ChemInform Abstract: Transfer Hydrogenation of Carbonyl Compounds and Alkenes Catalyzed by Ruthenium(II)—N-Heterocycle Carbene Complexes.

ChemInform ◽  
2008 ◽  
Vol 39 (1) ◽  
Author(s):  
Marianna Fekete ◽  
Ferenc Joo
Keyword(s):  
Carbonyl Compounds ◽  
Transfer Hydrogenation ◽  
Carbene Complexes

Transfer Hydrogenation of Carbonyl Compounds and Alkenes Catalyzed by Ruthenium(II)-N-Heterocycle Carbene Complexes

2007 ◽  
Vol 72 (8) ◽  
pp. 1037-1045 ◽  
Author(s):  
Marianna Fekete ◽  
Ferenc Joó
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Transfer ◽  
Transfer Hydrogenation ◽  
Unsaturated Alcohol ◽  
Two Phase ◽  
Carbene Complexes ◽  
Saturated Alcohol ◽  
Catalytic Activities ◽  
Saturated Aldehyde ◽  
Phase Mixture

The Ru(II)-N-heterocycle carbene complexes [RuCl2(η6-p-cymene)L] (L = 1-butyl-3-methylimid- azol-2-ylidene) and [RuCl(η6-p-cymene)L(pta)]Cl (pta = 1,3,5-triaza-7-phosphaadamantane) showed excellent catalytic activities (with turnover frequencies up to 1116 h-1) in the hydrogen transfer reduction of cinnamaldehyde and several ketones using propan-2-ol/KOH as a H-donor. Similar hydrogenations of trans-stilbene and cyclohexene were characterized by low conversions. The hydrogenation of 4-phenylbut-3-en-2-one and cinnamaldehyde proceeded with moderate selectivities of the formation of the saturated alcohol or of the of C=C hydrogenation (giving saturated ketone or saturated aldehyde). In the case of cinnamaldehyde, the unsaturated alcohol is initially formed; however, subsequent redox isomerization to the saturated aldehyde with the same catalyst diminishes its yield. The hydrogen transfer from formate to 4-phenylbut-3-en-2-one in an aqueous-organic two-phase mixture was also demonstrated.

Recyclable Covalent Triazine Framework-based Ru Catalyst for Transfer Hydrogenation of Carbonyl Compounds in Water

2019 ◽  
Vol 7 (9) ◽  
pp. 8893-8899 ◽  
Author(s):  
Sudakar Padmanaban ◽  
Gunniya Hariyanandam Gunasekar ◽  
Mearae Lee ◽  
Sungho Yoon
Keyword(s):  
Carbonyl Compounds ◽  
Transfer Hydrogenation ◽  
Ru Catalyst ◽  
Covalent Triazine Framework

scholarly journals Catalytic Activity of High-Surface-Area Amorphous MgO Obtained from Upsalite

Catalysts ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1338
Author(s):  
Marek Gliński ◽  
Ewa M. Iwanek (nee Wilczkowska) ◽  
Urszula Ulkowska ◽  
Agnieszka Czajka ◽  
Zbigniew Kaszkur
Keyword(s):  
Surface Area ◽  
Carbonyl Compounds ◽  
Main Product ◽  
High Surface ◽  
High Surface Area ◽  
Hydrogenation Reaction ◽  
Transfer Hydrogenation ◽  
Reaction Conditions ◽  
Synthesis Conditions ◽  
Transfer Hydrogenation Reaction

The first aim of the research was to synthesize a pure Upsalite, which is an amorphous form of MgCO3, by modifying a procedure described in the literature, so that it would be the precursor of a high-surface, amorphous magnesium oxide. The results indicate that within the studied reaction conditions, the type of alcohol used as the reactant has the most pronounced effect on the yield of reaction. From the two alcohols that led to the highest yield of Upsalite, methanol gave a substantially larger surface area (794 vs. 191 m2 g−1). The optimized synthesis conditions of Upsalite were used to obtain MgO via thermolysis, whose activity in the transfer hydrogenation reaction (THR) from ethanol, 2-propanol and 2-pentanol to various carbonyl compounds was determined. The optimal conditions for the thermolysis were as follows: vacuum, T = 673 K as the final temperature, and a heating rate of 2 deg min−1. The high-surface, amorphous magnesia (SBET = 488 m2 g−1) was found to be a very selective catalyst to 4-t-butylcyclohexanone in THR, which led to a diastereoselectivity of over 94% to the E-isomer of 4-t-butylcyclohexanol for more than 3 h, with conversions of up to 97% with either 2-propanol or 2-pentanol as the hydrogen donor. In the case of acrolein and 2-n-propylacrolein being used as the hydrogen acceptors, the unsaturated alcohol (UOL) was the main product of the reaction, with higher UOL yields noted for ethanol than 2-propanol.

