Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 6, Pages 3242-3249Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00307
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Funding
- MEXT
- JSPS of Japan
- Grants-in-Aid for Scientific Research [25620084, 25288048] Funding Source: KAKEN
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A Cu(OAc)(2)-mediated intramolecular aromatic C-H amination proceeds with the aid of a picolinamide-type bidentate coordination group to deliver the corresponding indolines in good yields. The reaction occurs smoothly even under noble-metal-free conditions, and in some cases the use of an MnO2 terminal oxidant renders the process catalytic in Cu. The mild oxidation aptitude of Cu(OAc)(2) and/or MnO2 accommodates the formation of electron-rich thiophene- and indole-fused indoline analogues. The Cu-based system can provide an effective approach to various indolines of potent interest in pharmaceutical and medicinal chemistry.
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