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Water‐Soluble Cobalt(II) and Copper(II) Complexes of 3‐(5‐Chloro‐2‐hydroxy‐3‐sulfophenylhydrazo)pentane‐2,4‐dione as Building Blocks for 3D Supramolecular Networks and Catalysts for TEMPO‐Mediated Aerobic Oxidation of Benzylic Alcohols
Author(s) -
Kopylovich Maximilian N.,
Mahmudov Kamran T.,
Haukka Matti,
Figiel Paweł J.,
Mizar Archana,
da Silva José A. L.,
Pombeiro Armando J. L.
Publication year - 2011
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201100348
Subject(s) - chemistry , cobalt , catalysis , tautomer , supramolecular chemistry , pentane , aqueous solution , ligand (biochemistry) , copper , medicinal chemistry , derivative (finance) , chelation , diketone , coordination complex , polymer chemistry , metal , inorganic chemistry , organic chemistry , molecule , biochemistry , receptor , financial economics , economics
Abstract A new water‐soluble β‐diketone azo derivative ― 3‐(5‐chloro‐2‐hydroxy‐3‐sulfophenylhydrazo)pentane‐2,4‐dione(H 3 L, 1 ) ― was synthesized and found to be stable in DMSO solution and in the solid state in the hydrazo tautomeric form. Its water‐soluble complexes [Co(HL)(en)(H 2 O)] · 4H 2 O ( 3 ) and the zwitterionic [Cu(L)(Hen)(H 2 O)] ( 4 ), with buffering properties, were prepared by reaction of cobalt(II) and copper(II) nitrates with the ethylenediammonium (H 2 en) salt of 1 , (H 2 en)(HL) ( 2 ). In the formation of 3 and 4 , 1 is a chelating ligand, and a crucial synthetic and structural role is played by en, allowing the organization of water‐soluble assemblies and influencing the overall 3D supramolecular arrangement. Compound 3 is the first cobalt complex with an azo derivative of a β‐diketone. Complex 4 acts as catalyst precursor for the aerobic TEMPO‐mediated selective oxidation of benzylic alcohols to the corresponding aldehydes in aqueous media.