Metal-Free, Redox-Neutral, Site-Selective Access to Heteroarylamine via Direct Radical-Radical Cross-Coupling Powered by Visible Light Photocatalysis
Transition-metal-catalyzed C-N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical-radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C-N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C-N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:142 |
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| Enthalten in: |
Journal of the American Chemical Society - 142(2020), 39 vom: 30. Sept., Seite 16805-16813 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhou, Chao [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 22.01.2021 Date Revised 22.01.2021 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/jacs.0c07600 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM314697691 |
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| 245 | 1 | 0 | |a Metal-Free, Redox-Neutral, Site-Selective Access to Heteroarylamine via Direct Radical-Radical Cross-Coupling Powered by Visible Light Photocatalysis |
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| 500 | |a Date Completed 22.01.2021 | ||
| 500 | |a Date Revised 22.01.2021 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Transition-metal-catalyzed C-N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical-radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C-N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C-N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Lei, Tao |e verfasserin |4 aut | |
| 700 | 1 | |a Wei, Xiang-Zhu |e verfasserin |4 aut | |
| 700 | 1 | |a Ye, Chen |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Zan |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Bin |e verfasserin |4 aut | |
| 700 | 1 | |a Tung, Chen-Ho |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Li-Zhu |e verfasserin |4 aut | |
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