On the gold-Catalyzed generation of vinyl cations from 1,5-diynes

Conjugated 1,5-diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl-substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional a...

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Bibliographic Details
Main Authors: Wurm, Thomas (Author) , Bucher, Janina (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: March 13, 2017
In: Angewandte Chemie. International edition
Year: 2017, Volume: 56, Issue: 12, Pages: 3364-3368
ISSN:1521-3773
DOI:10.1002/anie.201700057
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201700057
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201700057
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Author Notes:Thomas Wurm, Janina Bucher, Sarah B. Duckworth, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Description
Summary:Conjugated 1,5-diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl-substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional approach provided selective access to the angular annulated product in high yield, which was explained by calculations.
Item Description:First published: 14 February 2017
Gesehen am 18.10.2018
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201700057