Efficient Construction of 4-hydroxy-4-arylbutan-2-ones through an Enantioselective Aldol Reaction Mediated by a Recoverable Proline-Based Chiral Ionic Liquid

2020 ◽  
Vol 42 (2) ◽  
pp. 243-243
Author(s):  
Dao Cai Wang Dao Cai Wang ◽  
Cong Wu Cong Wu ◽  
Chi Zhang Chi Zhang ◽  
Fang Zhen Zhou Fang Zhen Zhou ◽  
Hang Song and Xiao Peng Liu Hang Song and Xiao Peng Liu
Keyword(s):  
Ionic Liquid ◽  
Column Chromatography ◽  
Aldol Reaction ◽  
Reaction Medium ◽  
Aromatic Aldehydes ◽  
Catalytic Method ◽  
Mild Conditions ◽  
Satisfactory Performance ◽  
Efficient Construction ◽  
Chiral Ionic Liquid

Chiral ionic liquid derived from L-proline worked as an excellent organocatalyst for the enantioselective aldol reaction of aromatic aldehydes and acetone. The reaction was conducted in the presence of [BMIM][BF4] as reaction medium. The substrate scope of aldol reaction was successfully explored for various aromatic aldehydes under the mild conditions. The generated aldol products were separated by column chromatography with moderate to good yields as well as enantioselectivities. The main advantage of this catalytic method was that the catalyst and solvent could be recovered at the same time and reused for at least five times with satisfactory performance.

scholarly journals Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

2019 ◽  
Vol 15 ◽  
pp. 2907-2913 ◽  
Author(s):  
László Orha ◽  
József M Tukacs ◽  
László Kollár ◽  
László T Mika
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Reaction Medium ◽  
Cross Coupling ◽  
Environmental Efficiency ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Mild Conditions ◽  
Palladium Catalyzed ◽  
Alternative Reaction Medium

It was demonstrated that the γ-valerolactone-based ionic liquid, tetrabutylphosphonium 4-ethoxyvalerate as a partially bio-based solvent can be utilized as alternative reaction medium for copper- and auxiliary base-free Pd-catalyzed Sonogashira coupling reactions of aryl iodides and functionalized acetylenes under mild conditions. Twenty-two cross-coupling products were isolated with good to excellent yields (72–99%) and purity (>98%). These results represent an example which proves that biomass-derived safer solvents can be utilized efficiently in common, industrially important transformations exhibiting higher chemical and environmental efficiency.

Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles

2015 ◽  
Vol 5 (7) ◽  
pp. 3728-3734 ◽  
Author(s):  
He-yan Jiang ◽  
Xu-xu Zheng
Keyword(s):  
Ionic Liquid ◽  
Aromatic Aldehydes ◽  
Ruthenium Nanoparticles ◽  
Aromatic Ketones ◽  
Functionalized Ionic Liquid ◽  
Mild Conditions ◽  
Chemoselective Hydrogenation

Aromatic ketones, aromatic aldehydes and quinolines can be hydrogenated with switchable excellent chemoselectivity under mild conditions catalyzed by ruthenium nanoparticles.

InCl3×4H2O/TMSCl-Catalyzed Aldol Reaction of Aromatic Aldehydes with Cycloalkanones in Ionic Liquid Medium.

ChemInform ◽  
2005 ◽  
Vol 36 (16) ◽  
pp. no-no
Author(s):  
Xueyuan Hu ◽  
Xuesen Fan ◽  
Xinying Zhang ◽  
Jianji Wang
Keyword(s):  
Ionic Liquid ◽  
Liquid Medium ◽  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Ionic Liquid Medium

scholarly journals An Investigation of the Enolization and Isomeric Products Distribution in the Water Promoted Aldol Reaction of Tropinone and Granatanone

2016 ◽  
Vol 2016 ◽  
pp. 1-15 ◽  
Author(s):  
Ryszard Lazny ◽  
Artur Ratkiewicz ◽  
Krzysztof Brzezinski ◽  
Aneta Nodzewska ◽  
Katarzyna Sidorowicz
Keyword(s):  
Aldol Reaction ◽  
Reaction Medium ◽  
Aromatic Aldehydes ◽  
Aldol Reactions ◽  
Free Energies ◽  
Thermodynamic Control ◽  
Dft Methods ◽  
Aldol Addition ◽  
Aqueous Conditions ◽  
D Model

The exo,anti/exo,syn-diastereoselectivity of water promoted direct aldol reactions of tropinone and granatanone (pseudopelletierine) is strongly dependent on the amount of water added and aromatic aldehyde used. DFT methods were applied to calculate the free energies of tropinone and granatanone enols, transition states, and isomeric aldol products. A theoretical model was verified by comparison of results from several DFT methods and functionals with experiments. The 6-31g(d)/CPCM method proved most suited to the problem, although all methods tested predicted similar trends. Explicit inclusion of a water molecule bonded to the amino ketones resulted in increased stability of the enol forms. The dependence of the anti/syn-diastereoselectivity on the amount of water used may be rationalized on the basis of change in the polarity of the reaction medium. The predicted stabilities of competing products agreed with experimental results supporting the notion of thermodynamic control. The isomeric products distributions for the aldol reaction of several aromatic aldehydes in solventless (neat) conditions were accurately calculated from free energies of the aldol addition step in the gas phase using B3LYP/6-31g(d) method and in aqueous conditions using the CPCM-B3LYP/6-31g(d) model. Our methodology can be useful for predicting the outcome of this type of aldol reactions.

Copper-catalysed difluoroalkylation of aromatic aldehydes via a decarboxylation/aldol reaction

2017 ◽  
Vol 15 (36) ◽  
pp. 7654-7659 ◽  
Author(s):  
Jin-Wei Yuan ◽  
Shuai-Nan Liu ◽  
Wen-Peng Mai
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Mild Conditions

A copper-catalysed tandem decarboxylation/aldol reaction of simple aromatic aldehydes with 2,2-difluoro-3-oxo-3-arylpropanoic acid under mild conditions.

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