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Published April 15, 2009 | Accepted Version + Supplemental Material
Journal Article Open

Effects of NHC-Backbone Substitution on Efficiency in Ruthenium-Based Olefin Metathesis


series of ruthenium olefin metathesis catalysts bearing N-heterocyclic carbene (NHC) ligands with varying degrees of backbone and N-aryl substitution have been prepared. These complexes show greater resistance to decomposition through C−H activation of the N-aryl group, resulting in increased catalyst lifetimes. This work has utilized robotic technology to examine the activity and stability of each catalyst in metathesis, providing insights into the relationship between ligand architecture and enhanced efficiency. The development of this robotic methodology has also shown that, under optimized conditions, catalyst loadings as low as 25 ppm can lead to 100% conversion in the ring-closing metathesis of diethyl diallylmalonate.

Additional Information

© 2009 American Chemical Society. Received January 5, 2009; Publication Date (Web): March 24, 2009. We gratefully acknowledge financial support from the DOE (DE-FG02-08ER15933), the NIH (5RO1 GM31332), and the Gordon and Betty Moore Foundation. J.B.B. also thanks Materia, Inc. for financial support. We thank Larry M. Henling and Dr. Michael W. Day (California Institute of Technology) for X-ray crystallographic analysis and Materia, Inc. for a generous donation of ruthenium complexes, especially 2 and 3. Supporting Information: Detailed experimental procedures and characterization data. Crystallographic details for 17 and 20 are provided in CIF format. This material is available free of charge via the Internet at http://pubs.acs.org.

Attached Files

Accepted Version - nihms105170.pdf

Supplemental Material - Kuhnja900067c_si_001.pdf

Supplemental Material - Kuhnja900067c_si_002.cif


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