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

Journal Article


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.

Publication Date


  • 2016

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84995476562

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/4658

Number Of Pages


  • 9

Start Page


  • 1368

End Page


  • 1377

Volume


  • 5

Issue


  • 11

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.

Publication Date


  • 2016

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84995476562

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/4658

Number Of Pages


  • 9

Start Page


  • 1368

End Page


  • 1377

Volume


  • 5

Issue


  • 11