Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones
An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels-Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90% yield. Kinetic analysis supporting our proposed mechanism was also performed, underscoring the robustness of the developed synthetic pathway.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:89 |
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| Enthalten in: |
The Journal of organic chemistry - 89(2024), 5 vom: 01. März, Seite 3102-3110 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yoo, Hyung-Seok [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 01.03.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.joc.3c02558 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM368543439 |
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| 100 | 1 | |a Yoo, Hyung-Seok |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones |
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| 500 | |a Date Revised 01.03.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels-Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90% yield. Kinetic analysis supporting our proposed mechanism was also performed, underscoring the robustness of the developed synthetic pathway | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Shin, Jeong-Won |e verfasserin |4 aut | |
| 700 | 1 | |a Jang, Yoon Hu |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Yo-Sep |e verfasserin |4 aut | |
| 700 | 1 | |a Son, Seung Hwan |e verfasserin |4 aut | |
| 700 | 1 | |a Won, Hyuck-Jae |e verfasserin |4 aut | |
| 700 | 1 | |a Kim, Soo Lim |e verfasserin |4 aut | |
| 700 | 1 | |a Sim, Jaehoon |e verfasserin |4 aut | |
| 700 | 1 | |a Kim, Nam-Jung |e verfasserin |4 aut | |
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| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.joc.3c02558 |3 Volltext |
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