Journal of Organic Chemistry
Journal of Organic Chemistry
3 years ago

A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation

A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation
Chiaki Yamamoto, Masahiro Miura, Koji Hirano, Kazutaka Takamatsu
A directing-group-controlled, copper-catalyzed divergent approach to indoles and oxazoles from enamides has been developed. The picolinamide-derived enamides undergo the intramolecular aromatic C–H amination in the presence of a Cu(OPiv)2 catalyst and an MnO2 oxidant to form the corresponding indoles in good yields. On the other hand, simpler aryl- or alkyl-substituted enamides are converted to the 2,4,5-trisubstituted oxazole frameworks via vinylic C–H alkoxylation under identical conditions. The copper catalysis can provide uniquely divergent access to indole and oxazole heteroaromatic cores of great importance in medicinal and material chemistry.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01667

DOI: 10.1021/acs.joc.7b01667

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