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Synthesis and catalytic activity of supported acenaphthoimidazolylidene N-heterocyclic carbene ruthenium complex for ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP)

Hlil, Antsar R. and Moncho, Salvador and Tuba, Robert and Elsaid, Khaled and Szarka, Györgyi and Brothers, Edward N. and Grubbs, Robert H. and Al-Hashimi, Mohammed and Bazzi, Hassan S. (2016) Synthesis and catalytic activity of supported acenaphthoimidazolylidene N-heterocyclic carbene ruthenium complex for ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP). Journal of Catalysis, 344 . pp. 100-107. ISSN 0021-9517. https://resolver.caltech.edu/CaltechAUTHORS:20170112-105925233

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Abstract

Ruthenium catalyzed ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP) reactions using a supported bis(arylimino)acenaphthene N-heterocyclic carbene (BIAN-NHC) complex have been reported. The BIAN-NHC Ru-complex exhibits excellent catalytic activity and tolerates a wide range of substrates at low catalyst loadings. DFT calculations were also carried out on some selected key intermediates in the reaction mechanism to study the effect of having the conjugated aromatic moiety (BIAN-NHC) in the backbone of the complex. The newly synthesized BIAN-NHC Ru-complex shows comparable catalytic activities to the commercially available second generation Ru catalyst HG2. The recycled complex was reused for up to eight reaction cycles for the RCM of N,N-diallyl tosylamine affording a high average isolated yield, with lower levels of Ru contamination in the final product.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.jcat.2016.08.019DOIArticle
http://www.sciencedirect.com/science/article/pii/S0021951716301579PublisherArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Al-Hashimi, Mohammed0000-0001-6015-2178
Bazzi, Hassan S.0000-0002-5702-0091
Additional Information:© 2016 Elsevier Inc. Received 12 July 2016, Revised 25 August 2016, Accepted 27 August 2016, Available online 1 October 2016. The authors gratefully acknowledge support of this work from the Qatar National Research Fund project number: NPRP X-095-1-024. We also acknowledge Prof. Ivan Bela for his generous support for analyzing the polymers using GPC in his laboratory. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
Qatar National Research FundNPRP X-095-1-024
Subject Keywords:Supported BIAN-NHC ruthenium complex; Ring closing metathesis; Ring opening metathesis polymerization; Catalysis; Acenaphthenequinone
Record Number:CaltechAUTHORS:20170112-105925233
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170112-105925233
Official Citation:Antsar R. Hlil, Salvador Moncho, Robert Tuba, Khaled Elsaid, Györgyi Szarka, Edward N. Brothers, Robert H. Grubbs, Mohammed Al-Hashimi, Hassan S. Bazzi, Synthesis and catalytic activity of supported acenaphthoimidazolylidene N-heterocyclic carbene ruthenium complex for ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP), Journal of Catalysis, Volume 344, December 2016, Pages 100-107, ISSN 0021-9517, http://dx.doi.org/10.1016/j.jcat.2016.08.019. (http://www.sciencedirect.com/science/article/pii/S0021951716301579)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:73467
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:20 Jan 2017 00:35
Last Modified:03 Oct 2019 16:28

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