Facile regiospecific aromatic hydroxylation in palladium azopyridines and structural characterization of phenolato product

Pal, Chandan Kumar ; Chattopadhyay, Surajit ; Sinha, Chittaranjan ; Bandyopadhyay, Debkumar ; Chakravorty, Animesh (1994) Facile regiospecific aromatic hydroxylation in palladium azopyridines and structural characterization of phenolato product Polyhedron, 13 (6-7). pp. 999-1003. ISSN 0277-5387

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S02775...

Related URL: http://dx.doi.org/10.1016/S0277-5387(00)83022-3

Abstract

The reaction of Na2PdCl4 with 2-(arylazo)pyridines (A) in ethanol affords yellow complexes of composition [PdACl2] in which the PdCl2 fragment has acis configuration [v(PdCl): 350, 365 cm-1]. Upon treating [PdACl2] with dilute sodium hydroxide in air the pendent aryl group is selectively hydroxylated at theortho position, affording the phenolato complex [PdBCl] in high yields [B- is deprotonated 2-(2'-hydroxyarylazo)pyridine]. A possible reaction pathway is proposed by analogy with the hydroxylation of certain organic compounds by OH-/O2. The crystal and molecular structure of one [PdBCl] complex is reported. In the highly planar complex, the PdN(azo) length is significantly shorter than the PdN(pyridine) length. A single PdCl stretch at 365 cm-1 characterizes [PdBCl] which, unliked [PdACl2], has a structured intense absorption in the visible region near 670 nm.

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