Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles
3-Chalcogenylindoles serve as crucial building blocks in organic synthesis and pharmaceutical chemistry. Herein, we describe a simple and general synthesis of 3-chalcogenylindoles through the direct C–H chalcogenation of indoles using <i>N</i>-selenophthalimide and <i>N</i>-s...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-04-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/9/1870 |
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| Summary: | 3-Chalcogenylindoles serve as crucial building blocks in organic synthesis and pharmaceutical chemistry. Herein, we describe a simple and general synthesis of 3-chalcogenylindoles through the direct C–H chalcogenation of indoles using <i>N</i>-selenophthalimide and <i>N</i>-sulfenylsuccinimide as chalcogenation reagents in the presence of CuBr<sub>2</sub> as the catalyst. The reactions were carried out in CH<sub>2</sub>Cl<sub>2</sub> at room temperature under an air atmosphere with a low loading of catalyst, and a wide range of 3-selenylindoles and 3-thioindoles were obtained in good yields. Various functionalities, namely, methyl, methoxy, halo, ester, cyano, trifluoromethyl, and formyl groups on indoles, have shown amenability to the developed reaction. A mechanism involving the activation of the chalcogenation agent through CuBr<sub>2</sub> coordination with the amide carbonyl group is proposed. |
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| ISSN: | 1420-3049 |