From propargylic amides to functionalized oxazoles: domino gold catalysis/oxidation by dioxygen |
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Authors: | A Stephen K Hashmi Maria Camila Blanco Jaimes Andreas M Schuster Frank Rominger |
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Affiliation: | Organisch-Chemisches Institut, Ruprecht-Karls-Universit?t Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany. |
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Abstract: | 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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