Asymmetric transfer hydrogenation of ketones by N,N-containing quinazoline-based ruthenium(II) complexes

Küçüktürkmen, Çiğdem; Agac, Ahmet; Eren, Aysel; Karakaya, İdris; Aslantaş, Mehmet; Çelik, Ömer; Ulukanlı, Sabri; Karabuğa, Şemistan

doi:10.1016/j.catcom.2015.11.013

Cited by 7 publications

(3 citation statements)

References 34 publications

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“…These results agree with the work of Sortais and co-workers on the reduction of aryl-alkyl ketones, catalyzed by manganese complexes bearing chiral diamine ligands . The results are also comparable with data from a similar work based on ruthenium complexes with 10 mol % of a base refluxed in 2-propanol for 45–180 min from which conversions between 90 and 97% were reported . However, the least conversion of 17% recorded for 2-methyl-3-hexanone over 20 h (entry 12) is clearly due to steric hindrance by the neighboring flexible sp 3 carbons that limit accessibility and coordination to the CO bond.…”

Section: Cth Of Ketonessupporting

confidence: 91%

Transfer Hydrogenation of Ketones Catalyzed by Symmetric Imino-N-heterocyclic Carbene Co(III) Complexes

Abubakar

Bala

2020

ACS Omega

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The synthesis of new moisture-sensitive imine-functionalized N-heterocyclic carbene (NHC) precursor salts [1-(2-[(hydroxyl-benzylidene)-amino]-ethyl)-3-R-3H-imidazole-1-ium bromide; R = methyl (1a), ethyl (1b), and benzyl (1c)] is reported. Subsequent deprotonation of 1a–c and coordination of the in situ generated NHC ligands to CoBr2 led to the isolation of air-stable six-coordinate Co(III) complexes 2a–c, respectively. All the salts and complexes were fully characterized. Single-crystal X-ray analysis of 2a and 2c showed octahedral Co centers hexacoordinated to two NHC carbons, two imine nitrogen atoms, and two phenolate oxygens in the form [C^N^O(Co3+)C^N^O]. The complexes were used in the catalytic transfer hydrogenation (CTH) of a range of ketones in 2-propanol as the solvent and hydrogen donor. Based on a low catalyst concentration of 0.4 mol %, significant conversions in the range of 70–99% were recorded at high turnover frequencies up to 1635 h–1. A mechanism to account for the steps involved in the CTH of cyclohexanone by complex 2a is proposed and supported by data from cyclic voltammetry, low-resolution mass spectrometry, UV, and IR spectroscopic techniques.

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Section: Cth Of Ketonessupporting

confidence: 91%

Transfer Hydrogenation of Ketones Catalyzed by Symmetric Imino-N-heterocyclic Carbene Co(III) Complexes

Abubakar

Bala

2020

ACS Omega

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“…These complexes catalysed the ATH of aryl methyl ketones with good conversions and variable enantioselectivities (9-91% ee). 61 Moreover, Xing and co-workers disclosed recently Ru(diphosphane)(diamine) ATH catalysts that feature a single stereogenic element, by combining a simple and readily available amino-pyridine ligand (1-(pyridin-2-yl)methanamine) with an achiral diphosphine, 1,3-diphenylphosphinopropane. 62 The design of this inspiring catalytic system relied on the hypothesis that this combination would replicate the stereo induction of the recognized Noyori's catalyst.…”

Section: Diphosphine-diamine Ruthenium Catalystsmentioning

confidence: 99%

“…Ruthenium(diphosphine)(diamine) catalysts with minimal stereogenicity for the ATH of aryl ketones. 61,62 Aminoalcohol, diamine and diamide derived  6 -arene-ruthenium catalysts.…”

Section: Diphosphine-diamine Ruthenium Catalystsmentioning

confidence: 99%

Bifunctional Homogeneous Catalysts Based on Ruthenium, Rhodium and Iridium in Asymmetric Hydrogenation

Michon

Agbossou‐Niedercorn

2022

Series on Chemistry, Energy and the Environment

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A pH‐Responsive Soluble‐Polymer‐Based Homogeneous Ruthenium Catalyst for Highly Efficient Asymmetric Transfer Hydrogenation (ATH)

Xie

Wang

et al. 2016

ChemPlusChem

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A pH‐responsive polymer has been synthesized successfully by means of copolymerization of dimethyl aminopropyl acrylamide (DMAPA) and N‐p‐styrenesulfonyl‐1,2‐diphenylethylenediamine (V‐TsDPEN). The pH‐responsive polymer coordination ruthenium complex was thus prepared and employed as an efficient catalyst for the asymmetric transfer hydrogenation (ATH) of various ketones. The polymer catalyst exhibited an attractive pH‐induced phase‐separable behavior in water: it could be dissolved in water when the pH of the solution was lower than 6.5 at the beginning of the reaction, but was precipitated completely from water when the pH of the solution was above 8.5 after reaction. Additionally, the catalysts were highly efficient for the ATH of a wide range of substrates that bore different functional groups and could be recycled easily from the aqueous solution by means of self‐separation. They could be recycled eight times without significant changes in catalytic activity and enantioselectivity.

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Asymmetric transfer hydrogenation of ketones by N,N-containing quinazoline-based ruthenium(II) complexes

Cited by 7 publications

References 34 publications

Transfer Hydrogenation of Ketones Catalyzed by Symmetric Imino-N-heterocyclic Carbene Co(III) Complexes

Transfer Hydrogenation of Ketones Catalyzed by Symmetric Imino-N-heterocyclic Carbene Co(III) Complexes

Bifunctional Homogeneous Catalysts Based on Ruthenium, Rhodium and Iridium in Asymmetric Hydrogenation

A pH‐Responsive Soluble‐Polymer‐Based Homogeneous Ruthenium Catalyst for Highly Efficient Asymmetric Transfer Hydrogenation (ATH)

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