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Synthesis 2020; 52(01): 75-84
DOI: 10.1055/s-0039-1690240
DOI: 10.1055/s-0039-1690240
paper
Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
We are grateful for financial support from the Fundamental Research Funds for the Central Universities (2572018AB11), National Innovation Experiment Program for University Students (201810225098), and Natural Science Foundation of Heilongjiang Province (B2017002).Further Information
Publication History
Received: 26 July 2019
Accepted after revision: 15 October 2019
Publication Date:
05 November 2019 (online)
§ These authors contributed equally to this work
Abstract
Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates in the presence of CuCl2/phenanthroline, KMnO4, and KHCO3 at 120 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C–H bond in mixed solvents (benzene/DMSO 1:1) at 130 °C affording multi-substituted indoles in good to high yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690240.
- Supporting Information
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For copper-catalyzed indole synthesis, see: