湖南大学周永波团队报道了铜介导的选择性多重惰性化学键裂解通过串联碳和氮原子转移进行吲哚氰化反应。相关研究成果于2024年5月22日发表于国际一流学术期刊《中国化学》。

惰性化学键的活化是化学中一个令人兴奋的研究领域，因为它能够直接利用现成的起始材料，并促进原子和分步经济合成。毫无疑问，在合成化学中，选择性激活和转化多个惰性化学键是一项更有趣、要求更高的任务。然而，由于其固有的复杂性和极端的挑战，这项工作很少能够完成。

该文中，研究人员报道了铜介导的三种容易获得的原料的多个惰性化学键的完全切割和选择性转化，即吲哚中的一个sp²C-H键，TMEDA中甲基碳原子中的三个sp³C-H键和一个C-N键，以及CH₃CN中的C≡N键。该反应通过碳和氮原子的串联转移进行，并实现吲哚的直接有效的氰化，为合成3-氰基吲哚提供了一种简单直接的替代方案。

附：英文原文

Title: Copper-Mediated Selective Multiple Inert Chemical Bonds Cleavage for Cyanation of Indoles via Tandem Carbon and Nitrogen Atom Transfer

Author: Shimin Xie, Fangfang Cai, Lixin Liu, Lebin Su, Jianyu Dong, Yongbo Zhou

Issue&Volume: 2024-05-22

Abstract: The activation of inert chemical bonds is an exciting area of research in chemistry because it enables the direct utilization of readily available starting materials and promotes atom- and step-economic synthesis. Undoubtedly, selectively activating and transforming multiple inert chemical bonds is an even more intriguing and demanding task in synthetic chemistry. However, due to its inherent complexity and extreme challenges, this endeavour is rarely accomplished. We report a copper-mediated complete cleavage and selective transformation of multiple inert chemical bonds of three easily available feedstocks, i.e., a sp2C—H bond in indoles, three sp3C—H bonds and one C—N bond in a methyl carbon atom in TMEDA, and the C≡N triple bond in CH3CN. This reaction proceeds via tandem carbon and nitrogen atom transfer, and allows for the direct and efficient cyanation of indoles, presenting a simple and direct alternative for synthesizing 3-cyanoindoles.

DOI: 10.1002/cjoc.202400062

Source: https://onlinelibrary.wiley.com/doi/full/10.1002/cjoc.202400062