Nickel-Catalyzed C(sp2)–H/C(sp3)–H Oxidative Coupling of Indoles with Toluene Derivatives
| Autor: | Vineeta Soni, Shrikant M. Khake, Benudhar Punji |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Indole test
010405 organic chemistry Chemistry chemistry.chemical_element General Chemistry Alkylation 010402 general chemistry 01 natural sciences Medicinal chemistry Toluene Catalysis 0104 chemical sciences Reaction rate Nickel chemistry.chemical_compound Organic chemistry Oxidative coupling of methane Luzindole |
| Zdroj: | ACS Catalysis. 7:4202-4208 |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.7b01044 |
| Popis: | Nickel-catalyzed oxidative C(sp2)–H/C(sp3)–H coupling of indoles with toluene derivatives is successfully achieved in the presence of 2-iodobutane as the oxidant. This method allows the selective C-2 benzylation of indoles with toluene derivatives over the alkylation with 2-iodobutane and permits the coupling of diversified indoles via the monochelation assistance. The reaction proceeded through a single-electron-transfer (SET) process, wherein both the C–H nickelation of indole and the C–H activation of toluene derivatives have a significant effect on the entire reaction rate. The synthetic utility of this nickel-catalyzed protocol is demonstrated by the facile removal of the directing group and by the convenient synthesis of the melatonin receptor antagonist Luzindole derivatives. |
| Databáze: | OpenAIRE |
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