Gold(I)-Catalyzed Polycyclizations of Polyenyne-Type Anilines Based on Hydroamination and Consecutive Hydroarylation Cascade

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.