Escape from Palladium : Nickel-Catalyzed Catellani Annulation
While Catellani reactions have become increasingly important for arene functionalizations, they have been solely catalyzed by palladium. Here we report the first nickel-catalyzed Catellani-type annulation of aryl triflates and chlorides to form various benzocyclobutene-fused norbornanes in high efficiency. Mechanistic studies reveal a surprising outer-sphere concerted metalation/deprotonation pathway during the formation of the nickelacycle, as well as the essential roles of the base and the triflate anion. The reaction shows a broad functional group tolerance and enhanced regioselectivity compared to the corresponding palladium catalysis.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:145 |
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| Enthalten in: |
Journal of the American Chemical Society - 145(2023), 20 vom: 24. Mai, Seite 11005-11011 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Huo, Jingfeng [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 24.05.2023 Date Revised 29.03.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/jacs.3c03780 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM356870421 |
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| 245 | 1 | 0 | |a Escape from Palladium |b Nickel-Catalyzed Catellani Annulation |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a While Catellani reactions have become increasingly important for arene functionalizations, they have been solely catalyzed by palladium. Here we report the first nickel-catalyzed Catellani-type annulation of aryl triflates and chlorides to form various benzocyclobutene-fused norbornanes in high efficiency. Mechanistic studies reveal a surprising outer-sphere concerted metalation/deprotonation pathway during the formation of the nickelacycle, as well as the essential roles of the base and the triflate anion. The reaction shows a broad functional group tolerance and enhanced regioselectivity compared to the corresponding palladium catalysis | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Fu, Yue |e verfasserin |4 aut | |
| 700 | 1 | |a Tang, Melody J |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Peng |e verfasserin |4 aut | |
| 700 | 1 | |a Dong, Guangbin |e verfasserin |4 aut | |
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