Manganese catalysts with molecular recognition functionality for selective alkene epoxidation

F. Jonathan, Hull Effiette L.O. Sauer, Christopher D. Incarvito, J. W. Faller, Gary W. Brudvig, Robert H. Crabtree

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30 Citations (Scopus)

Abstract

Selective epoxidation of alkenes is possible with a new manganese porphyrin catalyst, C PMR, that uses hydrogen bonding between the carboxylic acid on the substrate molecule and a Kemp's triacid unit. For two out of three olefin substrates employed, molecular recognition prevents the unselective oxidation of C-H bonds, and directs oxidation to the olefin moiety, giving only epoxide products. Weak diastereoselectivity is observed in the epoxide products, suggesting that molecular recognition affects the orientation of the catalyst-bound substrate. The previously reported manganese terpyridine complex C TMR is shown to be a superior epoxidation catalyst to the porphyrin catalyst C PMR. Good conversion of 2-cyclopentene acetic acid (substrate S2) with C PMR is consistent with molecular modeling, which indicates a particularly good substrate/catalyst match. Evidence suggests that hydrogen bonding between the substrate and the catalyst is critical in this system.

Original languageEnglish
Pages (from-to)488-495
Number of pages8
JournalInorganic Chemistry
Volume48
Issue number2
DOIs
Publication statusPublished - Jan 19 2009

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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    Jonathan, F., Sauer, H. E. L. O., Incarvito, C. D., Faller, J. W., Brudvig, G. W., & Crabtree, R. H. (2009). Manganese catalysts with molecular recognition functionality for selective alkene epoxidation. Inorganic Chemistry, 48(2), 488-495. https://doi.org/10.1021/ic8013464