Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates
Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates
复制标题
磺酰叠氮与正炔烃或丙酸酯之间铜 (I) 催化的叠氮化物/炔烃环加成 (CuAAC) 的高度控制选择性
DOI：
10.1016/j.tet.2011.06.017
复制
发表时间：
2011-08-26
期刊：
影响因子：
2.1
通讯作者：
Hu, Yuefei
中科院分区：
文献类型：
--
作者：
Liu, Yantao;Wang, Xinyan;Hu, Yuefei
本文以Cu（OAc）（2）·H（2）O/（2）-氨基苯酚为催化剂，研究了CuAAC对磺酰叠氮化合物的高效可控催化体系。利用该催化体系，磺酰叠氮化合物与正炔或炔丙酸酯反应，在几分钟内分别以优异的产率选择性地得到环状产物或链状产物。反应中原位生成的HOAc是一种超质子化试剂，它能有效地将不稳定的中间体5-酮化的1，2，3-三唑质子化，生成环状产物1-磺酰基1，2，3-三唑。对照实验也证明了2-氨基苯酚同时具有配体和还原剂的双重作用，这使得廉价且化学稳定的Cu（OAc）（2）中心点H2O成为我们研究的有效铜源。(C)2011爱思唯尔有限公司保留所有权利。
In this article, a combination of Cu(OAc)(2).H(2)O/(2)-aminophenol was developed as a highly efficient and controlling catalytic system for sulfonyl azids involved CuAAC. By using this catalytic system, sulfonyl azids reacted with normal alkynes or propynoates to selectively give the ring products or the chain products, respectively, in excellent yields within minutes. HOAc in situ produced in the reaction has been proved to be a super protonation reagent, by which the unstable intermediate 5-cuprated 1,2,3-triazole was protonated efficiently to yield ring-product 1-sulfonyl 1,2,3-trizoles. The control experiments also proved that 2-aminophenol played dual roles as both ligand and reductant, which led to the cheap and chemically stable Cu(OAc)(2)center dot H(2)O being an efficient copper source for our purpose. (C) 2011 Elsevier Ltd. All rights reserved.