Catalytic Conversion of Carbon Dioxide through C-N Bond

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molecules Review Catalytic Conversion of Carbon Dioxide through C-N Bond Formation Jing-Yuan Li, Qing-Wen Song * , Kan Zhang and Ping Liu State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China; (J.-Y.L.); (K.Z.); (P.L.) *;Tel.:+86-0351-4250105 Received: 1 December 2018; Accepted: 4 January 2019; Published: 5 January 2019 􏰁􏰂􏰃 􏰅􏰆􏰇 􏰈􏰉􏰊􏰋􏰌􏰂􏰍 Abstract: From the viewpoint of green chemistry and sustainable development, it is of great significance to synthesize chemicals from CO2 as C1 source through C-N bond formation. During the past several decade years, many studies on C-N bond formation reaction were involved, and many efforts have been made on the theory. Nevertheless, several great challenges such as thermodynamic limitation, low catalytic efficiency and selectivity, and high pressure etc. are still suffered. Herein, recent advances are highlighted on the development of catalytic methods for chemical fixation of CO2 to various chemicals through C-N bond formation. Meanwhile, the catalytic systems (metal and metal-free catalysis), strategies and catalytic mechanism are summarized and discussed in detail. Besides, this review also covers some novel synthetic strategies to urethanes based on amines and CO2. Finally, the regulatory strategies on functionalization of CO2 for N-methylation/N-formylation of amines with phenylsilane and heterogeneous catalysis N-methylation of amines with CO2 and H2 are emphasized. Keywords: carbon dioxide utilization; chemicals; C-N bond formation; hydrogenation; reaction mechanism; synthetic methods 1. Introduction With the development of green chemistry, sustainable raw materials are urgently required, and growing attention is being paid to green resources such as biomass [1], carbon dioxide (CO2) [2–4] etc. due to their good features such as abundance, renewability and sustainability. In the past several decades, utilization of CO2 as an ideal C1 building block become a hot and promising field in both academic and industrial respects. A large number of advantages promoted the wide and deep research on catalytic conversion of CO2 into chemicals (C-O, C-N and C-C bond construction) and fuels [5–7]. Though great breakthroughs have been achieved during these years, however, CO2 conversion still faces many challenges due to its thermodynamic stability and kinetic inertness. Therefore, many strategies have been employed for effective CO2 conversion, including CO2 and substrate activation and active reagents (such as hydrogen, alkene, alkyne, epoxides, amines, etc.) [8–11] with high free-energy. Among the active substrates, amines were demonstrated to be some of the most high-efficiency candidates for chemical fixation of CO2 through C-N bond formation. The earliest and most successful example is the production of urea from ammonia and CO2, which accounts for most (>90%) of all of the industrial chemicals produced using CO2 as a chemical feedstock so far. Besides, many other N-contained chemicals such as urea derivatives, carbamates, oxazolinones, quinazoline-2,4(1H,3H)-diones, formamides, methylamines, etc. could also be synthesized through C-N bond formation from CO2 and various amines or their derivatives [9]. In 2011, the He group comprehensively reviewed the development of CO2 conversion through C-N bond formation with the production of oxazolidinones, quinazolines, carbamates, isocyanates and Molecules 2019, 24, 182; doi:10.3390/molecules24010182

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