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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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Main Authors: Sun, Qiaoying (Author) , Hüßler, Christopher (Author) , Kahle, Justin (Author) , Mackenroth, Alexandra (Author) , Rudolph, Matthias (Author) , Krämer, Petra (Author) , Oeser, Thomas (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: January 25, 2024
In: Angewandte Chemie. International edition
Year: 2024, Volume: 63, Issue: 5, Pages: 1-6
ISSN:1521-3773
DOI:10.1002/anie.202313738
Online Access: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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Author Notes:Qiaoying Sun, Christopher Hüßler, Justin Kahle, Alexandra V. Mackenroth, Matthias Rudolph, Petra Krämer, Thomas Oeser, and A. Stephen K. Hashmi
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Summary: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 %.
Item Description:Zuerst veröffentlicht: 26. Oktober 2023
Gesehen am 22.02.2024
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.202313738

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