129277-18-5Relevant academic research and scientific papers
A novel simple bifunctional catalyst for the direct aldol reaction
Liu, Chang Lu,Zhang, Hao,Wang, Ning
, p. 651 - 654 (2011)
Direct aldol reactions of aldehydes and ketones can proceed smoothly in the presence of a catalytic amount of naphthol/sodium naphtholate (5 mol%) to afford the corresponding products with yields up to 98%. Such a bifunctional catalyst is more moderate than strong acid or base employed in direct aldol reactions.
Biomass waste-derived recyclable heterogeneous catalyst for aqueous aldol reaction and depolymerization of PET waste
Khiangte, Vanlalngaihawma,Laldinpuii, Z. T.,Lalhmangaihzuala, Samson,Lalmuanpuia, Chhakchhuak,Pachuau, Zodinpuia,Vanlaldinpuia, Khiangte
, p. 19542 - 19552 (2021/11/09)
In this work, we discuss the valorization of biomass waste-derived orange peel ash (OPA) by exploring its applicability as a heterogeneous catalyst in aqueous aldol reactions and demonstrating its versatility by promoting the methanolysis of poly(ethylene terephthalate) (PET) waste. The catalyst was characterized using Fourier-transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET) analysis, X-ray powder diffraction (XRD), X-ray fluorescence (XRF), energy dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and thermal gravimetric analysis (TGA) to decode its chemical composition. The aldol reactions were carried out at ambient temperature in the presence of water as a solvent. PET depolymerization was performed in an autoclave for 1 h using only 6% w/w OPA. The catalyst was recovered and reused in both the reactions for up to four successive cycles with minimal loss in the catalytic activity. The use of OPA as a cost-free, eco-friendly and effective recyclable catalyst enables a greener route for C-C bond formation and PET waste recycling.
MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati
, p. 6115 - 6125 (2020/10/27)
Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.
A Mild Procedure for Enone Preparation Catalysed by Bovine Serum Albumin in a Green and Easily Available Medium
Ardanaz, Sebastián M.,Velez Rueda, Ana J.,Parisi, Gustavo,Iribarren, Adolfo M.,Iglesias, Luis E.
, p. 1750 - 1757 (2018/04/24)
Abstract: A simple and mild procedure to obtain α,β-unsaturated ketones from acetone and a set of benzaldehydes is described. The approach applies bovine serum albumin (BSA) catalysis and water or ethanol, this mild reaction medium contrasting with the strong reaction conditions of the classic aldol condensation. Except for the assayed nitrobenzaldehydes, high enone yields (88–97%) were attained. In addition to its mildness, further advantages of this procedure are the use of a green catalyst exhibiting an efficient reuse and the use of eco-friendly and cheap solvents. In order to gain a deeper understanding of the involved catalytic mechanism, computational experiments on BSA structural analysis and molecular docking were carried out.
One-pot bienzymatic cascade combining decarboxylative aldol reaction and kinetic resolution to synthesize chiral β-hydroxy ketone derivatives
Xu, Fan,Xu, Jian,Hu, Yujing,Lin, Xianfu,Wu, Qi
, p. 76829 - 76837 (2016/08/30)
A bienzymatic one-pot sequential cascade for the synthesis of (S)-β-hydroxy ketones and acylated (R)-β-hydroxy ketone derivatives was successfully developed. An immobilized lipase from Mucor miehei (MML) catalysed promiscuous decarboxylative aldol reaction and a lipase A or B from Candida antarctica (CAL-A or CAL-B) catalysed kinetic resolution of racemic β-hydroxy ketone were combined in this one-pot protocol, reducing the purification step between the two reactions. Twelve chiral β-hydroxy ketones and the same number of corresponding acylated derivatives were obtained with excellent ee values and high yields through this method, and the scaling up experiment also worked without apparent loss of reaction rate and stereoselectivity.
Catalyst-free aldol reaction in a water medium
Yao, Weirong,Cui, Yanli,Wang, Peipei,Mao, Yangyi
, p. 293 - 296 (2016/05/24)
Background: With growing interest in developing environmentally friendly reactions and atom-economic processes in recent years, the utilization of water as a solvent has attracted a great deal of attention. This is not only for its low-cost, safe and envi
Application of Deep Eutectic Solvents in Promiscuous Lipase-Catalysed Aldol Reactions
González-Martínez, Daniel,Gotor, Vicente,Gotor-Fernández, Vicente
supporting information, p. 1513 - 1519 (2016/04/05)
The application of deep eutectic solvents has been demonstrated for the first time in promiscuous lipase-catalysed aldol reactions. The model reaction between 4-nitrobenzaldehyde and acetone was examined in depth, with excellent compatibility being found between porcine pancreas lipase and choline chloride/glycerol mixtures for the formation of the aldol product in high yields. The system was compatible with a series of aromatic aldehydes and ketones including acetone, cyclopentanone and cyclohexanone. In some cases, the corresponding α,β-unsaturated carbonyl compounds were found as minor products. Control experiments demonstrate that the enzymatic preparation was also responsible for a collateral dehydration reaction once the aldol product is formed. Deep eutectic solvents are used for the first time in promiscuous lipase-catalysed aldol reactions. The reaction between substituted benzaldehydes and aliphatic ketones has excellent compatibility with porcine pancreas lipase (PPL) and choline chloride/glycerol mixtures and gives the aldol product in high yields. PPL was also responsible for a collateral dehydration reaction.
Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols
Bethi, Venkati,Fernandes, Rodney A.
, p. 8577 - 8584 (2016/09/28)
A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based synthesis of α,β-unsaturated and nonconjugated methyl ketones is demonstrated.
PH-Tuned modulation of 1d chain to 3d metal-organic framework: Synthesis, structure and their useful application in the heterogeneous claisen-Schmidt reaction
Sen, Rupam,Saha, Debraj,Koner, Subratanath,Mal, Dasarath,Brando, Paula,Lin, Zhi
, p. 591 - 598 (2015/03/14)
The role of pH in the formation of metal-organic frameworks (MOFs) has been studied on magnesium-based carboxylate framework systems [Mg(Pdc)(H2O)3]n (1) and [Mg(Pdc)(H2O)]n (2) (Pdc=pyridine-2,3-dica
A photoswitchable organocatalyst based on a catalyst-imprinted polymer containing azobenzene
Liu, Hua-Dong,Zheng, An-Xun,Gong, Cheng-Bin,Ma, Xue-Bing,Hon-Wah Lam, Michael,Chow, Cheuk-Fai,Tang, Qian
, p. 62539 - 62542 (2015/08/06)
An l-proline-catalyzed aldol reaction was photo-controlled using an l-proline-imprinted polymer containing azobenzene. Upon UV irradiation, azobenzene chromophores underwent trans → cis isomerization, thereby releasing l-proline to catalyze the aldol reac
