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
收稿日期: 2015-05-29
修回日期: 2015-08-27
网络出版日期: 2015-09-06
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
Received date: 2015-05-29
Revised date: 2015-08-27
Online 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.
选用了10种典型的P,N-双齿配体并合成相应的Au(I)配合物; 以8-甲基喹啉-氮氧化物为氧化剂, Au(I)配合物/金属盐为催化剂, 在氧化端炔与硫代酰胺反应制备2,4-二取代噻唑的反应中, 考察了不同的金属盐对催化剂性能的影响, 优化了反应参数; 结果表明, 5 mol% Mor-DalPhosAuCl/10 mol% Zn(NTf2)2催化体系在该反应中显示出了较高的催化活性, 且"一步法"高效地合成了10种2,4-二取代噻唑化合物, 为噻唑及其衍生物的制备探索出了一条简便直接的合成路线.
关键词： Au(I)配合物; 8-甲基喹啉-氮氧化物; 端炔; 硫代酰胺; 噻唑
吴功德 , 王晓丽 , Liming Zhang , 张方 , 刘献锋 , 刘从容 . 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[J]. 有机化学, 2015 , 35(12) : 2537 -2544 . DOI: 10.6023/cjoc201505046
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
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