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

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

Journal Article (2015)

Author(s)

Georgy A. Filonenko (Eindhoven University of Technology)

Mae Joanne B. Aguila (DSM)

Erik N. Schulpen (Eindhoven University of Technology)

Robbert 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)

Evgeny A. Pidko (Eindhoven University of Technology)

DOI related publication

https://doi.org/10.1021/jacs.5b04237 Final published version

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More Info

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Publication Year

2015

Language

English

Issue number

24

Volume number

137

Pages (from-to)

7620-7623

Downloads counter

212

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.