On the Gold-Catalyzed Generation of Vinyl Cations from 1,5-Diynes

Abstract

Conjugated 1,5-diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl-substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional approach provided selective access to the angular annulated product in high yield, which was explained by calculations.

Keywords: extended π-systems; gold catalysis; high-energy intermediates; pentalenes; vinyl cations.