期刊
TETRAHEDRON
卷 67, 期 34, 页码 6294-6299出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.017
关键词
Copper(I) catalyst; Azide/alkyne cycloaddition; Sulfonyl azids; Copper(II) acetate; 2-Aminophenol
资金
- National Natural Science Foundation of China [21072112]
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.
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