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Molecules 2019, 24, 182 Molecules 2019, 24, x FOR PEER REVIEW 31 of 41 32 of 42 Molecules 2019, 24, x FOR PEER REVIEW In 2015, Su and Wang [144] demonstrated a supported Au catalyst (Au deposited on alumina) 32 of 42 In 2015, Su and Wang [144] demonstrated a supported Au catalyst (Au deposited on alumina) In 2015, Su and Wang [144] demonstrated a supported Au catalyst (Au deposited on alumina) which was highly effective for the methylation of both aromatic and aliphatic amines using CO2/H2 which was highly effective for the methylation of both aromatic and aliphatic amines using CO2/H2 which was highly effective for the methylation of both aromatic and aliphatic amines using CO−21/H2 to N-methylated products (Scheme 35). The average TOF based on surface Au atoms was 45 h in −1 to N-methylated products (Scheme 35). The average TOF based on surface Au atoms was 45 h−1 in to N-methylated products (Scheme 35). The average TOF based on surface Au atoms was 45 h in the methylation of aniline with CO2 and H2. Moreover, in their work, a variety of amines including the methylation of aniline with CO2 and H2. Moreover, in their work, a variety of amines including the methylation of aniline with CO2 and H2. Moreover, in their work, a variety of amines including aromatic, aliphatic, secondary, and primary amines were demonstrated with good performance aromatic, aliphatic, secondary, and primary amines were demonstrated with good performance (40– aromatic, aliphatic, secondary, and primary amines were demonstrated with good performance (40– (40–99% yield). Notably, the catalytic scheme could make the one-pot method of primary amines, 99% yield). Notably, the catalytic scheme could make the one-pot method of primary amines, 99% yield). Notably, the catalytic scheme could make the one-pot method of primary amines, aldehydes, and CO2 with H2 to unsymmetrical tertiary amines. In addition, to extend the work, Du et aldehydes, and CO2 with H2 to unsymmetrical tertiary amines. In addition, to extend the work, Du et aldehydes, and CO2 with H2 to unsymmetrical tertiary amines. In addition, to extend the work, Du et al. revealed that with the decrease of the Au nanoparticle size from 8.3 to 1.8 nm, the TOF values for al. revealed that with the decrease of the Au nanoparticle size from 8.3 to 1.8 nm, the TOF values for al. revealed that with the decrease of the Au nanoparticle size from 8.3 to 1.8 nm, the TOF values for methylation of N-methylaniline with CO2/H2 increased [145]. methylation of N-methylaniline with CO2/H2 increased [145]. methylation of N-methylaniline with CO2/H2 increased [145]. 1 R1H 11 R H Au/Al2O3-VS R1 Au/Al O -VS R CH R1 CH 3 3 1N 23CH3RCH3 R1NHor N +CO2+H2 N or N RNH2or CO2+H2 or N 22 R2 2 R CHR2 One-pot mutilcomponent reaction One-pot mutilcomponent reaction 1 R1NH + R NH2 O Au/Al O -VS N Au/Al2O3-VS N OR + CO/H + CO2/H2 2222 Scheme 35. Au-catalyzed methylation of amine with CO2 and H2. Scheme 35. Au-catalyzed methylation of amine with CO2 and H2. Scheme 35. Au-catalyzed methylation of amine with CO2 and H2. Zhao et al. demonstrated that PdGa bimetallic alloy nanoparticles were highly dispersed on the Zhao et al. demonstrated that PdGa bimetallic alloy nanoparticles were highly dispersed on the Zhao et al. demonstrated that PdGa bimetallic alloy nanoparticles were highly dispersed on the TiO2 support, and the CO2 could be activated through the interaction between the electron-deficient TiO2 support, and the CO2 could be activated through the interaction between the electron-deficient TiO2 support, and the CO2 could be activated through the interaction between the electron-deficient Pd and Ga, which was confirmed by several detailed characterization studies (TEM, TPR, XPS, Pd and Ga, which was confirmed by several detailed characterization studies (TEM, TPR, XPS, Pd and Ga, which was confirmed