Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 17, Pages 9112-9118Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01667
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Funding
- JSPS KAKENHI [JP 17J00349, JP 15K13696, JP 15H05485, JP 17H01202, JP 17H06092]
- Grants-in-Aid for Scientific Research [17H01202, 17H06092, 17J00349, 15H05485] Funding Source: KAKEN
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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.
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