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| Verfasst von: | Sun, Qiaoying [VerfasserIn]  |
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| | Hüßler, Christopher [VerfasserIn] |
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| | Kahle, Justin [VerfasserIn] |
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| | Mackenroth, Alexandra [VerfasserIn] |
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| | Rudolph, Matthias [VerfasserIn] |
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| | Krämer, Petra [VerfasserIn] |
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| | Oeser, Thomas [VerfasserIn] |
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| | Hashmi, A. Stephen K. [VerfasserIn] |
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| Titel: | Cascade reactions of aryl-substituted terminal alkynes involving in situ-generated α-imino gold carbenes |
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| Verf.angabe: | Qiaoying Sun, Christopher Hüßler, Justin Kahle, Alexandra V. Mackenroth, Matthias Rudolph, Petra Krämer, Thomas Oeser, and A. Stephen K. Hashmi |
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| E-Jahr: | 2024 |
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| Jahr: | January 25, 2024 |
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| Umfang: | 6 S. |
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| Illustrationen: | Illustrationen |
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| Fussnoten: | Zuerst veröffentlicht: 26. Oktober 2023 ; Gesehen am 22.02.2024 |
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| Titel Quelle: | Enthalten in: Angewandte Chemie. International edition |
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| Ort Quelle: | Weinheim : Wiley-VCH, 1998 |
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| Jahr Quelle: | 2024 |
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| Band/Heft Quelle: | 63(2024), 5 vom: Jan., Artikel-ID e202313738, Seite 1-6 |
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| ISSN Quelle: | 1521-3773 |
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| Abstract: | An efficient, highly selective and divergent synthetic method to construct 2-substituted indoles and aryl-annulated carbazoles via the intermolecular generation of α-imino gold carbenes from terminal alkynes or diynes in combination with sulfilimines is disclosed. Importantly, the tandem reaction is proposed to proceed through an intermolecular gold carbene generation/C−H annulation followed by the activation of a second alkyne leading to 6-endo-dig cyclization, which is significantly different from previous dual activation or 1,6-carbene shift approaches for diyne systems. In the case of ortho-alkynylaniline as starting material, an unexpected regioselective formation of the indole moiety via the intermolecular path, instead of intramolecular hydroamination was discovered. This reactivity paved the way for a one-pot synthesis of the 11H-indolo [3,2-c] quinoline scaffold by exploiting the formed amino indole for a subsequent Pictet-Spengler reaction with aldehydes. The photophysical properties of the carbazoles indicated good violet-blue emission with quantum yields up to 40 %. |
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| DOI: | doi:10.1002/anie.202313738 |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
kostenfrei: Volltext: https://doi.org/10.1002/anie.202313738 |
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| | kostenfrei: Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202313738 |
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| | DOI: https://doi.org/10.1002/anie.202313738 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| Sach-SW: | Cascade Reactions |
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| | Diynes |
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| | Sulfilimines |
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| | Terminal Alkynes |
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| K10plus-PPN: | 1881442705 |
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| Verknüpfungen: | → Zeitschrift |
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Cascade reactions of aryl-substituted terminal alkynes involving in situ-generated α-imino gold carbenes / Sun, Qiaoying [VerfasserIn]; January 25, 2024 (Online-Ressource)
