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Gold meets selenium: dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insights

Herein, we report the synthesis of seleno-substituted chromenes from selenoalkynes and phenols. In this cascade reaction, the applied gold catalyst not only functions as a π-acid, but also as a Lewis acid, enabling the propargylic substitution in the first step to connect the oxygen carbon bond. Und...

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Main Authors: Lopes, Eric F. (Author) , Dietl, Martin C. (Author) , Ziegler, Benjamin (Author) , Rudolph, Matthias (Author) , Barcellos, Thiago (Author) , Oeser, Thomas (Author) , Lüdtke, Diogo S. (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: November 7, 2024
In: Chemistry - a European journal
Year: 2024, Volume: 30, Issue: 62, Pages: 1-7
ISSN:1521-3765
DOI:10.1002/chem.202402426
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202402426
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202402426
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Author Notes:Eric F. Lopes, Martin C. Dietl, Benjamin Ziegler, Matthias Rudolph, Thiago Barcellos, Thomas Oeser, Diogo S. Lüdtke, and A. Stephen K. Hashmi
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Summary:Herein, we report the synthesis of seleno-substituted chromenes from selenoalkynes and phenols. In this cascade reaction, the applied gold catalyst not only functions as a π-acid, but also as a Lewis acid, enabling the propargylic substitution in the first step to connect the oxygen carbon bond. Under the optimal reaction condition a total of 26 chromenes were accessible by this modular access. During scale up experiments, the hydrolysis of the vinylselenium substructure to the corresponding chromenones was observed. By revisiting the electron-rich starting materials, four chromenones were produced following a one-pot reaction using a single gold catalyst. To better understand the interaction of gold and selenium, a series of nuclear magnetic resonance studies and high-resolution mass spectrometry studies were performed, which led to the proposal of a mechanism for this transformation.
Item Description:Online verfügbar: 19. August 2024
Gesehen am 02.04.2025
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202402426

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