Homogeneous catalytic hydrogenation of carboxylic acid esters to alcohols

Grey, Roger A.; Pez, Guido P.; Wallo, Andrea; Corsi, Jeff

doi:10.1039/c39800000783

Cited by 67 publications

(34 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Fairweather showed that C 10 -C 16 fatty esters could be reduced into the corresponding alcohols, precursors of plasticizers and surfactants [49]. Finally, chemoselective hydrogenation of methyl esters in the presence of olefin, hindered acetate, carbamate, secondary and tertiary amides has been elegantly illustrated by Beller with a pharmaceutically relevant dodecapeptide (Scheme 40) [41].…”

Section: Edited Jan 19mentioning

confidence: 98%

Iron-catalyzed reduction of carboxylic and carbonic acid derivatives

Merel

Tran

Gaillard

et al. 2015

Coordination Chemistry Reviews

102

View full text Add to dashboard Cite

Section: Edited Jan 19mentioning

confidence: 98%

Iron-catalyzed reduction of carboxylic and carbonic acid derivatives

Merel

Tran

Gaillard

et al. 2015

Coordination Chemistry Reviews

102

View full text Add to dashboard Cite

“…Keywords: 1,2-amino alcohol; a-amino ester and ahydroxy ester; 1,2-diol; catalytic hydrogenation drogenation of electron-deficient esters [16,17] also needed T > 100°C and high pressure, or were only active for a very limited range of substrates.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

Studer¹,

Burkhardt²,

Blaser³

2001

Adv. Synth. Catal.

View full text Add to dashboard Cite

The hydrogenation of carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various α‐amino and α‐hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields of the desired amino alcohols and diols were obtained without racemization. The most suitable α‐substituents were NH2, NHR, and OH, whereas β‐NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was found for α‐NR2, α‐OR, and unfunctionalized esters; acids and amides were also not reduced under these conditions. A working hypothesis for the mode of action of the catalyst is presented.

show abstract

“…First detailed studies on the hydrogenation of nitriles in the presence homogeneous catalysts were performed by Pez 35 and Grey 36 in the early 80's. Recent progress is mainly achieved using ruthenium-based catalysts, which is also highlighted in a patent by Beatty and Paciello 37 .…”

mentioning

confidence: 99%

Mild and selective hydrogenation of aromatic and aliphatic (di)nitriles with a well-defined iron pincer complex

et al. 2014

View full text Add to dashboard Cite

The catalytic hydrogenation of carboxylic acid derivatives represents an atom-efficient and clean reduction methodology in organic chemistry. More specifically, the selective hydrogenation of nitriles offers the possibility for a green synthesis of valuable primary amines. So far, this transformation lacks of useful, broadly applicable non-noble metal-based catalyst systems. In the present study, we describe a molecular-defined iron complex, which allows for the hydrogenation of aryl, alkyl, heterocyclic nitriles and dinitriles. By using an iron PNP pincer complex, we achieve very good functional group tolerance. Ester, ether, acetamido as well as amino substituents are not reduced in the presence of nitriles. Moreover, nitriles including an α,β-unsaturated double bond and halogenated derivatives are well tolerated in this reaction. Notably, our complex constitutes the first example of an homogeneous catalyst, which permits the selective hydrogenation of industrially important adipodinitrile to 1,6-hexamethylenediamine.

show abstract

Homogeneous catalytic hydrogenation of carboxylic acid esters to alcohols

Cited by 67 publications

References 0 publications

Iron-catalyzed reduction of carboxylic and carbonic acid derivatives

Iron-catalyzed reduction of carboxylic and carbonic acid derivatives

Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

Mild and selective hydrogenation of aromatic and aliphatic (di)nitriles with a well-defined iron pincer complex

Contact Info

Product

Resources

About