Recent developments in the homogeneous hydrogenation of carboxylic acid esters

Clarke, Matthew L.

doi:10.1039/c2cy20601c

Cited by 105 publications

(49 citation statements)

References 32 publications

(9 reference statements)

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“…Soon after the authors observed that this reduction is not specific for the acetoxy group, and completed reduction of esters 34 to ethers 35, whereby the complex NaBH 4 /BF 3 …”

Section: Methodsmentioning

confidence: 99%

“…This process includes the following steps; (i) initial transmetalation between InBr 3 and Et 3 SiH, (ii) formation of a radical intermediate, consecutive split of the H atom from Et 3 SiH and formation of the radical ether product, (iii) and in the final step the indium radical species is regenerated.…”

Section: Scheme 19mentioning

confidence: 99%

“…In analogy to addition of silanes to the carbonyl group, the mechanism of reduction was proposed (Scheme 15). 68 Cl 3 SiH/-rays Cl 3 SiH + Cl 3 SiH + Cl 3 Si-O-SiCl 3…”

Section: Reductions By Silanes and Lewis Acidsmentioning

confidence: 99%

“…In another mini-review recent developments in the homogeneous hydrogenation of carboxylic acid esters were highlighted. 3 However only the process which leads to alcohols were discussed, and limited practicability of various sophisticated transition metal complexes revealed. An interesting aspect of selective reduction of esters is their partial reduction to aldehydes, which are known as more reactive species under a variety of reducing conditions.…”

Section: Introductionmentioning

confidence: 99%

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Ethers from esters; from exceptional transformation to synthetic method

Jakopović¹,

Kapić²,

Alihodžić³

et al. 2015

Arkivoc

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Most ether-bond forming reactions based on traditional methods or modifications thereof require strongly acidic or basic conditions and often harsh reaction conditions. Reduction of esters to ethers has been regarded as an impracticable method, generally affording alcohols as the principal products. Only recently, original, mostly catalytic methods for reduction of esters to ethers have been reported, which proceed under mild conditions and are compatible with many functional groups present in the substrate ester molecule. These reactions are considered as a valuable alternative to traditional methods, and specific protocols have been reported. An account of the progress in this synthetic methodology is given.

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“…Soon after the authors observed that this reduction is not specific for the acetoxy group, and completed reduction of esters 34 to ethers 35, whereby the complex NaBH 4 /BF 3 …”

Section: Methodsmentioning

confidence: 99%

Section: Scheme 19mentioning

confidence: 99%

“…In analogy to addition of silanes to the carbonyl group, the mechanism of reduction was proposed (Scheme 15). 68 Cl 3 SiH/-rays Cl 3 SiH + Cl 3 SiH + Cl 3 Si-O-SiCl 3…”

Section: Reductions By Silanes and Lewis Acidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ethers from esters; from exceptional transformation to synthetic method

Jakopović¹,

Kapić²,

Alihodžić³

et al. 2015

Arkivoc

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“…[14] We envisioned that the transition-metal complexes 1a-l (Figure 1), with their robust nature and well-defined pincertype structures, [15] might be worthwhile candidates for the catalysis of N-formylation reactions.S ome of the complexes have been shown to be excellent catalysts for the hydrogenation of various carboxylic and carbonic acid derivatives. [16,17] Encouraged by these facts,w ei nitiated the study with N-formylation of morpholine (2a)asthe model reaction and the Ru/PNP pincer complex 1b as the catalyst. A preliminary survey of various reaction parameters,i ncluding temperature,C O 2 /H 2 partial pressures,a nd solvent was performed under ac atalyst loading of 0.1 mol %i nt he presence of 0.1 mol % tBuOK, and the results are summarized in Table S2 (see the Supporting Information).…”

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confidence: 99%

Highly Efficient Ruthenium‐Catalyzed N‐Formylation of Amines with H₂ and CO₂

et al. 2015

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Ah ighly efficient catalyst system based on ruthenium-pincer-type complexes has been discovered for N-formylation of various amines with CO 2 and H 2 ,t hus affording the corresponding formamides with excellent productivity (turnover numbers of up to 1940 000 in as ingle batch)a nd selectivity.U sing as imple catalyst recycling protocol, the catalyst was reused for 12 runs in N,N-dimethylformamide production without significant loss of activity,thus demonstrating the potential for practical utilization of this costeffective process.Aone-pot two-step procedure for hydrogenation of CO 2 to methanol via the intermediacy of formamide formation has also been developed.

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Hydrogenation and Dehydrogenation

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2023

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1 Hydrogenation 1.1 Thermodynamics 1.2 Kinetics 1.3 Catalysts 1.3.1 Active Metals 1.3.2 Catalyst Carrier 1.3.3 Catalyst Additives 1.3.4 Catalyst Poisoning and Mechanical Destruction 1.3.5 Activation/Reduction of Hydrogenation Catalysts 1.4 Solvents and Additives 1.5 Hydrogenation Processes 1.5.1 Slurry Hydrogenation 1.5.2 Fixed‐Bed Liquid Hydrogenation 1.5.3 Vapor‐Phase Hydrogenation 1.6 Homogeneously Catalyzed Hydrogenation 1.7 Transfer Hydrogenation 1.8 Reduction with Complex Hydrides 1.9 Hydrogenation of Individual Compounds 1.9.1 Hydrogenation of Olefins 1.9.2 Hydrogenation of Alkynes and Dienes 1.9.3 Hydrogenation of Aromatic Rings 1.9.4 Hydrogenation of Aldehydes 1.9.5 Hydrogenation of Ketones 1.9.6 Hydrogenation of Esters 1.9.7 Hydrogenation of Carboxylic Acids 1.9.8 Hydrogenation of Nitro Compounds 1.9.9 Hydrogenation of Nitriles 1.9.10 Selective Hydrogenation Reactions 1.9.11 Homogeneous Hydrogenations 2 Dehydrogenations 2.1 Dehydrogenation Catalysts 2.2 Coking and Catalyst Regeneration 2.3 Steam Addition 2.4 Process Concepts 2.4.1 Isothermal Process 2.4.2 Adiabatic Process 2.5 Dehydrogenation of Individual Compounds 2.5.1 Alkane‐to‐Olefin Dehydrogenation 2.5.2 Dehydrogenation of Alcohols References

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Recent developments in the homogeneous hydrogenation of carboxylic acid esters

Cited by 105 publications

References 32 publications

Ethers from esters; from exceptional transformation to synthetic method

Ethers from esters; from exceptional transformation to synthetic method

Highly Efficient Ruthenium‐Catalyzed N‐Formylation of Amines with H₂ and CO₂

Hydrogenation and Dehydrogenation

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Recent developments in the homogeneous hydrogenation of carboxylic acid esters

Cited by 105 publications

References 32 publications

Ethers from esters; from exceptional transformation to synthetic method

Ethers from esters; from exceptional transformation to synthetic method

Highly Efficient Ruthenium‐Catalyzed N‐Formylation of Amines with H2 and CO2

Hydrogenation and Dehydrogenation

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Product

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Highly Efficient Ruthenium‐Catalyzed N‐Formylation of Amines with H₂ and CO₂