Dehydrogenative Meyer-Schuster-like rearrangement: a gold-catalyzed reaction generating an alkyne
Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz’s catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2014
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| In: |
Angewandte Chemie. International edition
Year: 2013, Volume: 53, Issue: 4, Pages: 1144-1147 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201307647 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/anie.201307647 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201307647 
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| Author Notes: | Yang Yu, Weibo Yang, Daniel Pflästerer, and A. Stephen K. Hashmi |
| Summary: | Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz’s catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer-Schuster rearrangement. |
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| Item Description: | Published online: December 11, 2013 Gesehen am 14.10.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201307647 |