Nickel-catalyzed three-component carboamination/cyclization of alkynes to access 2,3-disubstituted quinolines
Presented herein is a nickel-catalyzed chemo- and regioselective three-component tandem carboamination and cyclization of terminal alkynes with organoboronic acids and anthranils for facile and modular access to 2,3-substituted quinolines. In this process, anthranil has dual roles: serving as an ele...
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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
January 23, 2025
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| In: |
Organic letters
Year: 2025, Volume: 27, Issue: 5, Pages: 1204-1209 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.4c04753 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1021/acs.orglett.4c04753 Verlag, kostenfrei, Volltext: https://pubs.acs.org/doi/10.1021/acs.orglett.4c04753 
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| Author Notes: | Yang Gao, Jiale Xing, Yanping Huo, Qian Chen, Xianwei Li, A. Stephen K. Hashmi, and Zhongyi Zeng |
| Summary: | Presented herein is a nickel-catalyzed chemo- and regioselective three-component tandem carboamination and cyclization of terminal alkynes with organoboronic acids and anthranils for facile and modular access to 2,3-substituted quinolines. In this process, anthranil has dual roles: serving as an electrophilic aminating reagent and a redox buffer to suppress the generation of an off-cycle Ni(0) complex. Moreover, the anionic acetylacetonate (acac) ligand was found to be vital to ensure a productive Ni(I)-Ni(III)-Ni(I) catalytic cycle. |
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| Item Description: | Gesehen am 28.08.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.4c04753 |