxylic-functionalized arylhydrazone of dimedone•1D Zn(II)-coordination polymer•Homogeneous pre-catalyst for the diastereoselective Henry reaction in water