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Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization
Alternative Title钛促进的1,3-共轭双炔与氰基亚胺的交叉偶联反应: 通过imino-aza-Nazarov型环化合成3-氨基吡咯衍生物
You X(尤旭); Jie X(解鑫); Sun RH(孙仁红); Chen HY(陈好益); Li S(李石); Liu YH(刘元红)
2014
Source PublicationOrg. Chem. Front.
Volume1Pages:940-946
AbstractTi(OiPr)4/2 nBuLi-mediated highly efficient cross-coupling reactions of 1,3-butadiynes with α-iminonitriles are described. The method provides convenient access to functionalized 3-aminopyrroles with a wide diversity of substituents in a highly regioselective manner. When optically pure α-iminonitrile is employed in this reaction, a chiral pyrrole derivative is obtained without loss of enantiopurity. Mechanistic study indicates that the 3-aminopyrroles are formed upon treatment of the crude hydrolysis products with silica gel or Lewis acid. A novel imino aza-Nazarov cyclization reaction is proposed to account for the formation of the pyrrole products. Employing the titanium-monoyne complex in this reaction resulted in the homocoupling of α-iminonitriles, leading to the formation of 1,2-diimines.
Subject Area金属有机化学
DOI10.1039/c4qo00159a
URL查看原文
Language英语
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Cited Times:16[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39014
Collection金属有机化学国家重点实验室
Corresponding AuthorLiu YH(刘元红)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
You X,Jie X,Sun RH,et al. Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization[J]. Org. Chem. Front.,2014,1:940-946.
APA 尤旭,解鑫,孙仁红,陈好益,李石,&刘元红.(2014).Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization.Org. Chem. Front.,1,940-946.
MLA 尤旭,et al."Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization".Org. Chem. Front. 1(2014):940-946.
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