Jagtap Prafull A, Lokolkar Manjunath S, Bhanage Bhalchandra M
Department of Chemistry, Institute of Chemical Technology, Mumbai 400019, India.
J Org Chem. 2023 Aug 4;88(15):10960-10973. doi: 10.1021/acs.joc.3c00954. Epub 2023 Jul 18.
A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds has been developed. The present protocol involves copper-mediated tandem hydroamination followed by C-H annulation of unprotected anilines with a wide range of internal alkynes. In the presence of Cu(OAc)·HO and trifluoroacetic acid (TFA), the reaction proceeds well to afford a variety of substituted indole derivatives in moderate to good yields. This process was found to be compatible with both primary and secondary anilines coupled with aromatic/aliphatic alkynes. High-purity copper nanoparticles can be recovered after the reaction, revealing the cost-effectiveness and environmentally benign feature of the current protocol.
已开发出一种简单、经济高效且直接的合成2,3-二取代吲哚骨架的方法。本方法涉及铜介导的串联氢胺化反应，随后是未保护的苯胺与多种内炔烃的C-H环化反应。在醋酸铜·水合物和三氟乙酸（TFA）存在下，反应顺利进行，以中等至良好的产率得到各种取代的吲哚衍生物。发现该过程与伯胺和仲胺与芳族/脂肪族炔烃的偶联均兼容。反应后可回收高纯度的铜纳米颗粒，这揭示了本方法的成本效益和环境友好特性。
