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Highly Active Ruthenium Metathesis Catalysts Exhibiting Unprecedented Activity and Z‑Selectivity

Rosebrugh, Lauren E. and Herbert, Myles B. and Marx, Vanessa M. and Ketiz, Benjamin K. and Grubbs, Robert H. (2013) Highly Active Ruthenium Metathesis Catalysts Exhibiting Unprecedented Activity and Z‑Selectivity. Journal of the American Chemical Society, 135 (4). pp. 1276-1279. ISSN 0002-7863. PMCID PMC3561903. doi:10.1021/ja311916m. https://resolver.caltech.edu/CaltechAUTHORS:20130307-133635184

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Abstract

A novel chelated ruthenium-based metathesis catalyst bearing an N-2,6-diisopropylphenyl group is reported and displays near-perfect selectivity for the Z-olefin (>95%), as well as unparalleled TONs of up to 7400, in a variety of homodimerization and industrially relevant metathesis reactions. This derivative and other new catalytically active species were synthesized using an improved method employing sodium carboxylates to induce the salt metathesis and C–H activation of these chelated complexes. All of these new ruthenium-based catalysts are highly Z-selective in the homodimerization of terminal olefins.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja311916mDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja311916mPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3561903/PubMed CentralArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2013 American Chemical Society. Received: December 11, 2012; Published: January 14, 2013. Dr. David VanderVelde is thanked for assistance with NMR experimentation and analysis. This work was financially supported by the NIH (R01-GM031332), the NSF (CHE-1212767), and the NSERC of Canada (fellowship to V.M.M.). Instrumentation on which this work was carried out was supported by the NIH (NMR spectrometer, RR027690). Materia, Inc. is thanked for its donation of metathesis catalysts.
Funders:
Funding AgencyGrant Number
NIHR01-GM031332
NSFCHE-1212767
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
NIHRR027690
Issue or Number:4
PubMed Central ID:PMC3561903
DOI:10.1021/ja311916m
Record Number:CaltechAUTHORS:20130307-133635184
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130307-133635184
Official Citation:Highly Active Ruthenium Metathesis Catalysts Exhibiting Unprecedented Activity and Z-Selectivity Lauren E. Rosebrugh, Myles B. Herbert, Vanessa M. Marx, Benjamin K. Keitz, and Robert H. Grubbs Journal of the American Chemical Society 2013 135 (4), 1276-1279
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:37377
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:07 Mar 2013 23:46
Last Modified:09 Nov 2021 23:28

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