期刊
ACS CATALYSIS
卷 7, 期 6, 页码 4202-4208出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01044
关键词
benzylation; C-H activation; indoles; nickel; oxidative coupling; pincer complex
资金
- SERB, New Delhi, India [SR/S1/IC-42/2012]
- Alexander von Humboldt Foundation, Germany
- CSIR-New Delhi
Nickel-catalyzed oxidative C(sp(2))-H/C(sp(3))-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.
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