Palladium (II) - Catalyzed C3-Selective Friedel-Crafts Reaction of Indoles with Aziridines

Authors

Jiexiang Yin, University of WollongongFollow
Christopher J. T Hyland, University of WollongongFollow

RIS ID

114332

Publication Details

Yin, J. & Hyland, C. J. T. (2016). Palladium (II) - Catalyzed C3-Selective Friedel-Crafts Reaction of Indoles with Aziridines. Asian Journal of Organic Chemistry, 5 (11), 1368-1377.

Abstract

The [PdCl₂(MeCN)₂]-catalyzed C3-selective Friedel-Crafts reaction of 2,2-disubstituted and 2-aryl-N-tosylaziridines with indoles is reported. For the 2,2-disubstituted substrates, [PdCl₂(MeCN)₂] alone, without any ancillary ligands, is an efficient catalyst for the ring-opening reaction. The presence of 1,4-benzoquinone as an additive was found to enhance the ring-opening reaction of the less-reactive 2-arylaziridines. This reaction displayed a broad substrate scope with respect to the indole substrate and is operationally simple. Finally, when 1,3-dimethylindole was employed as a substrate, the de-aromatized pyrroloindoline product was obtained in high yield and good diastereoselectivity.