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Copper‐Catalyzed Hydroamination of N‐Allenylazoles: Access to Amino‐Substituted N‐Vinylazoles
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-10-16 , DOI: 10.1002/adsc.201700965
Luca Alessandro Perego 1, 2 , Rémi Blieck 3 , Julie Michel 3 , Ilaria Ciofini 1 , Laurence Grimaud 2 , Marc Taillefer 3 , Florian Monnier 3, 4
Affiliation  

Building on mechanistic studies, the innate capability of azoles to act as a directing group has been exploited to design an efficient and simple procedure for the hydroamination of N‐allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio‐ and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N‐allenyl‐(1,2)‐azoles compared to their 1,3‐analogues as a result of the reaction‐enhancing coordination of the pyridine‐like nitrogen to the copper center.

中文翻译:

N-烯丙基唑的铜催化加氢胺化:获得氨基取代的N-乙烯基唑的途径

在机理研究的基础上,已利用吡咯类化合物作为引导基团的先天能力来设计一种有效而简单的程序,用于将N-烯丙基唑类化合物与仲胺进行加氢胺化。在铜(I)催化下,反应在温和条件下进行,得到相应的原始线性E烯丙基胺,具有总的区域和立体选择性。密度泛函理论(DFT)计算提供了一种机械解释,表明N-烯丙基-(1,2)-吡咯的反应活性明显高于其1,3-类似物,这是由于类似吡啶的反应增强了配位作用氮到达铜中心。
更新日期:2017-10-16
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