KOtBu-Mediated Aerobic Transition-Metal-Free Regioselective β-Arylation of Indoles: Synthesis of β-(2-/4-Nitroaryl)-indoles
Organic Letters2014Vol. 17(1), pp. 82–85
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Shailesh Kumar, Vandana Rathore, Ajay Verma, Ch. Durga Prasad, Amit Kumar, Abhimanyu Yadav, Sadhan Jana, Moh. Sattar, Meenakshi Meenakshi, Sangit Kumar
Abstract
A KO(t)Bu-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.
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