Copper(II) arylhydrazone complexes as catalysts for C[sbnd]H activation in the Henry reaction in water

Three new water-soluble copper(II) complexes [Cu(HL)(H2O){(CH3)2NCHO}] (1), [Cu(H2L)2(im)4]·CH3OH (2) and [Cu(HL)(CH3OH)]2(μ2-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[sbnd]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. © 2016

Authors
Ma Z.1, 2 , Gurbanov A.V. 2, 3 , Maharramov A.M.3 , Guseinov F.I.4, 5 , Kopylovich M.N.2 , Zubkov F.I. 6 , Mahmudov K.T. 2, 3 , Pombeiro A.J.L.2
Journal
Journal of Molecular Catalysis A: Chemical
Publisher
Elsevier B.V.
Language
English
Pages
526-533
Status
Published
Link
External link
DOI
10.1016/J.MOLCATA.2016.05.030
Volume
426
Year
2017
Organizations
  • 1 School of Chemistry and Chemical Engineering, Guangxi UniversityGuangxi 530004, China
  • 2 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 3 Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Baku, AZ 1148, Azerbaijan
  • 4 Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, Moscow, 119992, Russian Federation
  • 5 National University of Science and Technology «MISIS», Moscow Leninsky prosp. 4, Moscow, 119049, Russian Federation
  • 6 Department of Organic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
Keywords
Arylhydrazone of acetoacetanilide; Copper(II) complexes; C−H activation; Henry reaction in aqueous medium
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