Catalytic olefin cyclopropanation using μ-oxo-bis[(salen)iron(III)] complexes

Smita K. Edulji, SonBinh Nguyen*

*Corresponding author for this work

Research output: Contribution to journalArticle

56 Scopus citations

Abstract

A series of μ-oxo - bis[(salen)iron(III)] complexes was prepared from the reaction of the corresponding salen ligands with FeCl 3·6H2O in the presence of NEt3, and characterized by elemental analysis, infrared spectroscopy, and mass spectrometry. These air-stable complexes catalyzed the cyclopropanation of olefins with ethyl diazoacetate in good yields. The catalytic activity of these μ-oxo dimers, in the cyclopropanation of styrene, was examined as a. function of the diamine backbone and the substituents in the 3,3′- and 5,5′-positions of the phenyl rings on the ligands. Solvent variation, catalyst loading, and styrene concentration were investigated to determine the optimal reaction conditions. The complex [Fe(3,3′,5,5′- tBu4salen)]2O (1d) was identified as the most efficient catalyst in the series, which successfully catalyzed the cyclopropanation not only of styrene but also of less reactive substrates such as α-methylstyrene, α-(trifluoromethyl)styrene, 1,1-diphenylethylene, methylenecyclohexane, and n-butyl vinyl ether and internal olefins such as trans- and cis-β-methylstyrene and ethylidenecyclohexane.

Original languageEnglish (US)
Pages (from-to)3374-3381
Number of pages8
JournalOrganometallics
Volume22
Issue number17
DOIs
StatePublished - Aug 18 2003

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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