by several detailed characterization studies (TEM, TPR, XPS, CO-adsorption IR and high-pressure in situ FTIR). The generation of a formic acid intermediate CO-adsorption IR and high-pressure in situ FTIR). The generation of a formic acid intermediate was CO-adsorption IR and high-pressure in situ FTIR). The generation of a formic acid intermediate was was proposed for the methylation (Scheme 36) [141]. As a result, 98% conversion and 94% selectivity proposed for the methylation (Scheme 36) [141]. As a result, 98% conversion and 94% selectivity for proposed for the methylation (Scheme 36) [141]. As a result, 98% con◦version and 94% selectivity for for N-methylaniline was obtained under the identical conditions (180 C, 5 MPa H2, 5 MPa CO2, 10 h). N-methylaniline was obtained under the identical conditions (180 °C, 5 MPa H2, 5 MPa CO2, 10 h). N-methylaniline was obtained under the identical conditions (180 °C, 5 MPa H2, 5 MPa CO2, 10 h). Scheme 36. Reaction route of PdGa-catalyzed methylation of N-methylaniline [141]. Scheme 36. Reaction route of PdGa-catalyzed methylation of N-methylaniline [141]. Scheme 36. Reaction route of PdGa-catalyzed methylation of N-methylaniline [141]. CH3 R 3 Possible mechanism Possible mechanism HH HH NH NH N NH N NH2 NH N NH N 2 Au Cat. Au Cat. Au Cat. Au Cat. Au Cat. Au Cat. Au Cat. Au Cat. CO/H OH CO/H OH H2 CO2 /H2 O 222222 CO2 /H2 O H2 1 R1 R2 H RH R2 R 2 The reductive N-formylation of amines using CO2 and hydrogen is also a promising means The reductive N-formylation of amines using CO2 and hydrogen is also a promising means of The reductive N-formylation of amines using CO2 and hydrogen is also a promising means of of fixing CO2 into value-added chemicals, and heterogeneous catalysis schemes were also well fixing CO2 into value-added chemicals, and heterogeneous catalysis schemes were also well fixing CO2 into value-added chemicals, and heterogeneous catalysis schemes were also well developed recently (Table 5). Lately, the Shi group were the first to report a highly active developed recently (Table 5). Lately, the Shi group were the first to report a highly active supported developed recently (Table 5). Lately, the Shi group were the first to report a highly active supported supported palladium nanoparticle catalyst for the N-formylation of various aliphatic amines with palladium nanoparticle catalyst for the N-formylation of various aliphatic amines with CO2 and H2 palladium nanoparticle catalyst for the N-formylation of various aliphatic amines with CO2 and H2 CO2 and H2 (Scheme 37) [147]. During the preparation, Pd(NH3)xCly was initially adsorbed onto (Scheme 37) [147]. During the preparation, Pd(NH3)xCly was initially adsorbed onto the carbon (Scheme 37) [147]. During the preparation, Pd(NH3)xCly was initially adsorbed onto the carbon the carbon support, and then the active nano-Pd particles were generated by in situ reduction. support, and then the active nano-Pd particles were generated by in situ reduction. Additionally, the support, and then the active nano-Pd particles were generated by in situ reduction. Additionally, the Additionally, the activity of the Pd/C catalysts can be tuned by -OH groups through modulating activity of the Pd/C catalysts can be tuned by -OH groups through modulating the activity of the Pd/C catalysts can be tuned by -OH groups through modulating the the hydrophilic/hydrophobic properties of the carbon surface which further potentially promote the hydrophilic/hydrophobic properties of the carbon surface which further potentially promote the hydrophilic/hydrophobic properties of the carbon surface which further potentially promote the adsorption of CO2 and amines near the Pd sites. adsorption of CO2 and amines near the Pd sites. adsorption of CO2 and amines near the Pd sites.PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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