Palladium-Catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes

This report discloses a distinctive palladium-catalyzed sequential tandem cyclization reaction of two molecular haloalkynes and one molecular N-alkylanilines, leading to the efficient assembly of various 3-halo-1,2,5-triarylpyrrole derivatives. Two carbon-carbon triple bonds and one carbon-halogen bond in two molecular haloalkynes are transformed conveniently in one single step, which may involve the aminoalkynylation of haloalkyne and cyclization of the newly formed enyne intermediate. The high chemo-and regioselectivities, good functional group tolerance and late-stage modification of the halopyrrole products further illustrate the synthetic value of this strategy.

Automated summary

This study reports a palladium-catalyzed sequential tandem cyclization reaction that efficiently assembles various 3-halo-1,2,5-triarylpyrrole derivatives through the reaction of two molecular haloalkynes and one molecular N-alkylanilines. The reaction conveniently transforms two carbon-carbon triple bonds and one carbon-halogen bond in one step, showcasing high chemo- and regioselectivities.