Ag I /TMG‐Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2‐Aminoethanols to 2‐Oxazolidinones
In: ChemPhysChem, Jg. 18 (2017), Heft 22, S. 3182-3188
academicJournal
Zugriff:
Chemical valorization of CO 2 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, CO 2 , and 2‐aminoethanols was developed for the synthesis of 2‐oxazolidinones and an equal amount of α‐hydroxyl ketones promoted by Ag 2 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/CO 2 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 CO 2 .
Titel: |
Ag I /TMG‐Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2‐Aminoethanols to 2‐Oxazolidinones
|
---|---|
Autor/in / Beteiligte Person: | Li, Xue‐Dong ; Song, Qing‐Wen ; Lang, Xian‐Dong ; Chang, Yao ; He, Liang‐Nian ; National Natural Science Foundation of China |
Link: | |
Zeitschrift: | ChemPhysChem, Jg. 18 (2017), Heft 22, S. 3182-3188 |
Veröffentlichung: | Wiley, 2017 |
Medientyp: | academicJournal |
ISSN: | 1439-4235 |
DOI: | 10.1002/cphc.201700297 |
Schlagwort: |
|
Sonstiges: |
|