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Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis

Marx, Vanessa M. and Sullivan, Alexandra H. and Melaimi, Mohand and Virgil, Scott C. and Keitz, Benjamin K. and Weinberger, David S. and Bertrand, Guy and Grubbs, Robert H. (2015) Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis. Angewandte Chemie International Edition, 54 (6). pp. 1919-1923. ISSN 1433-7851. PMCID PMC4713124. https://resolver.caltech.edu/CaltechAUTHORS:20141222-082728332

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Abstract

An expanded family of ruthenium-based metathesis catalysts bearing cyclic alkyl amino carbene (CAAC) ligands was prepared. These catalysts exhibited exceptional activity in the ethenolysis of the seed-oil derivative methyl oleate. In many cases, catalyst turnover numbers (TONs) of more than 100 000 were achieved, at a catalyst loading of only 3 ppm. Remarkably, the most active catalyst system was able to achieve a TON of 340 000, at a catalyst loading of only 1 ppm. This is the first time a series of metathesis catalysts has exhibited such high performance in cross-metathesis reactions employing ethylene gas, with activities sufficient to render ethenolysis applicable to the industrial-scale production of linear α-olefins (LAOs) and other terminal-olefin products.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201410797DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201410797/abstractPublisherArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201410797/suppinfoPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4713124/PubMed CentralArticle
ORCID:
AuthorORCID
Virgil, Scott C.0000-0001-8586-5641
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: November 5, 2014. Article first published online: 17 DEC 2014. Lawrence M. Henling is acknowledged for X-ray crystallography analysis. Dr. David VanderVelde is thanked for assistance with NMR experiments. Thay Ung, Dr. Daryl P. Allen, and Dr. Richard L. Pederson (Materia Inc.) are thanked for helpful discussions regarding initial experimentation and setup. This work was financially supported by the NIH (5R01GM031332, 7R01GM068825), the NSF (CHE-1212767), the DOE (DE-FG02-13ER16370), and NSERC (fellowship to VMM).
Funders:
Funding AgencyGrant Number
NIH5R01GM031332
NIH7R01GM068825
NSFCHE-1212767
Department of Energy (DOE)DE-FG02-13ER16370
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Issue or Number:6
PubMed Central ID:PMC4713124
Record Number:CaltechAUTHORS:20141222-082728332
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141222-082728332
Official Citation:Marx, V. M., Sullivan, A. H., Melaimi, M., Virgil, S. C., Keitz, B. K., Weinberger, D. S., Bertrand, G. and Grubbs, R. H. (2015), Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis. Angew. Chem. Int. Ed., 54: 1919–1923. doi: 10.1002/anie.201410797
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53064
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:22 Dec 2014 16:43
Last Modified:09 Mar 2020 13:19

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