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Gold-catalyzed cyclisation by 1,4-dioxidation

Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphen...

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Bibliographic Details
Main Authors: Claus, Vanessa (Author) , Molinari, Lise (Author) , Büllmann, Simon (Author) , Thusek, Jean (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 04 March 2019
In: Chemistry - a European journal
Year: 2019, Volume: 25, Issue: 40, Pages: 9385-9389
ISSN:1521-3765
DOI:10.1002/chem.201900996
Online Access:Resolving-System, Volltext: https://doi.org/10.1002/chem.201900996
Verlag: https://www.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201900996
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Author Notes:Vanessa Claus, Lise Molinari, Simon Büllmann, Jean Thusek, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary:Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides.
Item Description:Version of record online: April 17, 2019
Gesehen am 07.11.2019
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201900996

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