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

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. © 2017 Elsevier Ltd

Authors
Tiago G.A.O.1 , Mahmudov K.T.1, 2 , Guedes Da Silva M.F.C. , Ribeiro A.P.C.1 , Huseynov F.E. 2, 3 , Branco L.C.4 , Pombeiro A.J.L.1
Journal
Publisher
Elsevier Ltd
Language
English
Pages
33-39
Status
Published
Volume
133
Year
2017
Organizations
  • 1 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 2 Department of Ecology and Soil Sciences, Baku State University, Z. Xalilov Str. 23, Baku, Az-1148, Azerbaijan
  • 3 Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya Str., Moscow, 117198, Russian Federation
  • 4 REQUINTE, Departamento de Química, Faculdade de Ciências e Tecnologias da Universidade Nova de Lisboa, Quinta da Torre, Caparica, 2829-516, Portugal
Keywords
4,4′-Bipyridine; Arylhydrazone of 1H-indene-1,3(2H)-dione; Copper(II) complexes; Henry reaction in water; Hexamethylenetetramine
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