Highly efficient abnormal NHC ruthenium catalyst for Oppenauer-type oxidation and transfer hydrogenation reactions

Lorenz Pardatscher; Benjamin J. Hofmann; Pauline J. Fischer; Sebastian M. Hölzl; Robert M. Reich; Fritz E. Kühn; Walter Baratta

doi:10.1021/acscatal.9b03677

Highly efficient abnormal NHC ruthenium catalyst for Oppenauer-type oxidation and transfer hydrogenation reactions

Lorenz Pardatscher, Benjamin J. Hofmann, Pauline J. Fischer, Sebastian M. Hölzl, Robert M. Reich, Fritz E. Kühn, Walter Baratta

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

35 Citations (Scopus)

Abstract

The ruthenium complex [Ru(OAc)(a-PC)2]Br (3) containing two abnormal NHC ligands is obtained by reaction of Ru(OAc)2(PPh3)2 (1) with 1-(2-diphenylphosphinoethyl)-3-mesitylimidazolium bromide in the presence of NaOAc. Complex 3 catalyzes the Oppenauer-type oxidation of a number of alcohols at unrivalled reaction rates reaching TOFs up to 550 000 h-1, at low catalyst loadings (S/C higher than 10 000) and using acetone in stoichiometric amounts. Complex 3 is also highly active in the reverse transfer hydrogenation of several ketones with 2-propanol, displaying TOFs up to 600 000 h-1.

Original language	English
Pages (from-to)	11302-11306
Number of pages	5
Journal	ACS Catalysis
Volume	9
Issue number	12
Early online date	4 Nov 2019
DOIs	https://doi.org/10.1021/acscatal.9b03677
Publication status	Published - 6 Dec 2019

Keywords

alcohols
carbonyl compounds
N-heterocyclic carbenes
Oppenauer-type oxidation
ruthenium
smart ligands
transfer hydrogenation

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10.1021/acscatal.9b03677

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title = "Highly efficient abnormal NHC ruthenium catalyst for Oppenauer-type oxidation and transfer hydrogenation reactions",

abstract = "The ruthenium complex [Ru(OAc)(a-PC)2]Br (3) containing two abnormal NHC ligands is obtained by reaction of Ru(OAc)2(PPh3)2 (1) with 1-(2-diphenylphosphinoethyl)-3-mesitylimidazolium bromide in the presence of NaOAc. Complex 3 catalyzes the Oppenauer-type oxidation of a number of alcohols at unrivalled reaction rates reaching TOFs up to 550 000 h-1, at low catalyst loadings (S/C higher than 10 000) and using acetone in stoichiometric amounts. Complex 3 is also highly active in the reverse transfer hydrogenation of several ketones with 2-propanol, displaying TOFs up to 600 000 h-1.",

keywords = "alcohols, carbonyl compounds, N-heterocyclic carbenes, Oppenauer-type oxidation, ruthenium, smart ligands, transfer hydrogenation",

author = "Lorenz Pardatscher and Hofmann, {Benjamin J.} and Fischer, {Pauline J.} and H{\"o}lzl, {Sebastian M.} and Reich, {Robert M.} and K{\"u}hn, {Fritz E.} and Walter Baratta",

year = "2019",

month = dec,

day = "6",

doi = "10.1021/acscatal.9b03677",

language = "English",

volume = "9",

pages = "11302--11306",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "12",

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Highly efficient abnormal NHC ruthenium catalyst for Oppenauer-type oxidation and transfer hydrogenation reactions. / Pardatscher, Lorenz; Hofmann, Benjamin J.; Fischer, Pauline J.; Hölzl, Sebastian M.; Reich, Robert M.; Kühn, Fritz E.; Baratta, Walter.

In: ACS Catalysis, Vol. 9, No. 12, 06.12.2019, p. 11302-11306.

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

TY - JOUR

T1 - Highly efficient abnormal NHC ruthenium catalyst for Oppenauer-type oxidation and transfer hydrogenation reactions

AU - Pardatscher, Lorenz

AU - Hofmann, Benjamin J.

AU - Fischer, Pauline J.

AU - Hölzl, Sebastian M.

AU - Reich, Robert M.

AU - Kühn, Fritz E.

AU - Baratta, Walter

PY - 2019/12/6

Y1 - 2019/12/6

N2 - The ruthenium complex [Ru(OAc)(a-PC)2]Br (3) containing two abnormal NHC ligands is obtained by reaction of Ru(OAc)2(PPh3)2 (1) with 1-(2-diphenylphosphinoethyl)-3-mesitylimidazolium bromide in the presence of NaOAc. Complex 3 catalyzes the Oppenauer-type oxidation of a number of alcohols at unrivalled reaction rates reaching TOFs up to 550 000 h-1, at low catalyst loadings (S/C higher than 10 000) and using acetone in stoichiometric amounts. Complex 3 is also highly active in the reverse transfer hydrogenation of several ketones with 2-propanol, displaying TOFs up to 600 000 h-1.

AB - The ruthenium complex [Ru(OAc)(a-PC)2]Br (3) containing two abnormal NHC ligands is obtained by reaction of Ru(OAc)2(PPh3)2 (1) with 1-(2-diphenylphosphinoethyl)-3-mesitylimidazolium bromide in the presence of NaOAc. Complex 3 catalyzes the Oppenauer-type oxidation of a number of alcohols at unrivalled reaction rates reaching TOFs up to 550 000 h-1, at low catalyst loadings (S/C higher than 10 000) and using acetone in stoichiometric amounts. Complex 3 is also highly active in the reverse transfer hydrogenation of several ketones with 2-propanol, displaying TOFs up to 600 000 h-1.

KW - alcohols

KW - carbonyl compounds

KW - N-heterocyclic carbenes

KW - Oppenauer-type oxidation

KW - ruthenium

KW - smart ligands

KW - transfer hydrogenation

UR - http://www.scopus.com/inward/record.url?scp=85075132640&partnerID=8YFLogxK

U2 - 10.1021/acscatal.9b03677

DO - 10.1021/acscatal.9b03677

M3 - Article

VL - 9

SP - 11302

EP - 11306

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 12

ER -

Highly efficient abnormal NHC ruthenium catalyst for Oppenauer-type oxidation and transfer hydrogenation reactions

Abstract

Keywords

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