Aluminium‐isopropylat als Reduktionsmittel. Eine allgemeine Methode zur Carbonylreduktion

Lund, Hakon

doi:10.1002/cber.19370700713

Cited by 71 publications

(19 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cyclic ethers such as [1,4]dioxane (39) and 2,3-dihydrofuran are known to donate a pair of hydrogen atoms to this type of compound. 2,3-Dihydro- [1,4]dioxine (41), the product of dioxane (39), is not able to donate another pair of hydrogen atoms [46,60,73,74]. These heterocyclic compounds are in general also very good solvents for both the catalyst and the substrates.…”

Section: Hydrogen Donorsmentioning

confidence: 99%

See 1 more Smart Citation

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Klomp¹,

Hanefeld²,

Peters³

2006

The Handbook of Homogeneous Hydrogenation

View full text Add to dashboard Cite

Section: Hydrogen Donorsmentioning

confidence: 99%

“…These authors reported the reduction of cyclohexanone (4) to cyclohexanol (5) in aqueous 2-propanol using chloroiridic acid (H 2 IrCl 6 ) (6) as catalyst (Scheme 20.2). In the initial experiments, turnover frequencies (TOF) of 200 h -1 were reported.…”

mentioning

confidence: 99%

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Klomp¹,

Hanefeld²,

Peters³

2006

The Handbook of Homogeneous Hydrogenation

View full text Add to dashboard Cite

“…The first transfer hydrogenation (in 1925) was discovered by Meerwein and Schmidt using alcohols as the H-source in the presence of aluminium alkoxide as a homogeneously acting catalyst for the reduction of carbonyl compounds [3] (further opportunities towards additional applicability of the reaction were studied by Verley [4], Ponndorf [5], and Lund [6]). Later on, reversing of the reaction was applied in oxidation reactions and was studied by Oppenauer [7].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Transfer Reactions of Carbonyls, Alkynes, and Alkenes with Noble Metals in the Presence of Alcohols/Ethers and Amines as Hydrogen Donors

Baráth

2018

Catalysts

View full text Add to dashboard Cite

Hydrogen transfer reactions have exceptional importance, due to their applicability in numerous synthetic pathways, with academic as well as industrial relevance. The most important transformations are, e.g., reduction, ring-closing, stereoselective reactions, and the synthesis of heterocycles. The present review provides insights into the hydrogen transfer reactions in the condensed phase in the presence of noble metals (Rh, Ru, Pd) as catalysts. Since the H-donor molecules (such as alcohols/ethers and amines (1°, 2°, 3°)) and the acceptor molecules (alkenes (C=C), alkynes (C≡C), and carbonyl (C=O) compounds) play a crucial role from mechanistic viewpoints, the present summary points out the key mechanistic differences with the interpretation of current contributions and the corresponding historical achievements as well.

show abstract

“…Verley [2] and Meerwein and Schmidt [3] discovered independently in 1925 that aldehydes could be reduced to the corresponding primary alcohol using ethanol in the presence of aluminium ethoxide. [5]. The versatility and selectivity of the reaction was demonstrated in the selective reduction of carbonyl functionalities in the presence of other reducible groups such as C=C, nitro groups, esters, etc.…”

Section: Introductionmentioning

confidence: 99%

Meerwein-Ponndorf-Verley Reduction over Heterogeneous Catalysts

Chuah¹,

Jaenicke

Zhu³

et al. 2006

COC

123

View full text Add to dashboard Cite

The Meerwein-Ponndorf-Verley (MPV) transfer hydrogenation of aldehydes and ketones to the corresponding alcohols is distinguished by its exceptional chemoselectivity. This reaction is particularly suited for the reduction of unsaturated aldehydes and ketones, compared to catalytic reductions with molecular hydrogen using noble metal catalysts. The MPV reaction has traditionally been carried out using homogeneous catalysts like aluminium or titanium alkoxides. However, over the past two decades, an increasing number of reports on heterogeneous catalysts for the MPV reaction have been published. This interest is stimulated by the advantages of heterogeneous over homogeneous catalysis, particularly for larger-scale applications. The article provides a critical review of the recent literature on heterogeneous catalysts for the MPV reaction. The materials include hydrotalcites, metal oxides such as magnesium oxide, zirconia, silica and alumina, alkoxides of Al, La, Zr and Hf grafted to high surface area mesoporous materials, and zeolites. In particular, zeolite beta has been found to be a highly stereoselective catalyst in the MPV reduction of 4-tertbutylcyclohexanone, giving predominantly cis-4-tert-butylcyclohexanol rather than the thermodynamically stable transalcohol. The activity was improved with the incorporation of other metals such as Ti, Sn and Zr. These materials show good tolerance to moisture, lack of leaching and ease of regeneration, thus making them useful catalysts in MPV reduction. The activity of a catalyst depends on its ligand exchange capability with the reductant with a high ligand exchange rate enabling the use of catalytic amounts.

show abstract

Aluminium‐isopropylat als Reduktionsmittel. Eine allgemeine Methode zur Carbonylreduktion

Cited by 71 publications

References 6 publications

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Hydrogen Transfer Reactions of Carbonyls, Alkynes, and Alkenes with Noble Metals in the Presence of Alcohols/Ethers and Amines as Hydrogen Donors

Meerwein-Ponndorf-Verley Reduction over Heterogeneous Catalysts

Contact Info

Product

Resources

About