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Molecules 2010, 15(11), 7732-7741; doi:10.3390/molecules15117732

Application of Phosphine-Phosphite Ligands in the Iridium Catalyzed Enantioselective Hydrogenation of 2-Methylquinoline

Instituto de Investigaciones Químicas, Consejo Superior de Investigaciones Científicas and Universidad de Sevilla, Avda. Américo Vespucio 49, 41092 Sevilla, Spain
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Received: 6 October 2010 / Revised: 26 October 2010 / Accepted: 28 October 2010 / Published: 29 October 2010
(This article belongs to the Special Issue Bifunctional Catalysis)
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Abstract

The hydrogenation of 2-methylquinoline with Ir catalysts based on chiral phosphine-phosphites has been investigated. It has been observed that the reaction is very sensitive to the nature of the ligand. Optimization of the catalyst, allowed by the highly modular structure of these phosphine-phosphites, has improved the enantioselectivity of the reaction up to 73% ee. The influence of additives in this reaction has also been investigated. Contrary to the beneficial influence observed in related catalytic systems, iodine has a deleterious effect in the present case. Otherwise, aryl phosphoric acids produce a positive impact on catalyst activity without a decrease on enantioselectivity.
Keywords: asymmetric hydrogenation; chiral ligands; phosphines; phosphites; iridium; quinolines asymmetric hydrogenation; chiral ligands; phosphines; phosphites; iridium; quinolines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Rubio, M.; Pizzano, A. Application of Phosphine-Phosphite Ligands in the Iridium Catalyzed Enantioselective Hydrogenation of 2-Methylquinoline. Molecules 2010, 15, 7732-7741.

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