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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 Molecules 2019, 24, 182 MPa, 60 °C. Reprinted with permission from [98] (Copyright 2018 John Wiley and Sons). 18 of 41 2.5. Novel Synthetic Strategies of Carbamate Derivatives Based on Amines and CO2 2.5. Novel Synthetic Strategies of Carbamate Derivatives Based on Amines and CO2 2.5.1. N-Tosylhydrazones as a Building Block to Construct C-N Bond 2.5.1. N-Tosylhydrazones as a Building Block to Construct C-N Bond N-Tosylhydrazones have been extensively employed as useful building blocks to construct N-Tosylhydrazones have been extensively employed as useful building blocks to construct complicated molecules. In 2015, Jiang et al. reported the first approach for the synthesis of organic complicated molecules. In 2015, Jiang et al. reported the first approach for the synthesis of carbamates by a three-component coupling reaction of CO2, amines, and N-tosylhydrazones organic carbamates by a three-component coupling reaction of CO2, amines, and N-tosylhydrazones (Scheme 17a) [99]. Notably, in the presence of K2CO3 and a mixed CH3CN/H2O solvent, the reaction (Scheme 17a) [99]. Notably, in the presence of K2CO3 and a mixed CH3CN/H2O solvent, the reaction system tolerates a variety of valuable functional groups on the products, which provided ample system tolerates a variety of valuable functional groups on the products, which provided ample potential for further organic syntheses. Subsequently, Chung et al. modified the procedure potential for further organic syntheses. Subsequently, Chung et al. modified the procedure performed performed under mild conditions with desired carbamates (Scheme 17b) [100]. Nevertheless, poor under mild conditions with desired carbamates (Scheme 17b) [100]. Nevertheless, poor yields were yields were observed compared with Jiang’s work. observed compared with Jiang’s work. R R1 N O N NHTs (a) K2CO3, CH3CN/H2O (15:1) 120 °C, 4 MPa, 24 h, 39-87% (b) CH3NO2 80 °C, 0.1 MPa, 18 h, 38-76% O R1 + NH+CO2 R1 R2 (c) Pd(PPh3)2Cl2 (10 mol%) NaOtBu (6 equiv.) diglyme, 140 °C, 0.1 MPa, 24 h 33-76% R2 R1, R2 = H, Alkyl, Ph, Aryl; R = Cl, Br, I, H, Ph, Aryl; R O R2 HN N2 NNHTs R2 I + R3 NH2 + CO2 (d) Plausible reaction mechanism of N-tosylhydrazone, diethylamine and CO2 CO2 + H2O N NHTs K2CO3 N2 A B ON ON + CD H2CO3 R3 R1 2 Et NH O Et Et - N2 M1 +NO+ Et CO2 M2 Et Et NH2 K2CO3 OO Scheme 17. N-tosylhydrazones as a building block to construct C-N bonds. Scheme 17. N-tosylhydrazones as a building block to construct C-N bonds. At present, however, there is insufficient evidence for the proposed mechanism [99]. Presumably, for example, N-tosylhydrazone decomposes in the presence of K2CO3, and generates diazo compound, which can be followed by a protonation and a thermodynamically favorable liberation of dinitrogen to give allylic carbocation species M1 (a resonance hybrid of A and B) (Scheme 17d). Finally, the carbamate anion of M2 as a nucleophile attacks to M1 generating products of C and D.PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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