Preparation and characterization of optically active Schiff base-oxovanadium(IV) and -oxovanadium(V) complexes and catalytic properties of these complexes on asymmetric oxidation of sulfides into sulfoxides with organic hydroperoxides.

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概要

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• Oxovanadium(V) complexes, V<SUP>V</SUP>O (Schiff base)Y (Y=ClO<SUB>4</SUB>, Cl, NO<SUB>3</SUB>), with quadridentate Schiff base ligands derived from optically active 1,2-diamines and salicylaldehyde or its derivatives were prepared by oxidizing the corresponding V<SUP>IV</SUP>O (Schiff base) with Ce<SUP>IV</SUP> in acetonitrile followed by the addition of HY. The complexes were characterized by their <SUP>1</SUP>H NMR, IR, UV-Vis, and circular dichroism spectra, and electrochemistry. Reversible reduction potentials (V<SUP>5+</SUP>/V<SUP>4+</SUP>) obtained by cyclic voltammetry for a series of oxovanadium(V) complexes with Schiff base ligands derived from 5-substituted salicylaldehydes showed a linear dependence on the Hammett parameter. Both the vanadium(IV) and the vanadium(V) complexes catalyze asymmetric oxidation of sulfides into the corresponding sulfoxides with organic hydroperoxides. The oxovanadium(IV) complex catalysts gave much better asymmetric induction than the oxovanadium(V) complex catalysts and in most cases the enantiomeric excess (ee) ranged between 20 and 40%. In the reaction of V<SUP>IV</SUP>O (Schiff base) with an organic hydroperoxide the complex is finally converted into the oxovanadium(V) species, and a dark brown intermediate is suggested to be the catalytically active species.

著者

• Kojima Masaaki

  Department Of Chemistry Faculty Of Science Okayama University

• Fujita Junnosuke

  Department of Chemistry Faculty of Science Osaka University

• Nakajima Kiyohiko

  Coordination Chemistry Laboratories, Institute for Molecular Science

• Kojima Katsuhide

  Department of Chemistry, Faculty of Science, Nagoya University

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