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Synthesis of 3-alkenylindoles through regioselective C-H alkenylation of indoles by a ruthenium nanocatalyst.
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-01-29 , DOI: 10.3762/bjoc.16.16
Abhijit Paul 1 , Debnath Chatterjee 1 , Srirupa Banerjee 2 , Somnath Yadav 1
Affiliation  

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.

中文翻译:

通过钌纳米催化剂通过吲哚的区域选择性CH烯基化合成3-烯基吲哚。

3-烯基吲哚是生物学上和医学上非常重要的化合物,其合成已受到相当大的关注。在本文中,我们报道了通过钌纳米催化剂(RuNC)催化的吲哚的区域选择性烯基化合成3-烯基吲哚。该反应耐受吲哚部分上的几个吸电子和给电子基团。另外,还使用“健壮性筛选”来证明与药物化学有关的几个官能团的耐受性。关于Ru纳米催化剂,已经证明它是可回收的并且可循环使用多达四个循环。而且,催化剂通过非均质机理起作用,该机理已通过各种技术(如ICPMS和三相测试)证明。
更新日期:2020-01-29
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