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Issue 9, 2017
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A redox-switchable ring-closing metathesis catalyst

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Abstract

A Ru(II) complex ligated to a quinone-annulated N-heterocyclic carbene (NHC) was synthesized as a redox-active analogue of the Hoveyda–Grubbs II generation catalyst. The complex exhibited a single reversible reduction with a E1/2 of −0.63 V (vs. SCE), and was successfully reduced and then oxidized with high fidelity using chemical reagents. While the catalyst facilitated a range of ring-closing metathesis (RCM) reactions in its neutral state, its activity was inhibited upon the introduction of a suitable reducing reagent. A series of density functional theory calculations revealed that the differences in catalytic activity may be attributed to the stronger donating ability of the reduced NHC ligand which stabilized a ruthenacyclobutane intermediate and thus suppressed the rate-determining retro-[2 + 2] cycloaddition step of the underlying RCM mechanism.

Graphical abstract: A redox-switchable ring-closing metathesis catalyst

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Publication details

The article was received on 11 Jan 2017, accepted on 26 May 2017 and first published on 13 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QI00018A
Citation: Inorg. Chem. Front., 2017,4, 1525-1532
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    A redox-switchable ring-closing metathesis catalyst

    D. N. Lastovickova, A. J. Teator, H. Shao, P. Liu and C. W. Bielawski, Inorg. Chem. Front., 2017, 4, 1525
    DOI: 10.1039/C7QI00018A

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