Iron and chromium MOFs as sustainable catalysts for transfer hydrogenation of carbonyl compounds and biomass conversions

2020 ◽  
Vol 44 (20) ◽  
pp. 8223-8231 ◽  
Author(s):  
Punitharaj Vasanthakumar ◽  
Dharmalingam Sindhuja ◽  
Duraisamy Senthil Raja ◽  
Chia-Her Lin ◽  
Ramasamy Karvembu
Keyword(s):  
Carbonyl Compounds ◽  
Transfer Hydrogenation

Fe and Cr based MOFs (MIL-88B) act as efficient and reusable catalysts for transfer hydrogenation of carbonyl compounds including bio-derived substrates.

scholarly journals Transfer Hydrogenation from 2-propanol to Acetophenone Catalyzed by [RuCl2(η6-arene)P] (P = monophosphine) and [Rh(PP)2]X (PP = diphosphine, X = Cl−, BF4−) Complexes

Catalysts ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 162 ◽  
Author(s):  
Alberto Mannu ◽  
Arnald Grabulosa ◽  
Salvatore Baldino
Keyword(s):  
Transition Metals ◽  
Carbonyl Compounds ◽  
The Other ◽  
Transfer Hydrogenation ◽  
Chiral Alcohols ◽  
High Importance ◽  
Bidentate Phosphine ◽  
Turn Over Frequency ◽  
Turn Over ◽  
Reduction Of Ketones

The reduction of ketones through homogeneous transfer hydrogenation catalyzed by transition metals is one of the most important routes for obtaining alcohols from carbonyl compounds. The interest of this method increases when opportune catalytic precursors are able to perform the transformation in an asymmetric fashion, generating enantiomerically enriched chiral alcohols. This reaction has been extensively studied in terms of catalysts and variety of substrates. A large amount of information about the possible mechanisms is available nowadays, which has been of high importance for the development of systems with excellent outcomes in terms of conversion, enantioselectivity and Turn Over Frequency. On the other side, many mechanistic aspects are still unclear, especially for those catalytic precursors which have shown only moderate performances in transfer hydeogenation. This is the case of neutral [RuCl2(η6-arene)(P)] and cationic [Rh(PP)2]X (X = anion; P and PP = mono- and bidentate phosphine, respectively) complexes. Herein, a summary of the known information about the Transfer Hydrogenation catalyzed by these complexes is provided with a continuous focus on the more relevant mechanistic features.

Selective Reduction of Carbonyl Compounds via (Asymmetric) Transfer Hydrogenation on Heterogeneous Catalysts

Synthesis ◽  
2020 ◽  
Vol 52 (04) ◽  
pp. 504-520 ◽  
Author(s):  
Eszter Baráth
Keyword(s):  
Asymmetric Catalysis ◽  
Carbonyl Compounds ◽  
Heterogeneous Catalysts ◽  
Selective Reduction ◽  
Short Review ◽  
Transfer Hydrogenation ◽  
Chemical Transformations ◽  
Asymmetric Transfer Hydrogenation ◽  
Immobilized Catalysts ◽  
Main Challenge

Based on the ever-increasing demand for optically pure compounds, the development of efficient methods to produce such products is very important. Homogeneous asymmetric catalysis occupies a prominent position in the ranking of chemical transformations, with transition metals coordinated to chiral ligands being applied extensively for this purpose. However, heterogeneous catalysts have the ability to further extend the field of asymmetric transformations, because of their beneficial properties such as high stability, ease of separation and regeneration, and the possibility to apply them in continuous processes. The main challenge is to find potential synthetic routes that can provide a chemically and thermally stable heterogeneous catalyst having the necessary chiral information, whilst keeping the catalytic activity and enantioselectivity equally high (or even higher) than the corresponding homogeneous counterpart. Within this short review, the most relevant immobilization modes and preparative strategies depending on the support material used are summarized. From the reaction scope viewpoint, metal catalysts supported on the various solid materials studied in (asymmetric) transfer hydrogenation of carbonyl compounds are selected and represent the main focus of the second part of this overview.1 Introduction2 Synthesis of Chiral Heterogeneous Catalysts2.1 Immobilization of Homogeneous Asymmetric Catalysts2.1.1 Immobilization on Inorganic Supports2.1.2 Immobilization on Organic Polymers as Supports2.1.3 Immobilization on Dendrimer-Type Materials as Supports2.1.4 Self-Supported Chiral Catalysts: Coordination Polymers2.1.5 Immobilization Using Non-Conventional Media2.2 Chirally Modified Metal Surfaces for Heterogeneous Asymmetric Catalysis3 Examples of Transfer Hydrogenation on Heterogeneous Catalysts3.1 Silicon-Immobilized Catalysts3.2 Carbon-Material-Immobilized Catalysts3.3 Polymer-Immobilized Catalysts3.4 Magnetic-Nanoparticle-Immobilized Catalysts4 Conclusions

N-Benzyl Substituted N-Heterocyclic Carbene Complexes of Iridium(I): Assessment in Transfer Hydrogenation Catalyst

2013 ◽  
Vol 52 (18) ◽  
pp. 10601-10609 ◽  
Author(s):  
Süleyman Gülcemal ◽  
Aytaç Gürhan Gökçe ◽  
Bekir Çetinkaya
Keyword(s):  
Transfer Hydrogenation ◽  
Hydrogenation Catalyst ◽  
Carbene Complexes
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