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Gold-catalyzed C(sp2)-C(sp) coupling by alkynylation through oxidative addition of bromoalkynes

A gold(I)-catalyzed cascade cyclization-alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad fun...

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Main Authors: Yang, Yangyang (Author) , Schießl, Jasmin (Author) , Göker, Verena (Author) , Gross, Jürgen H. (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 15 May 2019
In: Chemistry - a European journal
Year: 2019, Volume: 25, Issue: 41, Pages: 9624-9628
ISSN:1521-3765
DOI:10.1002/chem.201902213
Online Access:Resolving-System, Volltext: https://doi.org/10.1002/chem.201902213
Verlag: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201902213
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Author Notes:Yangyang Yang, Jasmin Schießl, Sirine Zallouz, Verena Göker, Jürgen Gross, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary:A gold(I)-catalyzed cascade cyclization-alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant.
Item Description:Im Titel erscheint die Ziffer 2 hochgestellt
Version of record online: June 26, 2019
Gesehen am 07.11.2019
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201902213

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