铜介导的胺和铵促进的吲哚 C3-氰化反应。

Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium.

机构信息

College of Chemistry & Engineering, Wenzhou University, Wenzhou, 325000, P. R. China.

出版信息

Chem Commun (Camb). 2014 Mar 4;50(18):2315-7. doi: 10.1039/c3cc49339c. Epub 2014 Jan 21.

Abstract

A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N',N'-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O followed by hydrolyzation to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O2 as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles.

摘要

一种铜促进的 N,N,N',N'-四甲基乙二胺（TMEDA）和铵盐促进的游离 N-H 和 N-保护吲哚的 C3-氰化反应已经实现。亚胺离子作为这种转化的中间体，依次受到吲哚和 H2O 的亲电攻击，然后水解形成醛。然后，醛与铵反应生成腈。该反应采用 O2 作为清洁氧化剂，具有良好的效率和官能团耐受性。因此，它代表了一种简单安全的方法，可得到 3-氰基吲哚。