Cascade reactions of aryl-substituted terminal alkynes involving in situ-generated α-imino gold carbenes
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...
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| Hauptverfasser: | , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
January 25, 2024
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| In: |
Angewandte Chemie. International edition
Year: 2024, Jahrgang: 63, Heft: 5, Pages: 1-6 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202313738 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202313738 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202313738 
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| Verfasserangaben: | Qiaoying Sun, Christopher Hüßler, Justin Kahle, Alexandra V. Mackenroth, Matthias Rudolph, Petra Krämer, Thomas Oeser, and A. Stephen K. Hashmi |
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| 245 | 1 | 0 | |a Cascade reactions of aryl-substituted terminal alkynes involving in situ-generated α-imino gold carbenes |c Qiaoying Sun, Christopher Hüßler, Justin Kahle, Alexandra V. Mackenroth, Matthias Rudolph, Petra Krämer, Thomas Oeser, and A. Stephen K. Hashmi |
| 246 | 3 | 3 | |a Cascade reactions of aryl-substituted terminal alkynes involving in situ-generated alpha-imino gold carbenes |
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| 520 | |a 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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| 650 | 4 | |a Terminal Alkynes | |
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