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

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

doi:10.1021/jacs.5b04237

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

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

93 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7620-7623
Journal	Journal of the American Chemical Society
Volume	137
Issue number	24
DOIs	https://doi.org/10.1021/jacs.5b04237
Publication status	Published - 2015
Externally published	Yes

Access to Document

10.1021/jacs.5b04237

Cite this

@article{62c4d44b7d4b4f57babda0021f2cb701,

title = "Bis-N-heterocyclic Carbene Aminopincer Ligands Enable High Activity in Ru-Catalyzed Ester Hydrogenation",

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.",

author = "Filonenko, {Georgy A.} and Aguila, {Mae Joanne B.} and Schulpen, {Erik N.} and {Van Putten}, Robbert and Jelena Wiecko and Christian M{\"u}ller and Laurent Lefort and Hensen, {Emiel J.M.} and Pidko, {Evgeny A.}",

year = "2015",

doi = "10.1021/jacs.5b04237",

language = "English",

volume = "137",

pages = "7620--7623",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society (ACS)",

number = "24",

}

TY - JOUR

T1 - Bis-N-heterocyclic Carbene Aminopincer Ligands Enable High Activity in Ru-Catalyzed Ester Hydrogenation

AU - Filonenko, Georgy A.

AU - Aguila, Mae Joanne B.

AU - Schulpen, Erik N.

AU - Van Putten, Robbert

AU - Wiecko, Jelena

AU - Müller, Christian

AU - Lefort, Laurent

AU - Hensen, Emiel J.M.

AU - Pidko, Evgeny A.

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84933045623&partnerID=8YFLogxK

U2 - 10.1021/jacs.5b04237

DO - 10.1021/jacs.5b04237

M3 - Article

AN - SCOPUS:84933045623

SN - 0002-7863

VL - 137

SP - 7620

EP - 7623

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 24

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this