4.8 Article

Ionic Liquid-Catalyzed C-S Bond Construction using CO2 as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles

Journal

ACS CATALYSIS
Volume 5, Issue 11, Pages 6648-6652

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b01874

Keywords

carbon dioxide; ionic liquid; organosulfur compounds; room temperature; conversion

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The construction of the C-S bond using CO, as a c1 feedstock of S-containing compounds and is of great significance. Herein, we report the acetate-based ionic liquids (ILs)-catalyzed synthesis of benzothiazoles via cyclization of 2-aminothiophenols with CO2 and hydrosilane under mild conditions (e.g., 60 degrees C, 0.5 MPa). It was found that the IL (e.g., 1-butyl-3-methylimidazolium acetate, [Bmim][OAc]) served as a multifunctional catalyst with activating CO2 and hydrosilane to form a formoxysilane intermediate, as well as simultaneously activating 2-aminothiophenols through a hydrogen bond, finally resulting in the production of benzothiazoles. [Bmim][OAc] showed the best performance, and a series of benzothiazoles were obtained in high yields. To the best of our knowledge, this is the first protocol for the synthesis of benzothiazoles using CO2 as a Cl building block under metal-free and mild conditions.

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