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Synthesis of Indoles via Electron-Catalyzed Intramolecular C–N Bond Formation
A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C–N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number of substrates, indoles were afforded in yields...
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| Published in: | Organic letters 2018-12, Vol.20 (23), p.7358-7362 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a345t-fb881f0aabc676cee87cc866f911b10551c8fbd7fa4dc9629aab5914b6b113303 |
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| cites | cdi_FETCH-LOGICAL-a345t-fb881f0aabc676cee87cc866f911b10551c8fbd7fa4dc9629aab5914b6b113303 |
| container_end_page | 7362 |
| container_issue | 23 |
| container_start_page | 7358 |
| container_title | Organic letters |
| container_volume | 20 |
| creator | Bugaenko, Dmitry I Dubrovina, Anastasia A Yurovskaya, Marina A Karchava, Alexander V |
| description | A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C–N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number of substrates, indoles were afforded in yields higher or comparable to those obtained under transition-metal-catalyzed conditions. While demonstrating high functional group tolerance, new conditions are particularly attractive for manufacturing halogenated indoles that cannot be made in a pure form using other metal-based catalytic methods. |
| doi_str_mv | 10.1021/acs.orglett.8b02784 |
| format | article |
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| ispartof | Organic letters, 2018-12, Vol.20 (23), p.7358-7362 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2133827685 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| title | Synthesis of Indoles via Electron-Catalyzed Intramolecular C–N Bond Formation |
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