Searching for the hidden hydrides: the competition between alkene isomerization and metathesis with Grubbs catalysts

Ian W. Ashworth, Ian H. Hillier, David J Nelson, Jonathan M Percy, Mark A. Vincent

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system.

Original languageEnglish
Pages (from-to)5673–5677
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2012
Issue number29
DOIs
Publication statusPublished - Oct 2012

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Keywords

  • ruthenium
  • metathesis
  • homogeneous catalysis
  • density functional calculations
  • kinetics

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