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Molecules 2019, 24, x FOR PEER REVIEW 10 of 42 Molecules 2019, 24, 182 10 of 41 2-oxazolidinone synthesis. It could be ascribed to the better activation of CO2 in the presence of [H3-nCYA]n− (n = 1−3) than that of [Phth]− and [2-PyO]− anions (Scheme 8e). Besides, triethanolamine (TEOA) as a low-cost and biodegradable alkanolamine showed excellent performance on affording (TEOA) as a low-cost and biodegradable alkanolamine showed excellent performance on affording 2-oxazolidinones (Scheme 8d) [59]. As can be seen from Scheme 8f, TEOA activated CO2 to form a 2-oxazolidinones (Scheme 8d) [59]. As can be seen from Scheme 8f, TEOA activated CO2 to form a ring-shaped carbonate intermediate, which could be beneficial to the reaction procedure. ring-shaped carbonate intermediate, which could be beneficial to the reaction procedure. Scheme 8. Synthesis of 2-oxazolidinones by metal-free catalytic systems. It is worth mentioning that allylamines are less active than propargyl amines in the reaction It is worth mentioning that allylamines are less active than propargyl amines in the reaction with CO because C≡C bonds are more prone to being attacked by carbamates than C=C bonds. with CO2 because C≡C bonds are more prone to being attacked by carbamates than C=C bonds. However,thecarboxylativecyclizationofallylaminesandCO wouldsignificantlyexpandthetoolbox However, the carboxylative cyclization of allylamines and2 CO2 would significantly expand the of 2-oxazolidinones synthesis. Most recently, Yu and co-workers summarized recent progress on this toolbox of 2-oxazolidinones synthesis. Most recently, Yu and co-workers summarized recent reaction by homogeneous catalysis in detail [60]. In addition, they also reviewed various cyclization progress on this reaction by homogeneous catalysis in detail [60]. In addition, they also reviewed reactions of allenic amines with CO . various cyclization reactions of allen2ic amines with CO2. 2.2.2. Direct/Indirect Condensation of Amino Alcohols and Carbon Dioxide 2.2.2. Direct/Indirect Condensation of Amino Alcohols and Carbon Dioxide In 2013, there were two excellent reviews dealing with the synthesis of 2-oxazolidinones In 2013, there were two excellent reviews dealing with the synthesis of 2-oxazolidinones through carbonylation of corresponding amino alcohols with CO2 (before 2013) by Pulla’s [14] and through carbonylation of corresponding amino alcohols with CO2 (before 2013) by Pulla’s [14] and Tomishige’s [15] groups. Recently, Fekri et al. provided a review of recent developments (before 2017) Tomishige’s [15] groups. Recently, Fekri et al. provided a review of recent developments (before in the synthesis of 2-oxazolidinone derivatives via dehydrative condensation of β-amino alcohols and 2017) in the synthesis of 2-oxazolidinone derivatives via dehydrative condensation of β-amino CO2 with a discussion on the mechanistic aspects of the reactions in detail [61]. Based on the above alcohols and CO2 with a discussion on the mechanistic aspects of the reactions in detail [61]. Based works, this review will briefly discuss only the most recent literature (2017–2018) on direct/indirect on the above works, this review will briefly discuss only the most recent literature (2017–2018) on condensation of amino alcohols and CO2. direct/indirect condensation of amino alcohols and CO2. Despite efficient processes, the direct condensation of amino alcohols and CO2 were limited by Despite efficient processes, the direct condensation of amino alcohols and CO2 were limited by harsh conditions (high temperature and pressure) and side reactions [62–64]. This could be attributed harsh conditions (high temperature and pressure) and side reactions [62–64]. This could be to the thermodynamic limitation of the reaction with water as by-product (Scheme 9a). Hence, organic attributed to the thermodynamic limitation of the reaction with water as by-product (Scheme 9a).PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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