Brønsted acid-mediated tandem cyclization of triarylphosphines and in situ generated ortho-alkynyl quinone methides : access to heterocyclic quaternary phosphonium salts
Heterocyclic Quaternary Phosphonium Salts (HQPS) have emerged as promising chemicals for organic synthesis and medicinal chemistry. However, the present synthetic methodology of this type of compound is still limited. Here, we report a deconstructive reorganization strategy based on Brønsted acid-mediated tandem 1,4 addition/intramolecular cyclization of triphenylphosphine derivatives and in situ generated o-AQMs for the first time. This protocol provides a novel approach to heterocyclic quaternary phosphonium salts. The method also features a non-metal catalyst, mild reaction conditions, high efficiency and wide substrate scope. Moreover, a series of obtained heterocyclic phosphonium salts can be converted to isotopically labelled 2-benzofuran compounds directly by simple deuteration reactions.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:59 |
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| Enthalten in: |
Chemical communications (Cambridge, England) - 59(2023), 23 vom: 16. März, Seite 3463-3466 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Fan, Ya-Xin [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 20.03.2023 Date Revised 20.03.2023 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d2cc06994f |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM353787426 |
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| 100 | 1 | |a Fan, Ya-Xin |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Brønsted acid-mediated tandem cyclization of triarylphosphines and in situ generated ortho-alkynyl quinone methides |b access to heterocyclic quaternary phosphonium salts |
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| 500 | |a Date Revised 20.03.2023 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Heterocyclic Quaternary Phosphonium Salts (HQPS) have emerged as promising chemicals for organic synthesis and medicinal chemistry. However, the present synthetic methodology of this type of compound is still limited. Here, we report a deconstructive reorganization strategy based on Brønsted acid-mediated tandem 1,4 addition/intramolecular cyclization of triphenylphosphine derivatives and in situ generated o-AQMs for the first time. This protocol provides a novel approach to heterocyclic quaternary phosphonium salts. The method also features a non-metal catalyst, mild reaction conditions, high efficiency and wide substrate scope. Moreover, a series of obtained heterocyclic phosphonium salts can be converted to isotopically labelled 2-benzofuran compounds directly by simple deuteration reactions | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Huang, Hong-Li |e verfasserin |4 aut | |
| 700 | 1 | |a Su, Qing-Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Lv, Yong-Zheng |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Shan |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Yan-Hua |e verfasserin |4 aut | |
| 700 | 1 | |a Mao, Yan-Xin |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Chun-Lin |e verfasserin |4 aut | |
| 700 | 1 | |a Du, Ji-Yuan |e verfasserin |4 aut | |
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