6317-28-8Relevant academic research and scientific papers
An efficient and recyclable AgNO3/ionic liquid system catalyzed atmospheric CO2 utilization: Simultaneous synthesis of 2-oxazolidinones and α-hydroxyl ketones
Bu, Chao,Chaemchuen, Somboon,Chen, Cheng,Du, Minchen,Gong, Yanyan,Hu, Jia,Verpoort, Francis,Yuan, Ye,Zhang, Yongxing
, p. 70 - 82 (2020/12/21)
Oxazolidinones and α-hydroxyl ketones are two series of fine chemicals that have been generally utilized in biological, pharmaceutical, and synthetic chemistry. Herein, a AgNO3/ionic liquid (IL) catalytic system was developed for the simultaneous synthesis of these compounds through the atom-economical three-component reactions of propargyl alcohols, 2-aminoethanols, and CO2. Notably, this system behaved excellent catalytic activity with the lowermost metal loading of 0.25 mol%. Meanwhile, it is the first reported metal-catalyzed system that could efficiently work under atmospheric CO2 pressure and be recycled at least five times. Evaluation of the green metrics proved the AgNO3/IL-catalyzed processes to be relatively more sustainable and greener than the other Ag-catalyzed examples. Further mechanistic investigations revealed the derivative active species of N-heterocyclic carbene (NHC) silver complexes and CO2 adducts generated during the process. Subsequently, their reactivity in this reaction was assessed for the first time, which was finally identified as beneficial for the catalytic activity.
AgI/TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones
Li, Xue-Dong,Song, Qing-Wen,Lang, Xian-Dong,Chang, Yao,He, Liang-Nian
, p. 3182 - 3188 (2017/10/03)
Chemical valorization of CO2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO2, and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag2O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO2.
Thermodynamically favorable synthesis of 2-oxazolidinones through silver-catalyzed reaction of propargylic alcohols, CO2, and 2-aminoethanols
Song, Qing-Wen,Zhou, Zhi-Hua,Wang, Mei-Yan,Zhang, Kan,Liu, Ping,Xun, Jia-Yao,He, Liang-Nian
, p. 2054 - 2058 (2017/07/25)
Development of catalytic routes to incorporate CO2 into carbonyl compounds at mild conditions remains attractive and challenging. Herein, a one-pot three-component cascade reaction of terminal propargylic alcohols, CO2, and 2-aminoethanols through AgI-based catalysis is reported for the synthesis of carbonyl compounds through C—O/C—N bond formation. This thermodynamically favorable route can be ingeniously regulated to afford a wide range of 2-oxazolidinones along with concurrent production of α-hydroxyl ketone derivatives in excellent yields and selectivity. Preliminary mechanistic studies indicate that such a process proceeds through successive formation of α-alkylidene cyclic carbonate, β-oxopropylcarbamate, and 2-oxazolidinones.
