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KOtBu-Mediated Aerobic Transition-Metal-Free Regioselective β-Arylation of Indoles: Synthesis of β-(2-/4-Nitroaryl)-indoles

Author:
Kumar, Shailesh, Rathore, Vandana, Verma, Ajay, Prasad, Ch. Durga, Kumar, Amit, Yadav, Abhimanyu, Jana, Sadhan, Sattar, Moh., Meenakshi,, Kumar, Sangit
Source:
Organic letters 2015 v.17 no.1 pp. 82-85
ISSN:
1523-7052
Subject:
ambient temperature, chemical reactions, chemical structure, dimethyl sulfoxide, indoles, regioselectivity
Abstract:
A KOᵗBu-mediated intermolecular oxidative C–C coupling of nitroarenes with indoles is presented in DMSO at room temperature in an open flask. By using this mild and economical methodology, syntheses of β-(2/4-nitroaryl)-indoles with sensitive functionalities such as bromo, iodo, cyano, and nitro were achieved chemo- and regioselectively. Synthesized β-(2/4-nitroaryl) indoles were transformed into densely functionalized biindoles, indoloindoles, and (4-aminoaryl)-indoles which demonstrate post-transformation utility of the developed methodology.
Agid:
5788642