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Molecules 2019, 24, 182 17 of 41 Figure 5. Various ureas by CeO2/NMP system. Reprinted with permission from [92] (Copyright 2015 Elsevier Inc.). Indium-catalyzed transformations of CO2 with aliphatic and aromatic silylamines have been Polyureas containing urea linkages and connected by hydrogen bonds are a new kind of exploited by Stephan et al. [95]. The indium compound In(N(SiMe3)2)Cl2·(THF)n (THF = tetrahydrofuran) polymer. In 2016, good to excellent yields of various polyureas were achieved with different Figure 5. Various ureas by CeO2/NMP system. Reprinted with permission from [92] (Copyright 2015 was able to efficiently catalyze the reaction and afford a wide range of aryl and alkyl ureas with diamines and CO2 by hexyltributylphosphonium aminotriazole (P4,4,4,6ATriz, ATriz = Elsevier Inc.). 0.05–5 mol% catalyst loadings. Notably, the available main group metal-catalyzed transformations of 3-amino-1H-1,2,4-triazole) (1, Scheme 16) IL catalyst [96]. It was found that the catalytic performance CO2 were improved. was essentially consistent with the basicity of ILs described by Deng et al. Recently, some functional Polyureas containing urea linkages and connected by hydrogen bonds are a new kind of Polyureas containing urea linkages and connected by hydrogen bonds are a new kind of polymer. polyureas were successfully synthesized via the polymerization of CO2 with diamines using amino polymer. In 2016, good to excellent yields of various polyureas were achieved with different In 2016, good to excellent yields of various polyureas were achieved with different diamines and triazole alkali salts i.e., MATriz as catalysts (2, Scheme 16), and M was Li, Na, K [97]. More diamines and CO2 by hexyltributylphosphonium aminotriazole (P4,4,4,6ATriz, ATriz = CO by hexyltributylphosphonium aminotriazole (P ATriz, ATriz = 3-amino-1H-1,2,4-triazole) im2 portantly, the catalysts could be reused for several t4i,m4,4e,6s without obvious deactivation. 3-amino-1H-1,2,4-triazole) (1, Scheme 16) IL catalyst [96]. It was found that the catalytic performance (1, Scheme 16) IL catalyst [96]. It was found that the catalytic performance was essentially consistent Additionally, Arai et al. found that DBU (3, Scheme 16) was the most active among multiple was essentially consistent with the basicity of ILs described by Deng et al. Recently, some functional witohrgtahneibcaasnicdityinoofrIgLasndicesbcarisbeedcabtaylyDsetsnginetadl.dRiteiocnenotlfy,CsoOm2etofu4n,c7t,i1o0n-tarliopxoal-y1u,1r3e-atsriwdecraenseudciacemsisnfuelly polyureas were successfully synthesized via the polymerization of CO2 with diamines using amino syn(TthOeTsiDzDedAv)ia[9t8h]e.pDoBlyUmecroizualdtioancotifvCatOe2bwoitthdCiOam2iannedsu-sNinHg2amgrionuoptrioafzoTleOaTlDkaDliAs,alwtshi.iec.h,MwAaTsriz triazole alkali salts i.e., MATriz as catalysts (2, Scheme 16), and M was Li, Na, K [97]. More as dcaetmaloynssttsra(2te, dSchbyemine 1s6it)u, anhdigMh-pwreassuLrie, Naatt,eKnu[a9t7e]d. Mtotrael imrefpleocrtanctely,Ftohuercieartatlryasntsfcoorumldinbferarereudsed importantly, the catalysts could be reused for several times without obvious deactivation. forspsevcterroaslctoipmye(sAwTiRth-FoTuItRo),brveisoultsindgeainctaivhaitgiohnc.atalytic performance (Figure 6). Additionally, Arai et al. found that DBU (3, Scheme 16) was the most active among multiple organic and inorganic base catalysts in addition of CO2 to 4,7,10-trioxa-1,13-tridecanediamine (TOTDDA) [98]. DBU could activate both CO2 and -NH2 group of TOTDDA, which was demonstrated by in situ high-pressure attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), resulting in a high catalytic performance (Figure 6). Scheme 16. Synthesis of polyureas via the polymerization of CO2 with diamines. Scheme 16. Synthesis of polyureas via the polymerization of CO2 with diamines. Additionally, Arai et al. found that DBU (3, Scheme 16) was the most active among multiple organic and inorganic base catalysts in addition of CO2 to 4,7,10-trioxa-1,13-tridecanediamine (TOTDDA) [98]. DBU could activate both CO2 and -NH2 group of TOTDDA, which was demonstrated by in situ high-pressure attenuated total reflectance Fourier transform infrared spectroscopy Scheme 16. Synthesis of polyureas via the polymerization of CO2 with diamines. (ATR-FTIR), resulting in a high catalytic performance (Figure 6). Figure 6. (1) FTIR spectra of (a) TOTDDA, (b) DBU, and (c) mixture of TOTDDA and DBU (TOTDDA:DBU was 10:1). The protonation of DBU by TOTDDA indicated that DBU could activate the -NH2 group of TOTDDA. (2) In situ ATR-FTIR spectra of DBU (C=N) and DBU·CO2 (C=O) collected at different periods of reaction time. The new band at 1644 cm−1 is assignable to C=O and this implies the formation of the complex of DBU·CO2. Reaction conditions: DBU 2 mmol, CO2 8 MPa, 60 ◦C. Reprinted with permission from [98] (Copyright 2018 John Wiley and Sons).PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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