Open AccessBis-N-heterocyclic Carbene Aminopincer Ligands Enable High Activity in Ru-Catalyzed Ester Hydrogenation
Author(s) -
Georgy A. Filonenko,
Mae Joanne B. Aguila,
Erik N. Schulpen,
Robbert van Putten,
Jelena Wiecko,
Christian Müller,
Laurent Lefort,
Emiel J. M. Hensen,
Evgeny A. Pidko
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b04237
Subject(s) - chemistry , carbene , catalysis , phosphine , reagent , reactivity (psychology) , organic chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
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.