Atmospheric Pressure of CO2 as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes
Atmospheric Pressure of CO2 as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin-2-ones with Carbamate Salts, Aldehydes and Alkynes
复制标题
常压 CO2 作为保护剂和反应物：氨基甲酸盐、醛和炔烃高效合成恶唑烷-2-酮
DOI：
10.1002/adsc.201500921
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发表时间：
2016
影响因子：
5.4
通讯作者：
Hu Chang-Wen
中科院分区：
文献类型：
--
作者：
Yu Bing;Cheng Bin-Bin;Liu Wei-Qi;Li Wei;Wang Shan-Shan;Cao Jie;Hu Chang-Wen
近年来，二氧化碳作为一种环境友好的有机合成碳源得到了广泛的应用。伯胺对二氧化碳的捕获很容易提供相应的氨基甲酸盐。本文介绍了氨基甲酸酯盐类与芳香醛和芳香族末端炔反应合成恶唑烷-2-酮的有效反应物。以5 摩尔%的CuI为催化剂，以68-91%的产率合成了不同官能团的恶唑烷-2-酮。结果表明，碘化物的协同作用对转化起重要作用。值得注意的是，捕获的二氧化碳不仅作为富含电子的伯胺的保护剂以避免催化剂中毒，而且还作为构建恶唑烷-2-酮的反应物。
Carbon dioxide (CO2) has been wildly employed as an environmentally benign C1resource for organic synthesis in the recent years. The capture of CO2with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant for the synthesis of oxazolidin‐2‐onesviathe reaction with aromatic aldehydes and aromatic terminal alkynes. A variety of oxazolidin‐2‐ones with different functional groups were synthesized in 68–91% yields with only a 5 mol% amount of CuI as catalyst. It was found that the synergetic effect of iodide is important for the transformation. Notable, the captured CO2serves not only as a protecting reagent for electron‐rich primary amine to avoid catalyst poisoning, but also as a reactant for the construction of oxazolidin‐2‐ones.