AgI /TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones
Autor: | Xue-Dong Li, Yao Chang, Liang-Nian He, Xian-Dong Lang, Qing-Wen Song |
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Rok vydání: | 2017 |
Předmět: |
Green chemistry
010405 organic chemistry Hydrogen bond Homogeneous catalysis Propargyl alcohol 010402 general chemistry 01 natural sciences Atomic and Molecular Physics and Optics 0104 chemical sciences Turnover number chemistry.chemical_compound Cascade reaction chemistry Carbon dioxide Propargyl Organic chemistry Physical and Theoretical Chemistry |
Zdroj: | ChemPhysChem. 18:3182-3188 |
ISSN: | 1439-4235 |
Popis: | 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 Ag2 O/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 . |
Databáze: | OpenAIRE |
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