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Molecules 2019, 24, x FOR PEER REVIEW 13 of 42 Molecules 2019, 24, 182 13 of 41 an environmentally benign process with 100% atom efficiency. This reaction was highlighted by Soleimani-Amiri et al [72]. They classified the reactions based on the type of catalysts to review the works before 2017. Thus, we continued to summarise the published work in recent two years. According to the previous literature [73–75], amino group of 2-aminobenzonitrile is initially According to the previous literature [73–75], amino group of 2-aminobenzonitrile is initially activated by basic catalysts, which facilitates the nucleophilic attack of 2-aminobenzonitrile at CO2 activated by basic catalysts, which facilitates the nucleophilic attack of 2-aminobenzonitrile at CO2 to to generate intermediate A. Then, nucleophilic cyclization of A produces B. Finally, B converts into generate intermediate A. Then, nucleophilic cyclization of A produces B. Finally, B converts into quinazoline-2,4(1H,3H)-dione with the regeneration of the catalysts (Scheme 11). quinazoline-2,4(1H,3H)-dione with the regeneration of the catalysts (Scheme 11). NH2 base CN CO2 H N O CN base NH C O N C O- H+ C N N- OH base NH H O O H O O O Undeniably, numerous IL-based systems [73,74,76–78] exhibit excellent performance in the Dyson’s work [80] and Wang’s work [81] was published (Scheme 12). A N H+ B Scheme 11. Possible reaction pathway of 2-aminobenzonitrile and CO2. Scheme 11. Possible reaction pathway of 2-aminobenzonitrile and CO2. Undeniably, numerous IL-based systems [73,74,76–78] exhibit excellent performance in the transformation of 2-aminobenzonitrile and CO2 [79]. However, almost all the reported IL systems transformation of 2-aminobenzonitrile and CO2 [79]. However, almost all the reported IL systems involve high usage amounts of dual catalyst-solvent media (>1.0 equiv.). There were no intensive and involve high usage amounts of dual catalyst-solvent media (>1.0 equiv.). There were no intensive systematic research figuring out the role of the IL, such as the effects of cation and anion until Dyson’s and systematic research figuring out the role of the IL, such as the effects of cation and anion until work [80] and Wang’s work [81] was published (Scheme 12). Scheme 12. IL-catalyzed transformation of 2-aminobenzonitrile and CO2. Scheme 12. IL-catalyzed transformation of 2-aminobenzonitrile and CO2. Dyson et al. found that the cation from the IL did not play a direct role in the activation of Dyson et al. found that the cation from the IL did not play a direct role in the activation of 2-aminobenzonitrile, CO2, or the intermediates in the catalytic cycle [80]. On the contrary, the 2-aminobenzonitrile, CO2, or the intermediates in the catalytic cycle [80]. On the contrary, the basicity of the anion had an inseparable relationship with the reaction rate. Notably, the acidity basicity of the anion had an inseparable relationship with the reaction rate. Notably, the acidity of of quinazoline-2,4(1H,3H)-dione resulted in its deprotonation in basic catalytic conditions with the quinazoline-2,4(1H,3H)-dione resulted in its deprotonation in basic catalytic conditions with the formation of quinazolide anion. Furthermore, the reaction was limited due to the neutralization of the formation of quinazolide anion. Furthermore, the reaction was limited due to the neutralization of basic IL catalyst and quinazolide anion. the basic IL catalyst and quinazolide anion. On the other hand, according to quantum-chemical calculations, NMR spectroscopic On the other hand, according to quantum-chemical calculations, NMR spectroscopic investigations and controlled experiments, Wang et al. proposed that the basicity of cation affects investigations and controlled experiments, Wang et al. proposed that the basicity of cation affects the the catalytic activity of ILs dramatically (Figure 4) [81]. In addition, the cation with more OH groups catalytic activity of ILs dramatically (Figure 4) [81]. In addition, the cation with more OH groups exhibited poorer catalytic activity. Therefore, a hydroxyl functionalized aprotic IL [Ch][Im] was exhibited poorer catalytic activity. Therefore, a hydroxyl functionalized aprotic IL [Ch][Im] was designed and exhibited high catalytic activity (Scheme 13b). designed and exhibited high catalytic activity (Scheme 13b).PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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