77387-64-5Relevant articles and documents
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.]
Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
Meitinger, Nicolas,Mengele, Alexander K.,Witas, Kamil,Kupfer, Stephan,Rau, Sven,Nauroozi, Djawed
, p. 6555 - 6562 (2020/10/02)
The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.
Unexpected transformation of aldehydes into benzoins with Copper(I)/Samarium
Liu, Yongjun,Wang, Hui,Fu, Yulong,Qi, Yan,Yang, Kuiwei
, p. 259 - 266 (2013/12/04)
The reductive coupling of aldehydes to afford pinacolic alcohols using all kinds of reducing agents involving samarium is well known. In this report, however, treatment of aromatic aldehydes with Cu(I)/Sm system produces benoins and/or benzils in good yields. A possible mechanism is proposed where Cu(I) not only activates the Sm metal but also promotes the dehydrogenation of the intermediates, during which a Cu(III) species may be involved. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]