Microwave-Assisted or Cu-NHC-Catalyzed Cycloaddition of Azido-Disubstituted Alkynes: Bifurcation of Reaction Pathways

被引：24
作者：
Xia, Yuyu [1 ]
Chen, Ling-yan [1 ]
Lv, Shang [1 ]
Sun, Zhihua [1 ]
Wang, Bing [2 ,3 ]
机构：
[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, Shanghai 201620, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[3] Fudan Univ, Inst Biomed Sci, Shanghai 200032, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 20期
基金：
中国国家自然科学基金;
关键词：
N-HETEROCYCLIC CARBENES; CLICK CHEMISTRY; ORGANIC AZIDES; TERMINAL ALKYNES; COPPER(I)-CATALYZED CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; HUISGEN CYCLOADDITION; ASYMMETRIC-SYNTHESIS; 1,2,3-TRIAZOLES; ESTERS;
D O I：
10.1021/jo5011262
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Microwave irradiation promoted the intramolecular cycloaddition of 2-azidoacetamides derived from a-chiral propargylic amines, affording 1,4,5-trisubstituted triazoles 4 bearing a chiral aminomethyl side chain at C5. In contrast, for the same substrates 3a-k, Cu(I)-NHC complexes catalyzed the intermolecular cycloaddition in an unexpected desilylative fashion, leading to 1,4-disubstituted triazoles 5. This demonstrates that 1-silyl alkynes can be employed as substrates for CuAAC with a suitable coupling partner.
引用
收藏
页码：9818 / 9825
页数：8
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