Au-Ag bimetallic catalysis: 3-alkynyl benzofurans from phenols via tandem C-H alkynylation/oxy-alkynylation

The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C−H alkynylation of phenols and oxy-alkynylation of the newly introduced triple bond by using a uni...

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Hauptverfasser: Hu, Long (VerfasserIn) , Dietl, Martin C. (VerfasserIn) , Han, Chunyu (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 22 February 2021
In: Angewandte Chemie. International edition
Year: 2021, Jahrgang: 60, Heft: 19, Pages: 10637-10642
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.202016595
Online-Zugang:Resolving-System, kostenfrei, Volltext: https://doi.org/https://doi.org/10.1002/anie.202016595
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202016595
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Verfasserangaben:Long Hu, Martin C. Dietl, Chunyu Han, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Zusammenfassung:The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C−H alkynylation of phenols and oxy-alkynylation of the newly introduced triple bond by using a unique redox property and the carbophilic π acidity of gold. Mechanistic studies support the participation of a bimetallic gold-silver species. The one-pot protocol offers a direct, simple, and regio-specific approach to 3-alkynyl benzofurans from readily available phenols. A broad range of substrates, including heterocycles, is transferred with excellent functional group tolerance. Thus, this methodology can be used for the late-stage incorporation of benzofurans.
Beschreibung:Gesehen am 21.04.2021
Beschreibung:Online Resource
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.202016595