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

Kuhn, Kevin M. and Bourg, Jean-Baptiste and Chung, Cheol K. and Virgil, Scott C. and Grubbs, Robert H. (2009) Effects of NHC-Backbone Substitution on Efficiency in Ruthenium-Based Olefin Metathesis. Journal of the American Chemical Society, 131 (14). pp. 5313-5320. ISSN 0002-7863. PMCID PMC2679506. https://resolver.caltech.edu/CaltechAUTHORS:20090828-132523283

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja900067cDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja900067cPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2679506/PubMed CentralArticle
ORCID:
AuthorORCID
Virgil, Scott C.0000-0001-8586-5641
Grubbs, Robert H.0000-0002-0057-7817
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.
Funders:
Funding AgencyGrant Number
Department of Energy (DOE)DE-FG02-08ER15933
NIH5RO1 GM31332
Gordon and Betty Moore FoundationUNSPECIFIED
Materia, Inc.UNSPECIFIED
Issue or Number:14
PubMed Central ID:PMC2679506
Record Number:CaltechAUTHORS:20090828-132523283
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20090828-132523283
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15417
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:09 Sep 2009 22:39
Last Modified:09 Mar 2020 13:19

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