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  • Title: Gold(I)-catalyzed polycyclizations of polyenyne-type anilines based on hydroamination and consecutive hydroarylation cascade.
    Author: Hirano K, Inaba Y, Takasu K, Oishi S, Takemoto Y, Fujii N, Ohno H.
    Journal: J Org Chem; 2011 Nov 04; 76(21):9068-80. PubMed ID: 21951295.
    Abstract:
    A hydroamination-double hydroarylation cascade using aniline derivatives bearing a trienyne moiety as the substrate was efficiently promoted by a gold(I) catalyst to produce benzo[a]naphtho[2,1-c]carbazole derivatives in good yields. This reaction is applicable to various substituted trienyne-type anilines, including 2,3-diethynylthiophene derivatives. The reaction of anilines bearing a tetraenyne and pentaenyne moiety allows direct construction of highly fused carbazoles by tetra- and pentacyclization, respectively, through hydroamination and consecutive hydroarylation without producing any theoretical waste products from the substrates.
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