CaltechAUTHORS
Published June 8, 2011 | Version Supplemental Material + Accepted Version
Journal Article Open

Protonolysis of a Ruthenium–Carbene Bond and Applications in Olefin Metathesis

Creators

  • 1. ROR icon California Institute of Technology
  • 2. ROR icon University of California, Riverside

Abstract

The synthesis of a ruthenium complex containing an N-heterocylic carbene (NHC) and a mesoionic carbene (MIC) is described wherein addition of a Brønsted acid results in protonolysis of the Ru–MIC bond to generate an extremely active metathesis catalyst. Mechanistic studies implicated a rate-determining protonation step in the generation of the metathesis-active species. The activity of the NHC/MIC catalyst was found to exceed those of current commercial ruthenium catalysts.

Additional Information

© 2011 American Chemical Society. Received: April 4, 2011. Published: May 16, 2011. Lawrence Henling and Dr. Michael Day are acknowledged for X-ray crystallographic analysis. Prof. Dennis Dougherty and Dr. Jay Labinger are thanked for helpful discussions. We are grateful to Dr. Alexey Fedorov for assisting with mass spectrometry studies and instrumentation. Financial support by NDSEG (fellowship to B.K.K.), FQNRT (fellowship to J.B.), NIH (R01GM68825, 5R01GM031332), and NSF (CHE-1048404) is acknowledged. The instrumentation facilities where this work was carried out were supported by NSF CHE-063094 and NIH RR027690.

Attached Files

Accepted Version - nihms297164.pdf

Supplemental Material - ja203070r_si_001.pdf

Supplemental Material - ja203070r_si_002.cif

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ja203070r_si_001.pdf

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Additional details

Identifiers

PMCID
PMC3121189
Eprint ID
24233
Resolver ID
CaltechAUTHORS:20110628-084528883

Funding

National Defense Science and Engineering Graduate (NDSEG) Fellowship
Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT)
NIH
R01GM68825
NIH
5R01GM031332
NIH
RR027690
NSF
CHE-1048404
NSF
CHE-063094

Dates

Created
2011-06-28
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field