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Palladium(II)‐Catalyzed C3‐Selective Friedel–Crafts Reaction of Indoles with Aziridines
Author(s) -
Yin JieXiang,
Hyland Dr Christopher J. T.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600280
Subject(s) - chemistry , indole test , friedel–crafts reaction , catalysis , substrate (aquarium) , ring (chemistry) , yield (engineering) , medicinal chemistry , palladium , combinatorial chemistry , organic chemistry , oceanography , materials science , metallurgy , geology
The [PdCl 2 (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, [PdCl 2 (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.