Pd(0)-Catalyzed (3 + 3) Annulation of Vinylcyclopropanes and Boronic Acid Derivatives: A Route to Vinyltetralones

Abstract

Tetralones play a key role in numerous pharmacologically active compounds and as synthetic intermediates. We report a novel and efficient method for the synthesis of vinyltetralones via a palladium(0)-catalyzed (3 + 3) annulation between vinylcyclopropanes and 2-formyl phenylboronic acid derivatives. This strategy enables the construction of structurally diverse vinyltetralone frameworks under mild conditions. Control experiments were conducted to gain mechanistic insights into the annulation pathway, supporting the involvement of a π-allyl-palladium zwitterionic species in the catalytic cycle. Furthermore, the synthetic utility of the vinyltetralone products was demonstrated through downstream functionalization, highlighting their potential as valuable scaffolds for complex molecule synthesis. This methodology provides a powerful tool for the rapid assembly of tetralone motifs relevant to medicinal and materials chemistry.