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Molecules 2014, 19(5), 5522-5537; doi:10.3390/molecules19055522
Article

Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst

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Received: 16 March 2014; in revised form: 22 April 2014 / Accepted: 24 April 2014 / Published: 29 April 2014
(This article belongs to the Special Issue Ruthenium Complex)
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Abstract: Hemilabile ligands can release a free coordination site “on demand” of an incoming nucleophilic substrate while occupying it otherwise. This is believed to increase the thermal stability and activity of catalytic systems and therefore prevent decomposition via free coordination sites. In this investigation chelating pyridinyl-alcoholato ligands were identified as possible hemilabile ligands for incorporation into the second generation Grubbs precatalyst. The O,N-alcoholato ligands with different steric bulk could be successfully incorporated into the precatalysts. The incorporation of the sterically hindered, hemilabile O,N-ligands improved the thermal stability, activity, selectivity and lifetime of these complexes towards the metathesis of 1-octene. A decrease in the activity of the second generation Grubbs precatalyst was additionally observed after incorporating a hemilabile O,N-ligand with two phenyl groups into the system, while increasing their lifetime.
Keywords: second generation grubbs precatalyst; pyridinyl-alcoholato ligand; 1-octene metathesis; lifetime second generation grubbs precatalyst; pyridinyl-alcoholato ligand; 1-octene metathesis; lifetime
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

du Toit, J.I.; Jordaan, M.; Huijsmans, C.A.A.; Jordaan, J.H.L.; van Sittert, C.G.C.E.; Vosloo, H.C.M. Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst. Molecules 2014, 19, 5522-5537.

AMA Style

du Toit JI, Jordaan M, Huijsmans CAA, Jordaan JHL, van Sittert CGCE, Vosloo HCM. Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst. Molecules. 2014; 19(5):5522-5537.

Chicago/Turabian Style

du Toit, Jean I.; Jordaan, Margaritha; Huijsmans, Carlijn A.A.; Jordaan, Johannes H.L.; van Sittert, Cornelia G.C.E.; Vosloo, Hermanus C.M. 2014. "Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst." Molecules 19, no. 5: 5522-5537.



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