Journal of Molecular Catalysis A-Chemical, Vol.426, 526-533, 2017
Copper(II) arylhydrazone complexes as catalysts for C-H activation in the Henry reaction in water
Three new water-soluble copper(II) complexes [Cu(HL)(H2O){(CH3)(2)NCHO}] (1), [Cu(H2L)(2)(im)(4)]center dot CH3OH (2) and [Cu(HL)(CH3OH)](2)(mu(2)-py) (3) were synthesized from copper(II) nitrate and sodium (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzene-sulfonate (NaH2L), in the absence (for 1) and presence of imidazole (im) (for 2) or pyrazine (py) (for 3), and fully characterized. The complexes 1-3 have been tested as stereoselective C-H activating catalysts for the model nitroaldol (Henry) condensation of nitroethane with various aldehydes in water. 1 was the most active catalyst affording 64-87% yields with syn/anti diasteroselectivities up to 77:23. Crown Copyright (C) 2016 Published by Elsevier B.V. All rights reserved.
Keywords:Arylhydrazone of acetoacetanilide;Copper(II) complexes;Henry reaction in aqueous medium;C-H activation