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.

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.

(S,S,S)-Perhydroindolic Acid: Efficient Catalyst for Direct Asymmetric Aldol Reaction from Aromatic Aldehydes.

ChemInform ◽  
2007 ◽  
Vol 38 (3) ◽  
Author(s):  
Xiaoping Tang ◽  
Benoit Liegault ◽  
Jean-Luc Renaud ◽  
Christian Bruneau
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Efficient Catalyst ◽  
Asymmetric Aldol ◽  
Asymmetric Aldol Reaction

HMPA Promotes Retro-Aldol Reaction, Resulting in Syn-Selective Addition of Lithiated 1-Naphthylacetonitrile to Aromatic Aldehydes

2000 ◽  
Vol 2 (16) ◽  
pp. 2443-2445 ◽  
Author(s):  
Paul R. Carlier ◽  
Cedric W.-S. Lo ◽  
Michael M.-C. Lo ◽  
Nan Chi Wan ◽  
Ian D. Williams
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Selective Addition

ChemInform Abstract: Highly Enantioselective Proline-Catalyzed Direct Aldol Reaction of Chloroacetone and Aromatic Aldehydes.

ChemInform ◽  
2012 ◽  
Vol 43 (37) ◽  
pp. no-no
Author(s):  
Angel Martinez-Castaneda ◽  
Belen Poladura ◽  
Humberto Rodriguez-Solla ◽  
Carmen Concellon ◽  
Vicente del Amo
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Direct Aldol Reaction

Highly Enantioselective Proline-Catalysed Direct Aldol Reaction of Chloroacetone and Aromatic Aldehydes

2012 ◽  
Vol 18 (17) ◽  
pp. 5188-5190 ◽  
Author(s):  
Ángel Martínez-Castañeda ◽  
Belén Poladura ◽  
Humberto Rodríguez-Solla ◽  
Carmen Concellón ◽  
Vicente del Amo
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Direct Aldol Reaction

scholarly journals Low Temperature Chemoselective Hydrogenation of Aldehydes over a Magnetic Pd Catalyst

2019 ◽  
Vol 9 (9) ◽  
pp. 1792
Author(s):  
Liu ◽  
Wang ◽  
Gao ◽  
Wang ◽  
Cheng ◽  
...  
Keyword(s):  
Low Temperature ◽  
Room Temperature ◽  
Heterogeneous Catalysts ◽  
Aromatic Aldehydes ◽  
Pd Catalyst ◽  
Primary Alcohols ◽  
Mild Conditions ◽  
Excellent Yield ◽  
Chemoselective Hydrogenation ◽  
Supported Palladium

Chemoselective hydrogenation of aldehydes with heterogeneous catalysts under mild conditions is of great importance but remains a major challenge. Herein, an efficient strategy was developed for low temperature chemoselective hydrogenation of aldehydes with broad substrate scope over a magnetic material supported palladium catalyst (γ-Fe2O3@HAP-Pd). Aldehydes bearing various reducible functional groups readily underwent hydrogenation to give the corresponding primary alcohols with moderate to excellent yield at room temperature in aqueous solutions. The Hammett equation revealed that the hydrogenation of aromatic aldehydes proceeded via an anionic intermediate. Additionally, when the temperature increased to 70 °C, toluene was obtained by the deoxygenation of benzaldehyde in excellent yield. Furthermore, the γ-Fe2O3@HAP-Pd could be recycled up to six times without loss of activity and metal leaching.

scholarly journals Bioinspired Polymer-Bound Organocatalysts for Direct Asymmetric Aldol Reaction: Experimental and Computational Studies

Catalysts ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 398
Author(s):  
Ganhong Du ◽  
Jun Ling ◽  
Fangyu Hu ◽  
Keyuan Liu ◽  
Long Ye ◽  
...  
Keyword(s):  
Theoretical Calculations ◽  
Aldol Reaction ◽  
Catalytic Efficiency ◽  
Aromatic Aldehydes ◽  
Relative Energy ◽  
Catalyst Loading ◽  
Polymer Backbone ◽  
Asymmetric Aldol ◽  
Tertiary Amide ◽  
Asymmetric Aldol Reaction

A series of poly(2-oxazoline) (POX) derivatives bearing prolinamide pendants were designed as organocatalysts and evaluated in the direct asymmetric aldol reaction between aromatic aldehydes and cyclic ketones. The structural variation of the alkyl spacer connecting the polymer backbone with the catalytic unit was applied so as to deduce structure–performance relationships combined with comparable experiments from model catalysts. Results showed that the POX-bound prolinamides can promote the aldol reaction more effectively as compared to their small-molecular and non-POX-bound analogs. The catalyst P3 containing the pyrrolidine moiety closer to the tertiary amide backbone exhibited the overall best catalytic efficiency, affording anti-products in 84% yield with 89% ee in the representative aldol addition of cyclohexanone to 4-nitrobenzaldehyde at a 10 mol.% catalyst loading. Furthermore, the influence of trifluoroacetic acid as an additive on the asymmetric transformation was investigated. Theoretical calculations revealed that the protonation of the aldehyde carbonyl group switched the activation mode of the aldol acceptor through hydrogen bond interactions, thereby changing the relative energy barrier of the enamine/aldehyde reaction transition states, which accounted well for the significant improvement in the enantioselectivity of the acidic additives observed experimentally.

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