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. doi:10.1021/om7008028. 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.
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| 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). | ||||||||||||
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| Issue or Number: | 4 | ||||||||||||
| PubMed Central ID: | PMC2440574 | ||||||||||||
| DOI: | 10.1021/om7008028 | ||||||||||||
| 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: | INVALID USER | ||||||||||||
| Deposited On: | 11 Mar 2015 21:29 | ||||||||||||
| Last Modified: | 10 Nov 2021 20:49 |
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