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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MDPI AG
2025-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/9/1870 |
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| author | Liuyan Pan Shengwei Chen Dongfang Wu Jian Shao Xiaofeng Bao Gong-Qing Liu |
| author_facet | Liuyan Pan Shengwei Chen Dongfang Wu Jian Shao Xiaofeng Bao Gong-Qing Liu |
| author_sort | Liuyan Pan |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-6184d5c2536146db93155c7d149fdc60 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-6184d5c2536146db93155c7d149fdc602025-08-20T02:58:47ZengMDPI AGMolecules1420-30492025-04-01309187010.3390/molecules30091870Copper(II)-Catalyzed Direct C3 Chalcogenylation of IndolesLiuyan Pan0Shengwei Chen1Dongfang Wu2Jian Shao3Xiaofeng Bao4Gong-Qing Liu5Nantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, ChinaNantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, ChinaNantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, ChinaNantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, ChinaNantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, ChinaNantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, China3-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.https://www.mdpi.com/1420-3049/30/9/1870chalcogenationindolesselenylindolessulfenylindolesCuBr<sub>2</sub> |
| spellingShingle | Liuyan Pan Shengwei Chen Dongfang Wu Jian Shao Xiaofeng Bao Gong-Qing Liu Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles Molecules chalcogenation indoles selenylindoles sulfenylindoles CuBr<sub>2</sub> |
| title | Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles |
| title_full | Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles |
| title_fullStr | Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles |
| title_full_unstemmed | Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles |
| title_short | Copper(II)-Catalyzed Direct C3 Chalcogenylation of Indoles |
| title_sort | copper ii catalyzed direct c3 chalcogenylation of indoles |
| topic | chalcogenation indoles selenylindoles sulfenylindoles CuBr<sub>2</sub> |
| url | https://www.mdpi.com/1420-3049/30/9/1870 |
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