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通过钌纳米催化剂对吲哚进行区域选择性C-H烯基化反应合成3-烯基吲哚。

Synthesis of 3-alkenylindoles through regioselective C-H alkenylation of indoles by a ruthenium nanocatalyst.

作者信息

Paul Abhijit, Chatterjee Debnath, Banerjee Srirupa, Yadav Somnath

机构信息

Department of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, Jharkhand, India.

Department of Chemistry, Bethune College, Bidhan Sarani, Kolkata, 700006, West Bengal, India.

出版信息

Beilstein J Org Chem. 2020 Jan 29;16:140-148. doi: 10.3762/bjoc.16.16. eCollection 2020.

Abstract

3-Alkenylindoles are biologically and medicinally very important compounds, and their syntheses have received considerable attention. Herein, we report the synthesis of 3-alkenylindoles via a regioselective alkenylation of indoles, catalysed by a ruthenium nanocatalyst (RuNC). The reaction tolerates several electron-withdrawing and electron-donating groups on the indole moiety. Additionally, a "robustness screen" has also been employed to demonstrate the tolerance of several functional groups relevant to medicinal chemistry. With respect to the Ru nanocatalyst, it has been demonstrated that it is recoverable and recyclable up to four cycles. Also, the catalyst acts through a heterogeneous mechanism, which has been proven by various techniques, such as ICPMS and three-phase tests. The nature of the Ru nanocatalyst surface has also been thoroughly examined by various techniques, and it has been found that the oxides on the surface are responsible for the high catalytic efficiency of the Ru nanocatalyst.

摘要

3-烯基吲哚是具有重要生物学和药用价值的化合物,其合成受到了广泛关注。在此,我们报道了通过钌纳米催化剂(RuNC)催化吲哚的区域选择性烯基化反应来合成3-烯基吲哚。该反应能耐受吲哚部分上的多个吸电子和供电子基团。此外,还采用了“稳健性筛选”来证明该反应对几种与药物化学相关的官能团的耐受性。关于钌纳米催化剂,已证明其可回收且可循环使用多达四个循环。而且,该催化剂通过非均相机制起作用,这已通过多种技术如电感耦合等离子体质谱法(ICPMS)和三相测试得到证实。还通过各种技术对钌纳米催化剂表面的性质进行了深入研究,发现表面的氧化物是钌纳米催化剂具有高催化效率的原因。

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