Issue 12, 2014

Isotopic probes for ruthenium-catalyzed olefin metathesis

Abstract

Routes are described to previously unreported first- and second-generation Grubbs metathesis catalysts bearing a 13C label at the key benzylidene or methylidene site. Improved syntheses of the 2H-labelled isotopologues are also presented. Labelling at the alkylidene position is important because it provides unique, direct information about changes at the active site of the catalyst, and the fate of the [Ru][double bond, length as m-dash]CHR ligand during catalyst deactivation. A case study demonstrates the power of 13C-labelling in tracking the methylidene moiety in amine-induced decomposition of the second-generation complex RuCl2(PCy3)(H2IMes)([double bond, length as m-dash]13CH2). Also reported is the solubility of ethylene in C6D6 and CD2Cl2, measured at 296 ± 1.5 K and 101.0 ± 0.8 kPa.

Graphical abstract: Isotopic probes for ruthenium-catalyzed olefin metathesis

Supplementary files

Article information

Article type
Paper
Submitted
29 aug 2014
Accepted
24 sep 2014
First published
24 sep 2014

Catal. Sci. Technol., 2014,4, 4210-4218

Author version available

Isotopic probes for ruthenium-catalyzed olefin metathesis

J. A. M. Lummiss, A. G. G. Botti and D. E. Fogg, Catal. Sci. Technol., 2014, 4, 4210 DOI: 10.1039/C4CY01118J

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