Data for the synthesis of β-oxopropylcarbamates from propargylic alcohols, secondary amines and CO2 catalyzed by a recyclable AgBr/ionic liquid system under ambient pressure

Dandan Song,Di Li,Xuan Xiao,Cheng Chen,Somboon Chaemchuen,Ye Yuan,Francis Verpoort

doi:10.1016/j.dib.2018.08.183

Dandan Song, Di Li + Show 5 more

Open Access

https://doi.org/10.1016/j.dib.2018.08.183

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Abstract

Data presented here are related with the research article entitled “Synthesis of ß -oxopropylcarbamates in a recyclable AgBr/ionic liquid catalytic system: An efficient assembly of CO2 under ambient pressure” (Song et al., 2018) [1]. In this data article, the general synthetic procedures of ß-oxopropylcarbamates through the three-component reaction of propargylic alcohols, secondary amines and carbon dioxide (CO2) catalyzed by a recyclable AgBr/ionic liquid (IL) system under mild pressure are described. Furthermore, the process for recycling the catalysts is supplied as well. Specifically, the investigative data for the temperature, amount of ILs, reaction time as well as the state of silver in the system are also reported. Finally, all the target products are confirmed by 1H NMR, 13C NMR, and high-resolution mass spectroscopy (HR-MS).

Highlights

Data presented here are related with the research article entitled “Synthesis of ß -oxopropylcarbamates in a recyclable AgBr/ionic liquid catalytic system: An efficient assembly of CO2 under ambient pressure” (Song et al, 2018) [1]
The procedures for the synthesis of ß-oxopropylcarbamates and the process for recycling the catalysts could be followed by other researchers
1.62 mmol a Reaction conditions: AgBr (0.05 mmol), 2-methylbut-3-yn-2-ol (5 mmol), pyrolidine (5 mmol), CO2 (0.1 MPa), 45 °C, 8 h. b Yields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as the internal standard

Summary

General information

1.62 mmol a Reaction conditions: AgBr (0.05 mmol), 2-methylbut-3-yn-2-ol (5 mmol), pyrolidine (5 mmol), CO2 (0.1 MPa), 45 °C, 8 h. b Yields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as the internal standard. 1.62 mmol a Reaction conditions: AgBr (0.05 mmol), 2-methylbut-3-yn-2-ol (5 mmol), pyrolidine (5 mmol), CO2 (0.1 MPa), 45 °C, 8 h. %-Yieldb a Reaction conditions: AgBr (0.05 mmol), [C2C1im][OAc] (1.25 mmol), 2-methylbut-3-yn-2-ol (5 mmol), pyrolidine (5 mmol), CO2 (0.1 MPa), 8 h. B Yields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as the internal standard. 99 a Reaction conditions: AgBr (0.05 mmol), [C2C1im][OAc] (1.25 mmol), 2-methylbut-3-yn-2-ol (5 mmol), pyrolidine (5 mmol), CO2 (0.1 MPa), 45 °C. b Yields were determined by 1H NMR spectroscopy using. 13C NMR for detection of the existence of carbene-Ag complex. Chemical shifts (δ) and coupling constants (J) are given in ppm and hertz (Hz), respectively. HR-MS was recorded on a Bruker Daltonics microTOF-QII mass spectrometer

The structures of ionic liquids

Effects of temperature and time on the coupling reaction

Findings

Procedure for the recycling experiment