One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System

doi:10.6023/cjoc201505046

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2537-2544.DOI: 10.6023/cjoc201505046 Previous Articles Next Articles

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Au(I)配合物/锌盐催化体系中“一步法”合成2,4-二取代噻唑的研究

吴功德^a, 王晓丽^a, Liming Zhang^b, 张方^a, 刘献锋^a, 刘从容^a

a 南京工程学院环境工程学院南京 211167;
b Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA 93106, USA

收稿日期:2015-05-29 修回日期:2015-08-27 发布日期:2015-09-06
通讯作者: 王晓丽 E-mail:wangxiaoli212@njit.edu.cn
基金资助:
国家自然科学基金(Nos. 21003073, 21203093)、江苏省自然科学基金(No. BK20141388)和江苏省青蓝工程基金资助项目.

One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System

Wu Gongde^a, Wang Xiaoli^a, Zhang Liming^b, Zhang Fang^a, Liu Xianfeng^a, Liu Congrong^a

a Department of Environment and Technology, Nanjing Institute of Technology, Nanjing 211167;
b Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA 93106, USA

Received:2015-05-29 Revised:2015-08-27 Published:2015-09-06
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21003073, 21203093), the Natural Science Foundation of Jiangsu Province (No. BK20141388) and the Qing Lan Project of Jiangsu Province.

1. One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System.PDF(1110KB)

Abstract

Ten typical P,N-bidentate ligands were selected to synthesize the corresponding Au(I) complexes. The catalytic system of Au(I) complex/metal salt was employed in the catalytic oxidation of terminal alkynes with the oxidant of 8-methylquinoline N-oxide. And then 2,4-disubstituted thiazoles were synthesized from the oxidized alkynes and thioamides. It was found that the catalytic system of 5 mol% Mor-DalPhosAuCl/10 mol% Zn(NTf₂)₂ showed the optimum catalytic performance in this reaction via adjusting reaction parameters. Furthermore, ten kinds of 2,4-disubstituted thiazoles were effectively synthesized in one-step. So a simple and direct synthetic route was explored for the preparation of thiazoles and their derivatives.

Key words: Au(I) complex, 8-methylquinoline N-oxide, terminal alkyne, thioamide, thiazole

Cite this article

Wu Gongde, Wang Xiaoli, Zhang Liming, Zhang Fang, Liu Xianfeng, Liu Congrong. One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System[J]. Chin. J. Org. Chem., 2015, 35(12): 2537-2544.

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Au(I)配合物/锌盐催化体系中“一步法”合成2,4-二取代噻唑的研究

One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System

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