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Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes

Anderson, Donde R. and Ung, Thay and Mkrtumyan, Garik and Bertrand, Guy and Grubbs, Robert H. and Schrodi, Yann (2008) Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes. Organometallics, 27 (4). pp. 563-566. ISSN 0276-7333. PMCID PMC2440574. https://resolver.caltech.edu/CaltechAUTHORS:20150311-104435790

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Abstract

The evaluation of ruthenium olefin metathesis catalysts 4–6 bearing cyclic (alkyl)(amino)carbenes (CAACs) in the cross-metathesis of cis-1,4-diacetoxy-2-butene (7) with allylbenzene (8) and the ethenolysis of methyl oleate (11) is reported. Relative to most NHC-substituted complexes, CAAC-substituted catalysts exhibit lower E/Z ratios (3:1 at 70% conversion) in the cross-metathesis of 7 and 8. Additionally, complexes 4–6 demonstrate good selectivity for the formation of terminal olefins versus internal olefins in the ethenolysis of 11. Indeed, complex 6 achieved 35 000 TONs, the highest recorded to date. CAAC-substituted complexes exhibit markedly different kinetic selectivity than most NHC-substituted complexes.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/om7008028DOIArticle
http://pubs.acs.org/doi/abs/10.1021/om7008028PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2440574/PubMed CentralArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2008 American Chemical Society. Received August 6, 2007. D.R.A. acknowledges NSF and NDSEG predoctoral fellowships. G.M., T.U., and Y.S. thank the DOE (DE-FG36-04GO14016) and Cargill, Inc. for financial support. R.H.G. is grateful to the NSF for funding (CHE-0410425). G.B. thanks the NIH for financial support (R01 GM 68825).
Funders:
Funding AgencyGrant Number
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Department of Energy (DOE)DE-FG36-04G014016
Cargill, Inc.UNSPECIFIED
NSFCHE-0410425
NIHR01 GM 68825
Issue or Number:4
PubMed Central ID:PMC2440574
Record Number:CaltechAUTHORS:20150311-104435790
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150311-104435790
Official Citation:Anderson, D. R., Ung, T., Mkrtumyan, G., Bertrand, G., Grubbs, R. H., & Schrodi, Y. (2008). Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes. Organometallics, 27(4), 563-566. doi: 10.1021/om7008028
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55700
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:11 Mar 2015 21:29
Last Modified:03 Oct 2019 08:07

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