From ynamides to highly substituted benzo[b]furans: gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates
A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both CO and CC formation steps, thus providing benzofurans with amine function...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
August 6, 2013
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| In: |
Chemistry - a European journal
Year: 2013, Volume: 19, Issue: 37, Pages: 12504-12511 |
| ISSN: | 1521-3765 |
| DOI: | https://doi.org/10.1002/chem.201301595 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/chem.201301595 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201301595 
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| Author Notes: | Maria Camila Blanco Jaimes, Vanessa Weingand, Frank Rominger, and A. Stephen K. Hashmi |
| Summary: | A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both CO and CC formation steps, thus providing benzofurans with amine functionalities at the 2-position and alkyl groups at the 3-position. Cross-over experiments showed that the alkyl-migration step was an intermolecular process. X-ray crystal-structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3-position were obtained as side-products, which were formed through a competing protodeauration process. |
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| Item Description: | Gesehen am 30.04.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | https://doi.org/10.1002/chem.201301595 |