Highly Selective Olefin Metathesis with CAAC-Containing Ruthenium Benzylidenes

Danielle Butilkov, Alexander Frenklah, Illya Rozenberg, Sebastian Kozuch, N. Gabriel Lemcoff

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Several olefin metathesis reactions are studied, namely, jojoba oil oligomerization, methyl oleate self-metathesis, ring-closing metathesis (RCM) to form a nitrogen heterocycle, and 1,5-hexadiene acyclic diene metathesis polymerization (ADMET). The catalyst containing the Bertrand-Grubbs cyclic alkyl amino carbene (CAAC) ligand showed high selectivity by diminishing isomerization reactions; this was especially clear at high temperatures where the more widely used nitrogen heterocyclic carbene (NHC)-based catalysts show side reactions. Experimental and computational studies determined that it is much more difficult to produce ruthenium hydrides with CAAC, a property that can explain the improved observed activity. This finding opens a pathway for the development of even more selective olefin metathesis catalysts for reactions that require harsh conditions.

Original languageEnglish
Pages (from-to)7634-7637
Number of pages4
JournalACS Catalysis
Volume7
Issue number11
DOIs
StatePublished - 3 Nov 2017

Keywords

  • CAAC ligand
  • double-bond isomerization
  • homogeneous catalysis
  • olefin metathesis
  • ruthenium

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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