Short communication1D Zn(II) coordination polymer of arylhydrazone of 5,5-dimethylcyclohexane-1,3-dione as a pre-catalyst for the Henry reaction

•Dicarboxylic-functionalized arylhydrazone of dimedone•1D Zn(II)-coordination polymer•Homogeneous pre-catalyst for the diastereoselective Henry reaction in water

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).

Graphical abstractDownload full-size image