Copper(II) coordination polymers of arylhydrazone of 1H-indene-1,3(2H)-dione linked by 4,4′-bipyridineor hexamethylenetetramine: Evaluation of catalytic activity in Henry reaction

Gonçalo A.O. Tiago, Kamran T. Mahmudov, M. Fátima C. Guedes da Silva, Ana P.C. Ribeiro, Fatali E. Huseynov, Luís C. Branco, Armando J.L. Pombeiro

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The 1D and the 2D copper(II) coordination polymers [{Cu(κN,OO′-L)}2(μ-1κN:2κN′-bpy)2]n (1) and [{Cu(μ-1κN,OO′:2κO″-L)}2(μ-1κN:2κN′-hmt)]n (2), respectively, were synthesized from copper(II) nitrate and sodium 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene) hydrazinyl)benzenesulfonate (NaHL), in the presence of 4,4′-bipyridine (4,4′-bpy) (for 1) or hexamethylenetetramine (hmt) (for 2). 1 and 2 are water soluble and are characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. Depending on the neutral linkers, the dianionic ligand L2− displays tri- (in 1) or tetradentate (in 2) binding modes. The Cu2+ in 1 adopts a distorted N3O2 square-pyramid coordination environment, while in 2 it displays a distorted N2O3 trigonal bipyramid geometry. The catalytic activity of 1 and 2 was evaluated in the diastereoselective Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes, in water and in organic solvents. β-Hydroxy nitroalkanes were obtained in high yields (up to 92%), and moderate-to-good syn/anti diastereoselectivities (up to 79:21), in water at room temperature.

Original languageEnglish
Pages (from-to)33-39
Number of pages7
JournalPolyhedron
Volume133
DOIs
Publication statusPublished - 5 Sep 2017

Keywords

  • 4,4′-Bipyridine
  • Arylhydrazone of 1H-indene-1,3(2H)-dione
  • Copper(II) complexes
  • Henry reaction in water
  • Hexamethylenetetramine

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