Polymer-supported ruthenium porphyrins: Versatile and robust epoxidation catalysts with unusual selectivity

Xiao Qi Yu, Jie Sheng Huang, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

147 Citations (Scopus)

Abstract

Carbonyl ruthenium(II) 5,10,15-tris(4-R-phenyl)-20-(4- hydroxyphenyl)porphyrins (R = Cl, Me) covalently attached to Merrifield's peptide resin were prepared. The catalyst with R = Cl was found to efficiently catalyze Cl2pyNO epoxidation of a wide variety of alkenes, including aromatic and aliphatic terminal alkenes, cis- and trans-stilbene, cyclohexene and cyclooctene, α,β-unsaturated ketones, conjugated enyne, glycal, and protected α-amino alkene. Unusual selectivities were observed for the epoxidations of 1,5-cyclooctadiene, cis-1-phenyl-3-penten-1-yne (9), 3,4,6-tri-O-acetyl-D-glucal (11), and 2-(Boc-amino)-1-phenylbut-3-ene (13), which feature a complete bisepoxide selectivity (1,5-cyclooctadiene), unprecedentedly high cis:trans ratio (9), and complete diastereoselectivity (11 and 13). The new heterogenized metalloporphyrin epoxidation catalysts are of high stability and reusability.
Original languageEnglish
Pages (from-to)5337-5342
Number of pages6
JournalJournal of the American Chemical Society
Volume122
Issue number22
DOIs
Publication statusPublished - 7 Jun 2000
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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