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Thermodynamically favorable protocol for the synthesis of 2-oxazolidinones via Cu(I)-catalyzed three-component reaction of propargylic alcohols, CO2 and 2-aminoethanols
Journal of CO2 Utilization ( IF 7.7 ) Pub Date : 2018-02-24 , DOI: 10.1016/j.jcou.2018.01.022
Xue-Dong Li , Yu Cao , Ran Ma , Liang-Nian He

Efficient CuI/1,10-phen-catalyzed three-component cascade reaction of propargylic alcohols, CO2, and 2-aminoethanols has been firstly developed for the thermodynamically favourable preparation of 2-oxazolidinones. In the presence of commercially available CuI, 1,10-phen (1,10-phenanthroline) and t-BuOK, the cascade reaction afforded the desired products in good to excellent yields with a broad substrate scope (14 examples). The predicted copper complex Cu2I2(phen)2 in situ formed from CuI and 1,10-phen could activate the triple bond through coordination. The isolation of α-alkylidene cyclic carbonate as the reaction intermediate suggests that the carboxylative cyclization of propargylic alcohol with CO2, followed by ring-opening reaction, is involved in the one-pot three-component cascade reaction.



中文翻译:

通过Cu(I)催化的炔丙醇,CO 2和2-氨基乙醇的三组分反应合成2-恶唑烷酮的热力学上有利的协议

丙醇,CO 2和2-氨基乙醇的高效CuI / 1,10-phen催化的三组分级联反应已被开发出来,用于热力学上有利的2-恶唑烷酮的制备。在可商购获得的CuI,1,10-吩(1,10-菲咯啉)和t - BuOK的存在下,级联反应以良好的产率和优异的产率提供了所需的产物,具有宽的底物范围(14个实施例)。原位预测的铜络合物Cu 2 I 2(phen)2 由CuI和1,10-phen形成的化合物可以通过配位激活三键。分离作为反应中间体的α-亚烷基环状碳酸酯表明,一锅三组分级联反应涉及炔丙醇与CO 2的羧基环化,然后开环反应。

更新日期:2018-02-24
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