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

被引：111

作者：

Gao, Xiang ^{[1
]}

Yu, Bo ^{[1
]}

Yang, Zhenzhen ^{[1
]}

Zhao, Yanfei ^{[1
]}

Zhang, Honge ^{[1
]}

Hao, Leiduan ^{[1
]}

Han, Buxing ^{[1
]}

Liu, Zhimin ^{[1
]}

机构：

[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Key Lab Colloid Interface & Thermodynam, Beijing 100190, Peoples R China

来源：

ACS CATALYSIS | 2015年 / 5卷 / 11期

关键词：

carbon dioxide; ionic liquid; organosulfur compounds; room temperature; conversion; CARBON-DIOXIDE; SUBSTITUTED BENZOTHIAZOLES; 3-COMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; TRANSFORMATION; FORMYLATION; METHANOL; AMINES; 2-AMINOBENZENETHIOLS; FUNCTIONALIZATION;

D O I：

10.1021/acscatal.5b01874

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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.

引用

页码：6648 / 6652

页数：5

共 45 条

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