Factors affecting the catalytic epoxidation of olefins by iron porphyrin complexes and H2O2 in protic solvents

Wonwoo Nam, So Young Oh, Ying Ji Sun, Jinheung Kim, Won Ki Kim, Seung K. Woo, Woonsup Shin

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

The catalytic epoxidation of cyclohexene by iron(III) porphyrin complexes and H2O2 has been investigated in alcohol solvents to understand factors affecting the catalyst activity in protic solvents. The yields of cyclohexene oxide and the FeIII/II reduction potentials of iron porphyrin complexes were significantly affected by the protic solvents, and there was a close correlation between the product yields and the reduction potentials of the iron porphyrin catalysts. The role of alcohol solvents was proposed to control the electronic nature of iron porphyrin complexes that determines the catalyst activity in the epoxidation of olefins by H 2O2. We have also demonstrated that an electron-deficient iron porphyrin complex can catalyze the epoxidation of olefins by H 2O2 under conditions of limiting substrate with high conversion efficiency in a solvent mixture of CH3OH and CH 2Cl2.

Original languageEnglish
Pages (from-to)7903-7906
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number20
DOIs
Publication statusPublished - 2003 Oct 3

ASJC Scopus subject areas

  • Organic Chemistry

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