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Molecules 2019, 24, 182 11 of 41 Molecules 2019, 24, x FOR PEER REVIEW 11 of 42 Hence, organic bases, electrophiles and CeO2 were used for removing water from the system in most bases, electrophiles and CeO2 were used for removing water from the system in most cases to improve cases to improve the yield of products [65,66]. the yield of products [65,66]. In 2018, Repo et al. developed an efficient one-pot approach using an external base and In 2018, Repo et al. developed an efficient one-pot approach using an external base and p-toluenesulfonyl chloride (TsCl) as a hydroxyl group activating reagent to synthesize cyclic p-toluenesulfonyl chloride (TsCl) as a hydroxyl group activating reagent to synthesize cyclic carbamates carbamates from CO2 and amino alcohols (Scheme 9b) [67]. This stoichiometric reaction system from CO2 and amino alcohols (Scheme 9b) [67]. This stoichiometric reaction system allowed allowed 2-oxazolidinones with the 3-aryl-5-alkyl substitution pattern to be obtained under mild 2-oxazolidinones with the 3-aryl-5-alkyl substitution pattern to be obtained under mild conditions conditions in good yields and high enantiomeric excess. In the reaction (Scheme 9c), a carbamate salt in good yields and high enantiomeric excess. In the reaction (Scheme 9c), a carbamate salt is formed is formed from CO2 and amino alcohol, followed by the tosylation of the -OH to improve its leaving from CO2 and amino alcohol, followed by the tosylation of the -OH to improve its leaving group group character. Finally, ideal product is obtained via a ring-closing process. However, the character. Finally, ideal product is obtained via a ring-closing process. However, the carbamate species carbamate species must be formed firstly and stabilized to avoid the competition of N-tosylation must be formed firstly and stabilized to avoid the competition of N-tosylation reaction. Unlike the reaction. Unlike the above base-promoted work, a series of K-La-MgO with different K loadings (1, above base-promoted work, a series of K-La-MgO with different K loadings (1, 3, 5, and 7 wt%) 3, 5, and 7 wt%) synthesized by combustion were screened for carbonylation of diethanolamine in a synthesized by combustion were screened for carbonylation of diethanolamine in a green and clean green and clean route [68]. Among them, 5% K-La-MgO was found to show the best performance. route [68]. Among them, 5% K-La-MgO was found to show the best performance. The catalytic The catalytic process with 5% K-La-MgO offered 72% conversion of diethanol amine and 100% process with 5% K-La-MgO offered 72% conversion of diethanol amine and 100% selectivity of selectivity of 3-(2-hydroxyethyl)-1,3-oxazolidin◦-2-one at 150 °C and 2.0 MPa CO2 pressure. 3-(2-hydroxyethyl)-1,3-oxazolidin-2-one at 150 C and 2.0 MPa CO2 pressure. Scheme 9. Synthesis of 2-oxazolidinones through carbonylation of amino alcohols with CO2. Additionally, a thermodynamically favourable one-pot three-component approach of propargylic Additionally, a thermodynamically favourable one-pot three-component approach of alcohols,CO and2-aminoethanolswasdescribedbyHeetal.in2016atfirst,offering2-oxazolidinones propargylic a2 lcohols, CO2 and 2-aminoethanols was described by He et al. in 2016 at first, offering with equal amount of α-hydroxyl ketone (Scheme 10a). As shown in Table 2, organic solvent, high 2-oxazolidinones with equal amount of α-hydroxyl ketone (Scheme 10a). As shown in Table 2, CO pressureandexcesspropargylicalcoholswereindispensableintheAg-basedcatalyticsystemto orga2nic solvent, high CO2 pressure and excess propargylic alcohols were indispensable in the achieve excellent yields [69,70], while in the CuI/1,10-phen-catalyzed three-component reaction, the Ag-based catalytic system to achieve excellent yields [69,70], while in the CuI/1,10-phen-catalyzed desired products in good to excellent yields were obtained under mild reaction conditions without three-component reaction, the desired products in good to excellent yields were obtained under solvent. It was worth mentioning that cheap, commercially available copper catalysts, and the ability mild reaction conditions without solvent. It was worth mentioning that cheap, commercially of C≡C activation have been widely utilized in CO transformations. The reaction consists of two available copper catalysts, and the ability of C≡C2activation have been widely utilized in CO2 steps. Firstly, α-alkylidene cyclic carbonate intermediate M1 is formed via the carboxylative cyclization transformations. The reaction consists of two steps. Firstly, α-alkylidene cyclic carbonate of propargylic alcohol and CO . Then, M1 undertakes a nucleophilic addition by a 2-aminoalcohol intermediate M1 is formed via2the carboxylative cyclization of propargylic alcohol and CO2. Then, to form the corresponding β-oxopropylcarbamate species M2, which simultaneously affords the M1 undertakes a nucleophilic addition by a 2-aminoalcohol to form the corresponding β-oxopropylcarbamate species M2, which simultaneously affords the 2-oxazolidinone and an α-hydroxyketone with a subsequent intramolecular cyclization (Scheme 10b). Notably, copperPDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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