کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5219972 | 1383373 | 2011 | 6 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: 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](/preview/png/5219972.png)
In this article, a combination of Cu(OAc)2·H2O/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·H2O being an efficient copper source for our purpose.
Journal: Tetrahedron - Volume 67, Issue 34, 26 August 2011, Pages 6294-6299