1218-89-9Relevant academic research and scientific papers
Efficient and mild benzoin condensation reaction catalyzed by simple 1-N-alkyl-3-methylimidazolium salts
Xu, Li-Wen,Gao, Yang,Yin, Jian-Jun,Li, Lyi,Xia, Chun-Gu
, p. 5317 - 5320 (2005)
The benzoin reaction, catalyzed by simple 1-N-alkyl-3-methylimidazolium salt-based ionic liquid via carbene intermediate, to give the α-hydroxyl ketone proceeds in CH2Cl2 under mild conditions.
Reduction of 1,2-dicarbonyl compounds mediated by the combination of phosphine and lewis acid
Kikuchi, Satoshi,Hashimoto, Yukihiko
, p. 1267 - 1269 (2004)
The combination of Ph3P/AlBr3 effectively promoted the reduction of several 1,2-dicarbonyl compounds in the presence of water (1.0 equiv) and the corresponding α-hydroxy carbonyl compounds were obtained in good yields.
A new protocol for one-pot synthesis of tetrasubstituted pyrroles using tungstate sulfuric acid as a reusable solid catalyst
Farahi, Mahnaz,Davoodi, Mahdiyeh,Tahmasebi, Mina
, p. 1582 - 1584 (2016)
A variety of tetrasubstituted pyrroles were synthesized in good yields in a one-pot, three-component reaction of α-hydroxyketones, malononitrile, and ammonium acetate using tungstate sulfuric acid (TSA) under solvent-free conditions.
N-PEGylated Thiazolium Salt: A Green and Reusable Homogenous Organocatalyst for the Synthesis of Benzoins and Acyloins
Haghighi, Ali Javaheri,Mokhtari, Javad,Karimian, Khashayar
, p. 1646 - 1652 (2020/10/19)
N-PEGylated-thiazolium salt is used as efficient catalyst for the benzoin condensation. The catalyst was synthesized by reaction of activated polyethylene glycol 10,000 (PEG-10000) with 4-methyl-5-thiazoleethanol (sulfurol). Reaction mixture undergoes temperature-assisted phase transition and catalyst separated by simple filtration. After reaction course, catalyst can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence ecofriendly. Synthesized benzoins and acyloins by this method have been characterized on the basis of melting point and 1H-NMR spectral studies. Graphic Abstract: [Figure not available: see fulltext.]
Organocatalytic Synthesis of Substituted Vinylene Carbonates
Onida, Killian,Haddleton, Alice J.,Norsic, Sébastien,Boisson, Christophe,D'Agosto, Franck,Duguet, Nicolas
supporting information, p. 5129 - 5137 (2021/09/18)
The organocatalytic synthesis of substituted vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90 °C under solvent-free conditions. A wide range of substituted vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20–99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (>30 g after 5 runs). (Figure presented.).
Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source
Shen, Guoli,Liu, Haojie,Chen, Jingchao,He, Zhenxiu,Zhou, Yongyun,Wang, Lin,Luo, Yang,Su, Zhimin,Fan, Baomin
supporting information, p. 3601 - 3610 (2021/05/04)
The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is
Preparation and Application of Silica Films Supported Imidazolium-Based Ionic Liquid as Efficient and Recyclable Catalysts for Benzoin Condensations
Qian, Cunwei,Yao, Changsheng,Yang, Liujun,Yang, Bo,Liu, Shuchun,Liu, Zongtang
, p. 1389 - 1396 (2019/11/21)
Abstract: Two silica films -immobilized imidazolium-based ionic liquids (TMICl @silica films) were prepared, characterized and utilized as efficient catalysts for the benzoin reaction. Combined characterization results from FT-IR, elemental analysis, N2 adsorption–desorption isotherms and SEM, suggested that the imidazolium-based ionic liquids were successfully immobilized on the silica films. Moreover, the catalytic performance tests demonstrated that silica films immobilized imidazolium-based ionic liquids (ILs) exhibited excellent activity for the benzoin reactions of aromatic aldehydes. The influence of catalyst concentration, temperature and reaction duration on the catalytic activity were investigated by employing 0.7TMICl @silica film(catalyst C) as the catalyst. The results also showed that the benzoin condensations of aromatic aldehydes could give desired products with satisfactory yields under the optimized conditions. Additionally, the catalyst can be effortlessly separated by filtration and reused more than five times without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]
N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling
Nicholson, William I.,Seastram, Alex C.,Iqbal, Saqib A.,Reed-Berendt, Benjamin G.,Morrill, Louis C.,Browne, Duncan L.
, p. 131 - 135 (2019/12/11)
The ability to conduct N-heterocyclic carbene-catalysed acyl anion chemistry under ball-milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular-benzoin, intramolecular-benzoin, intermolecular-Stetter and intramolecular-Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent-minimised conditions.
1-butyl-3-methylimidazolium bromide as a solvent and precatalyst for stetter reaction
Phungpis, Baramee,Hahnvajanawong, Viwat
, p. 2028 - 2032 (2020/09/02)
Stetter reaction between aromatic aldehydes and acrylonitrile/ethyl acrylate performing in [Bmim]Br in the presence of NaOH is described. N-Heterocyclic carbene (NHC) generates in situ is shown to be an efficient catalyst. Benzoin condensation also occured as side reaction.
The Direct Conversion of α-Hydroxyketones to Alkynes
Ghiringhelli, Francesca,Nattmann, Lukas,Bognar, Sabine,Van Gemmeren, Manuel
, p. 983 - 993 (2019/01/24)
Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.
