From propargylic amides to functionalized oxazoles: Domino gold catalysis/oxidation by dioxygen
A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroper...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
July 17, 2012
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| In: |
The journal of organic chemistry
Year: 2012, Volume: 77, Issue: 15, Pages: 6394-6408 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo301288w |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1021/jo301288w Verlag, Volltext: http://pubs.acs.org/doi/10.1021/jo301288w 
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| Author Notes: | A. Stephen K. Hashmi, Maria Camila Blanco Jaimes, Andreas M. Schuster, and Frank Rominger |
| Summary: | A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride. |
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| Item Description: | Gesehen am 06.09.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo301288w |