铜(I)催化的常压二氧化碳、炔丙醇和仲胺三组分反应
收稿日期: 2015-12-25
修回日期: 2016-01-30
网络出版日期: 2016-02-18
基金资助
国家自然科学基金(Nos.21472103,21121002)、教育部博士点基金(No.20130031110013)和国家基础科学人才培养基金(No.J1103306)资助项目.
Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO2
Received date: 2015-12-25
Revised date: 2016-01-30
Online published: 2016-02-18
Supported by
Project supported by the National Natural Sciences Foundation of China (Nos. 21472103, 21121002), the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20130031110013) and the National Found for Fostering Talents of Basic Science (No. J1103306).
氨基甲酸酯类化合物是一类重要的有机化合物,在医药、农药以及有机合成中有着广泛应用,也可以作为氨基的保护基团.炔丙醇、仲胺和CO2在铜(I)催化下能够发生三组分"一锅"反应,高收率、高选择性地生成β-羰基氨基甲酸酯.该反应能够在常压CO2的条件下进行,具有反应条件温和、原子经济性高和底物适应范围宽等优点.通过控制氧气含量,可以高选择性地形成β-羰基氨基甲酸酯.多种炔丙醇和仲胺均能高效反应,生成相应的β-羰基氨基甲酸酯.该方法避免了利用高压CO2提高反应效率的问题,是二氧化碳低压温和条件下制备β-羰基氨基甲酸酯类化合物的简便途径.
李雪冬 , 郎咸东 , 宋清文 , 郭亚坤 , 何良年 . 铜(I)催化的常压二氧化碳、炔丙醇和仲胺三组分反应[J]. 有机化学, 2016 , 36(4) : 744 -751 . DOI: 10.6023/cjoc201512037
β-Oxopropylcarbamates constitute an important kind of organic compounds, owing to the extensive applications in agrochemicals, pharmaceuticals, organic synthesis, and protection of amino group. In this article, an efficient and atom-economical Cu(I) catalyzed three-component reaction of propargylic alcohols, secondary amines and CO2 has been developed under atmospheric pressure, affording various β-oxopropylcarbamates in high yields with high selectivity by controlling the concentration of O2. This protocol avoids the use of high pressure of CO2 and provides an extremely simple way to access the synthetically useful β-oxopropylcarbamates.
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