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Metal-free oxidative cyclization of alkynyl aryl ethers to benzofuranones

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Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Brønsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained...

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Bibliographic Details
Main Authors: Graf, Katharina (Author) , Rühl, Carmen L. (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: October 7, 2013
In: Angewandte Chemie. International edition
Year: 2013, Volume: 52, Issue: 48, Pages: 12727-12731
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.201304813
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/anie.201304813
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201304813
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Author Notes:Katharina Graf, Carmen L. Rühl, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary:Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Brønsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α-oxy carbene precursors even in the absence of a metal catalyst.
Item Description:Gesehen am 24.02.2020
Physical Description:Online Resource
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.201304813

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