Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents
A green one-pot 2,3,6-trifunctionalization of <i>N</i>-alkyl/aryl indoles was achieved by adding three equivalents of <i>N</i>-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using <i>N</i>-B...
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/8/3380 |
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| author | Xiao Yun Chen Yaonan Tang Xinran Xiang Yisong Tang Mingyang Huang Shaojun Zheng Cuifeng Yang |
| author_facet | Xiao Yun Chen Yaonan Tang Xinran Xiang Yisong Tang Mingyang Huang Shaojun Zheng Cuifeng Yang |
| author_sort | Xiao Yun Chen |
| collection | DOAJ |
| description | A green one-pot 2,3,6-trifunctionalization of <i>N</i>-alkyl/aryl indoles was achieved by adding three equivalents of <i>N</i>-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using <i>N</i>-Br sulfoximines as both brominating and sulfoximinating reagents. Based on the results of controlled experiments, we propose that a radical substitution involving 3,6-dibromination and 2-sulfoximination occurs in the reaction process. This is first time that 2,3,6-trifunctionalization of indole in one pot has been achieved. |
| first_indexed | 2024-03-11T04:40:55Z |
| format | Article |
| id | doaj.art-027494b6682c423086c53f33b1a4dadd |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:40:55Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-027494b6682c423086c53f33b1a4dadd2023-11-17T20:38:12ZengMDPI AGMolecules1420-30492023-04-01288338010.3390/molecules28083380Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating ReagentsXiao Yun Chen0Yaonan Tang1Xinran Xiang2Yisong Tang3Mingyang Huang4Shaojun Zheng5Cuifeng Yang6School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, ChinaSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, ChinaSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, ChinaSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, ChinaSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, ChinaSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, ChinaModern Chemistry Research Institute of Xi’an, Xi’an 710065, ChinaA green one-pot 2,3,6-trifunctionalization of <i>N</i>-alkyl/aryl indoles was achieved by adding three equivalents of <i>N</i>-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using <i>N</i>-Br sulfoximines as both brominating and sulfoximinating reagents. Based on the results of controlled experiments, we propose that a radical substitution involving 3,6-dibromination and 2-sulfoximination occurs in the reaction process. This is first time that 2,3,6-trifunctionalization of indole in one pot has been achieved.https://www.mdpi.com/1420-3049/28/8/33802,3,6-trifunctionalization of indoles<i>N</i>-Br sulfoximinesbrominating reagentsulfoximinating reagent |
| spellingShingle | Xiao Yun Chen Yaonan Tang Xinran Xiang Yisong Tang Mingyang Huang Shaojun Zheng Cuifeng Yang Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents Molecules 2,3,6-trifunctionalization of indoles <i>N</i>-Br sulfoximines brominating reagent sulfoximinating reagent |
| title | Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents |
| title_full | Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents |
| title_fullStr | Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents |
| title_full_unstemmed | Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents |
| title_short | Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using <i>N</i>-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents |
| title_sort | green one pot syntheses of 2 sulfoximidoyl 3 6 dibromo indoles using i n i br sulfoximines as both brominating and sulfoximinating reagents |
| topic | 2,3,6-trifunctionalization of indoles <i>N</i>-Br sulfoximines brominating reagent sulfoximinating reagent |
| url | https://www.mdpi.com/1420-3049/28/8/3380 |
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