Lewis-Acid-Catalyzed (3+2) Annulation of 2-Indolylmethanols with Propargylic Alcohols to Access Cyclopenta[b]indoles
Herein, a Sc(OTf)3-catalyzed (3+2) annulation of 2-indolylmethanols with propargylic alcohols is reported. The reaction proceeds via a Friedel-Crafts-type allenylation/5-exo-annulation cascade. In the reaction, 2-indolylmethanol is used as a three-carbon synthon, and propargyl alcohol is used as a two-carbon synthon. This method provides a direct and high-yield pathway for synthetically useful cyclopenta[b]indoles. In general, the method features easily accessible substrates with broad scope and generality, the formation of multiple bonds with high efficiency, and easy scale-up.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:29 |
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| Enthalten in: |
Molecules (Basel, Switzerland) - 29(2024), 6 vom: 12. März |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Wu, Teng-Fei [VerfasserIn] |
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| Links: |
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| Themen: |
(3+2) annulation |
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| Anmerkungen: |
Date Revised 30.03.2024 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.3390/molecules29061251 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM370324315 |
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| 245 | 1 | 0 | |a Lewis-Acid-Catalyzed (3+2) Annulation of 2-Indolylmethanols with Propargylic Alcohols to Access Cyclopenta[b]indoles |
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| 500 | |a Date Revised 30.03.2024 | ||
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| 520 | |a Herein, a Sc(OTf)3-catalyzed (3+2) annulation of 2-indolylmethanols with propargylic alcohols is reported. The reaction proceeds via a Friedel-Crafts-type allenylation/5-exo-annulation cascade. In the reaction, 2-indolylmethanol is used as a three-carbon synthon, and propargyl alcohol is used as a two-carbon synthon. This method provides a direct and high-yield pathway for synthetically useful cyclopenta[b]indoles. In general, the method features easily accessible substrates with broad scope and generality, the formation of multiple bonds with high efficiency, and easy scale-up | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a (3+2) annulation | |
| 650 | 4 | |a 2-indolylmethanols | |
| 650 | 4 | |a cyclopenta[b]indoles | |
| 650 | 4 | |a propargylic alcohols | |
| 700 | 1 | |a Fu, Zhao-Jie |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yi-Rui |e verfasserin |4 aut | |
| 700 | 1 | |a Qiu, Zong-Wang |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Bao Qiong |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Shao-Shuai |e verfasserin |4 aut | |
| 700 | 1 | |a Pan, Han-Peng |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Ai-Jun |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Xiang-Zhi |e verfasserin |4 aut | |
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