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学科主题: 金属有机化学
题名: Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization
其他题名: 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
作者: 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)
通讯作者: 刘元红
刊名: Org. Chem. Front.
发表日期: 2014
DOI: 10.1039/c4qo00159a
卷: 1, 页:940-946
英文摘要: Ti(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.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39014
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所

Recommended Citation:
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.
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