Synthetic, spectral and catalytic activity studies of ruthenium bipyridine and terpyridine complexes: Implications in the mechanism of the ruthenium(pyridine-2,6-bisoxazoline)(pyridine-2,6-dicarboxylate)-catalyzed asymmetric epoxidation of olefins utilizing H2O2

Man Kin Tse, Haijun Jiao, Gopinathan Anilkumar, Bianca Bitterlich, Feyissa Gadissa Gelalcha, Matthias Beller

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Various Ru(L1)(L2) (1) complexes (L1 = 2,2′-bipyridines, 2,2′:6′,2″-terpyridines, 6-(4S)-4-phenyl-4,5-dihydro-oxazol-2-yl-2,2′-bipyridinyl or 2,2′-bipyridinyl-6-carboxylate; L2 = pyridine-2,6-dicarboxylate, pyridine-2-carboxylate or 2,2′-bipyridinyl-6-carboxylate) have been synthesized (or in situ generated) and tested on epoxidation of olefins utilizing 30% aqueous H2O2. The complexes containing pyridine-2,6-dicarboxylate show extraordinarily high catalytic activity. Based on the stereoselective performance of chiral ruthenium complexes containing non-racemic 2,2′-bipyridines including 6-[(4S)-4-phenyl-4,5-dihydro-oxazol-2-yl]-[2,2′]bipyridinyl new insights on the reaction intermediates and reaction pathway of the ruthenium-catalyzed enantioselective epoxidation are proposed. In addition, a simplified protocol for epoxidation of olefins using urea hydrogen peroxide complex as oxidizing agent has been developed.

Original languageEnglish
Pages (from-to)4419-4433
Number of pages15
JournalJournal of Organometallic Chemistry
Volume691
Issue number21
DOIs
StatePublished - 15 Oct 2006
Externally publishedYes

Keywords

  • Epoxidation
  • Homogeneous catalysis
  • Mechanism
  • Olefin
  • Ruthenium

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