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- Title
Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces.
- Authors
Swart, Marthinus R.; Twigge, Linette; Erasmus, Elizabeth; Marais, Charlene; Bezuidenhoudt, Barend C. B.
- Abstract
p-Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross-metathesis of acrylates with prop-1-en-1-ylbenzenes under conditions that only give the prop-1-en-1-ylbenzene self-metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI-TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p-cresol and the chloride ligands of GII. XPS furthermore confirmed p-cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p-cresol allows for more facile interaction between electron-deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.
- Subjects
ELECTRON-deficient compounds; METATHESIS reactions; ELECTRON density; BENZYLIDENE compounds; BINDING energy; NUCLEAR magnetic resonance spectroscopy; RUTHENIUM catalysts
- Publication
European Journal of Inorganic Chemistry, 2021, Vol 2021, Issue 18, p1752
- ISSN
1434-1948
- Publication type
Article
- DOI
10.1002/ejic.202100078