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  • Title: Synthetic development and mechanistic study on Pd(II)-catalyzed cyclization of enediynes to benzo[a]carbazoles.
    Author: Chen CC, Chin LY, Yang SC, Wu MJ.
    Journal: Org Lett; 2010 Dec 17; 12(24):5652-5. PubMed ID: 21087056.
    Abstract:
    Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol % of palladium chloride and 2 equiv of cupric chloride in refluxing THF gave benzo[a]carbazoles (6) in good yields. A mechanistic study showed that this reaction must proceed through formation of haloindole (7) followed by a palladium(II)-catalyzed atom transfer cyclization reaction to give the benzo[a]carbazoles.
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