3-Bromo-1,1,1-trifluoro-2-propanol assisted chemical fixation of CO2 and epoxides

[Display omitted] •3-Bromo-1,1,1-trifluoro-2-propanol was proved to be an excellent hydrogen-bonding donor for CO2 transformation.•Synergistic effects of hydroxyl group and iodide anion render the reaction performing at 0.5 MPa CO2.•The reaction could be carried out under solvent- and metal-free con...

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Veröffentlicht in:Tetrahedron letters 2020-03, Vol.61 (11), p.151593, Article 151593
Hauptverfasser: Ma, Hui, Zeng, Ji-jun, Tu, Dong-huai, Mao, Wei, Zhao, Bo, Wang, Kuan, Liu, Zhao-tie, Lu, Jian
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Sprache:eng
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Zusammenfassung:[Display omitted] •3-Bromo-1,1,1-trifluoro-2-propanol was proved to be an excellent hydrogen-bonding donor for CO2 transformation.•Synergistic effects of hydroxyl group and iodide anion render the reaction performing at 0.5 MPa CO2.•The reaction could be carried out under solvent- and metal-free conditions.•A broad scope of cyclic carbonates could be obtained in high yield. 3-Bromo-1,1,1-trifluoro-2-propanol (3-BTFP) in combination with n-butylammonium iodide (TBAI) was proved to be an efficient organocatalyst for chemical fixation of CO2 with various epoxides to the respective cyclic carbonates. A possible reaction mechanism was proposed wherein 3-BTFP activated epoxide through hydrogen bonding interaction. This mechanism is revealed by the results of FT-IR spectra and 1H NMR titration, and the synergetic effect functioned by 3-BTFP and TBAI ensures the reaction proceeding effectively. Herein, 3-BTFP represents a commercially available, stable and metal-free hydrogen-bonding donor for CO2 transformation, which has a potential application for the large-scale synthesis of cyclic carbonates.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151593