Rhenium-Catalyzed Epoxide Deoxygenation: Scope and Limitations

Kevin P. Gable, Eric C. Brown

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

Transfer of oxygen atoms from epoxides to triphenylphosphine is efficiently catalyzed by Tp′ReO3 [Tp′ = hydrido-tris-(3,5-dimethylpyrazolyl)borate] in benzene at 75-105 °C. The reaction tolerates a wide variety of functional groups including ketones (conjugated or non-conjugated to the new double bond), esters, nitriles, ethers, silyl ethers and phthalimides. Relative rates vary with substitution pattern and electronics; in general, monosubstituted and 2,2-disubstituted epoxides react fastest, and cis-2,3-disubstituted systems react faster than trans. Electron-withdrawing substituents promote the reaction.

Original languageEnglish
Pages (from-to)2243-2245
Number of pages3
JournalSynlett
Issue number14
DOIs
StatePublished - 2003

Keywords

  • Epoxide deoxygenation
  • O-atom transfer
  • Rhenium catalysis

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