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Faster initiating olefin metathesis catalysts from introducing double bonds into cyclopropyl, cyclobutyl and cyclopentyl derivatives of Hoveyda-Grubbs precatalysts

Trzaskowski, B. and Goddard, W. A. and Grela, K. (2017) Faster initiating olefin metathesis catalysts from introducing double bonds into cyclopropyl, cyclobutyl and cyclopentyl derivatives of Hoveyda-Grubbs precatalysts. Molecular Catalysis, 433 . pp. 313-320. ISSN 2468-8231. https://resolver.caltech.edu/CaltechAUTHORS:20170525-074754954

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Abstract

We have used the M06-D3 flavor of density functional theory (DFT) to investigate the structures and free energies of initiation for a series of Hoveyda-Grubbs-like complexes in which the isopropoxy part replaced by selected saturated or unsaturated derivatives of cyclopropane, cyclobutane and cyclopentane. We show that the introduction of the double bond into this part of the complex weakens the ruthenium-oxygen bond, creating a series of potential catalysts capable of fast initiation metathesis. The addition to the nitro group in the para position of the benzylidene part of the complex also creates a potentially highly efficient ruthenium catalyst. We demonstrate that the Gibbs free energy of activation correlates with various structural and computational parameters of the precatalyst, including the Ru-O bond strength and partial charges on selected atoms.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/j.mcat.2016.12.018DOIArticle
http://www.sciencedirect.com/science/article/pii/S1381116916305799PublisherArticle
ORCID:
AuthorORCID
Goddard, W. A.0000-0003-0097-5716
Additional Information:© 2017 Elsevier B.V. Received 7 September 2016, Revised 20 December 2016, Accepted 26 December 2016, Available online 1 April 2017.
Subject Keywords:DFT; Olefin metathesis; Ruthenium; Hoveyda-Grubbs catalyst; Double-bond
Record Number:CaltechAUTHORS:20170525-074754954
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170525-074754954
Official Citation:B. Trzaskowski, W.A. Goddard, K. Grela, Faster initiating olefin metathesis catalysts from introducing double bonds into cyclopropyl, cyclobutyl and cyclopentyl derivatives of Hoveyda-Grubbs precatalysts, Molecular Catalysis, Volume 433, May 2017, Pages 313-320, ISSN 2468-8231, https://doi.org/10.1016/j.mcat.2016.12.018. (http://www.sciencedirect.com/science/article/pii/S1381116916305799)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77746
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:25 May 2017 15:58
Last Modified:03 Oct 2019 18:01

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