Abstract
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% 1,5,7-triazabicylo[4.4.0]dec-5-ene ([TBDH][TFE]) trifluoroethanol was found to be able to synergistically activate the substrate and CO2, thus catalyzing this cascade reaction under atmospheric CO2 pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 °C.
Highlights
The accumulation of CO2 in atmosphere has aroused considerable concern due to its link to the climate change; effective strategies are urgently needed to mitigate the increasing CO2 buildup [1,2,3]
Oxazolidinones, which are in the family of carbamates, are important chiral auxiliaries in organic synthesis [31,32] and are common structural units in drugs [33,34] and agrochemicals [35]
Synthesis of 2-oxazolidinones using CO2 and appropriate substrates has attracted much attention [14,39,40], among which the direct synthesis of oxazolidinones starting from 2-aminoethanols and CO2 is considered as an ideal route because the aqueous amino alcohols have been widely utilized to capture
Summary
The accumulation of CO2 in atmosphere has aroused considerable concern due to its link to the climate change; effective strategies are urgently needed to mitigate the increasing CO2 buildup [1,2,3]. Oxazolidinones, which are in the family of carbamates, are important chiral auxiliaries in organic synthesis [31,32] and are common structural units in drugs [33,34] and agrochemicals [35]. Gabriele et al reported an alternative unconventional synthetic method to produce oxazolidinones starting from 2-amino alcohols with CO in ionic liquids [38]. Synthesis of 2-oxazolidinones using CO2 and appropriate substrates has attracted much attention [14,39,40], among which the direct synthesis of oxazolidinones starting from 2-aminoethanols and CO2 is considered as an ideal route because the aqueous amino alcohols have been widely utilized to capture
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