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Updated: May 20, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
From propargylic amides to functionalized oxazoles: domino gold catalysis/oxidation by dioxygen
A Stephen K Hashmi1, Maria Camila Blanco Jaimes, Andreas M Schuster
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany. hashmi@hashmi.de
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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