Gold-Catalyzed β-Regioselective Formal [3+2] Cycloaddition of Ynamides with Pyrido[1,2-b]indazoles: Reaction Development and Mechanistic Insights

被引：38
|
作者：
Yu, Yinghua [1 ]
Chen, Gui [1 ]
Zhu, Lei [1 ]
Liao, Yun [1 ,2 ]
Wu, Yufeng [1 ,2 ]
Huang, Xueliang [1 ]
机构：
[1] Chinese Acad Sci, Key Lab Coal Ethylene Glycol & Its Related Techno, Fujian Inst Res Struct Matter, Yangqiao West Rd 155, Fuzhou 350002, Fujian, Peoples R China
[2] Fuzhou Univ, Coll Chem, Fuzhou 350108, Fujian, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 18期
关键词：
NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; INTERMOLECULAR NITRENE TRANSFER; PROTON-ABSTRACTION MECHANISM; INTRAMOLECULAR ARYLATION; SKELETAL REARRANGEMENT; SELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; PROPARGYL ALCOHOLS; TERMINAL ALKYNES;
D O I：
10.1021/acs.joc.6b01948
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Here, we report an unprecedented gold(I)-induced beta-site regioselective formal [3 + 2] cycloaddition of ynamides with pyrido[1,2-b]indazoles, giving 3-amido-7-(pyrid-2'-yl)indoles in good to excellent yields. A complex of gold(I) catalyst with ynamide was isolated and characterized by X-ray diffraction analysis for the first time. Mechanistic investigations suggest the reaction pathway involves a gold-stabilized carbocation intermediate, which in turn participated in sequential C-H bond functionalization of the ortho-position of the phenyl ring.
引用
收藏
页码：8142 / 8154
页数：13
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