Bis-N-heterocyclic Carbene Aminopincer Ligands Enable High Activity in Ru-Catalyzed Ester Hydrogenation

Journal article (2015)

Authors

G.A. Filonenko Eindhoven University of Technology

Mae Joanne B. Aguila DSM

Erik N. Schulpen Eindhoven University of Technology

R. van Putten Eindhoven University of Technology

Jelena Wiecko Freie Universität Berlin

Christian Müller Freie Universität Berlin

Laurent Lefort DSM

Emiel J.M. Hensen Eindhoven University of Technology

E.A. Pidko Eindhoven University of Technology

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Published Date

2015

Language

English

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Abstract

Bis-N-heterocyclic carbene (NHC) aminopincer ligands were successfully applied for the first time in the catalytic hydrogenation of esters. We have isolated and characterized a well-defined catalyst precursor as a dimeric [Ru₂(L)₂Cl₃]PF₆ complex and studied its reactivity and catalytic performance. Remarkable initial activities up to 283 000 h^-1 were achieved in the hydrogenation of ethyl hexanoate at only 12.5 ppm Ru loading. A wide range of aliphatic and aromatic esters can be converted with this catalyst to corresponding alcohols in near quantitative yields. The described synthetic protocol makes use of air-stable reagents available in multigram quantities, rendering the bis-NHC ligands an attractive alternative to the conventional phosphine-based systems.